Top 50 Vacation Rentals Sheffield (Massachusetts) 2018

AllTheRooms.

Reset Filters

Landmarks & Attractions

Landmarks & attractions

Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Green living at Westwind house on Wolfe SpringFarm
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Breakfast,
Parking
- Details
Description
The Space The room, the bathroom, the living room and the private deck all look out on a stunning vista of mountains and pastures, sometimes with horses grazing. Enjoy the tranquility, the privacy and the knowledge that every watt of energy you use is provided by the sun. The plentiful hot water is also heated by the sun. It's a pleasure to walk around the farm or to the surrounding areas, like the river. You can enjoy home grown...
Amenities
Wifi
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
The Bungalow in Sheffield MA (The Berkshires)
2br Bungalow
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Breakfast,
Parking
- Details
Description
The Space This single level 1,250 square foot renovation provides an open plan Great Room that measures 18 x 24 feet or 432 sq. feet. The living/TV area is spacious, comfortable and relaxing with a queen size convertibles couch and two antique club chairs, an adjustable wing chair, vintage side and coffee tables and a flat screen TV connected to SPECTRUM Cable TV and Wi-Fi along side is the dining area with Art Deco style table & chairs under a...
Amenities
Wifi
Breakfast
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Large Log Cabin near Great Barrington & Lakeville
4br Cabin
4 Bedrooms
3 Bathrooms
12 Sleeps
Wifi,
Gym,
Pets OK,
Parking
- Details
Description
The Space Our cabin is a combination of classic New England cottage charm with modern mid-century touches. For people looking to have fun and relax we have a foosball table, pool table, yoga studio and two hammocks that hang over the covered front porch. Enjoy your morning coffee or tea on the back deck listening to the birds sing and trees dancing in the wind. Finally, for those that remember or appreciate board games, we have a pantry stocked with games...
Amenities
Wifi
Gym
Pets OK
Parking
Additional info
Bedrooms:4
Sleeps:12
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Comfortable Apartment sleeps two.
1br Home/Apartment
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space We are in a rural area. Our home is on a quiet, residential road and we reside in the main house. The apartment comfortably accommodates one or two people. With a covered porch to sit in the morning with coffee and in the evening to reflect on the day as the sun set. There are many attractions to take advantage of especially if you like the outdoors, great restaurants and quaint New England towns like Great Barrington, Stockbridge and...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
The Pottery Barn Room at Buttonwood
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Breakfast,
Parking,
Pool
- Details
Description
The Space Located on the second floor front corner room of Buttonwood. It has a full size bed with sitting area, private bath and shower. Wonderful view of back pool area, acrage, frog pond, grape arbor, also view of Buttonwood front lawn. We are 2 1/2 hours from Boston and 2 hours from NYC. (Wassaic NY commuter rail to Grand Central Station is 25 minutes drive) The property has many things available for your comfort and enjoyment. In Summer an...
Amenities
Wifi
Breakfast
Parking
Pool
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
The perfect Berkshire getaway!
2br Other
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space This perfect Berkshire retreat on beautifully landscaped grounds is the ultimate escape. Vacation in style in this tastefully renovated cottage. Entertain in the open gourmet kitchen or spread out onto the back deck for grilling or relaxing in the beautiful gardens. Hangout and spend the day enjoying the private grounds and beautiful perennial plantings. The picturesque roads of Sheffield offer some of the best biking in New England. A stones throw from the Appalachian Trail among many other ideal...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Hideaway with Spectacular Berkshire Views
1br Other
1 Bedroom
1 Bathroom
3 Sleeps
Wifi,
Breakfast,
Parking
- Details
Description
The Space Your stay includes fresh organically grown vegetables and flowers ( in season) from our vegetable garden with fresh eggs from our chickens and honey from our resident beehive. A refugee from the busy world this charming private living space makes mornings relaxing as you enjoy a stocked cupboard of breakfast supplies including locally roasted specialty coffee, Harney and Sons Teas, local Bola Granola from Berkshire artisans in addition to our home grown hospitality. Flax linen coverlet,...
Amenities
Wifi
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:3
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Comfy Tranquil Bedroom/Bathroom in the Berkshires
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space In our home, you will enjoy the private upstairs master bedroom and bathroom, with access to our kitchen. *UPDATE* [We recently opened a second guest room in our home so you might be sharing the bathroom with another guest please feel free to ask in advance if there will be another guest staying in our second room if this is an issue for you] We keep mostly downstairs in our basement. The bedroom is fully-furnished with a queen-sized pillow-top mattress bed, lounge...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Nantucket Suite at Buttonwood
2br Bedroom
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Breakfast,
Parking,
Pool
- Details
Description
The Space Very nice room with two windows overlooking Berkshire Mts. Queen size antique bed, sitting area, desk, bureau with large mirror and drawers, also has a small bedroom with a full bed and both share a private bath. Total access to wireless internet. "Buttonwood" a revolutionary war era Georgian/Federal country home is named after the large centuries old Sycamore tree in its front yard; one of the largest in Massachusetts. This bucolic setting, surrounded by 60 acres of corn...
Amenities
Wifi
Breakfast
Parking
Pool
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Apple Cottage on Wolfe Spring Farm.
3br Farm Stay
3 Bedrooms
3 Bathrooms
9 Sleeps
Parking,
Wifi
- Details
Description
Originally built by a stonecutter in 1840, Apple Cottage, completely renovated in 2015, is a charming historic home in the orchard of a working organic farm. The farmers/ hosts like to provide you with farm fresh eggs and berries in season. Comfortable, thoughtful amenities include pillow top mattresses, smart TV, wireless, jet tub, floor heat in bathrooms, a boot room for skis and bikes which includes a laundry; Views from every window. Chef's kitchen with walk-through pantry to...
Amenities
Parking
Wifi
Additional info
Bedrooms:3
Sleeps:9
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Apple Cottage: Baldwin Suite
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Parking
- Details
Description
The Space The Baldwin Suite is one of three suites in Apple Cottage and one of four suites on the farm. The Baldwin is a first floor suite with a brand new double pillow top bed. It has an ensuite bath with shower and a coffee bar. Guest Access You have access to a comfortable living room with smart TV, a huge deck, a chef's kitchen a dining room with a farmhouse table and a large vestibule where you can store your bike,...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Berkshire Monarch Hill Retreat , Pool, Views, Secluded Setting, Immaculate!
4br Retreat
4 Bedrooms
4 Bathrooms
8 Sleeps
Parking,
Wifi
- Details
Description
At an elevation of 300 feet above the valley, this house boasts one of the most inspiring and expansive views in all of the Berkshires. Private and secluded, the 42 acre parcel is nestled inside Bartholomew's Cobble, a 329 acre bird sanctuary with abundant walkways through fields of wild flowers, and 5 miles of family friendly well maintained trails with limestone outcroppings along the Housatonic River . Grab a blanket and a basket of goodies for a 5 minute hike...
Amenities
Parking
Wifi
Additional info
Bedrooms:4
Sleeps:8
Bathrooms:4
Rating Overall Score99%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Apple Cottage: The Juliet Suite
Bedroom
1 Bedroom
1 Bathroom
3 Sleeps
Wifi,
Parking
- Details
Description
The Space The Juliet Suite looks out over the orchard and pasture on Wolfe Spring Farm, a working organic farm in bucolic Sheffield. A great location to get to Tanglewood, Sharon Playhouse, the appalachian trail, Bartholomew's Cobble, Shakespeare and Company, Great Barrington and Mahaiwe Theatre OR stay on the farm and hike, bike, fish, canoe or pick fruit. Guest Access You have access to a comfortable living room, a huge deck, a chef's kitchen a dining room with a farmhouse table and a...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:3
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Gorgeous Sheffield Home in Heart of Berkshires
5br Home/Apartment
5 Bedrooms
4 Bathrooms
16 Sleeps
Parking,
Wifi
- Details
Description
Our home is a beautiful mountain-style home (exposed beams, wood floors, all new appliances) on a quiet rural road with commanding views of the Housatonic valley and Mt. Everett. Six miles to Great Barrington in the heart of the Berkshires. The house has five bedrooms, two living rooms, loft area and 3.5 bathrooms. We have a wrap-around deck, screened porch, outdoor fire pit and charcoal grill. The home sits on 5 lush acres up a long private...
Amenities
Parking
Wifi
Additional info
Bedrooms:5
Sleeps:16
Bathrooms:4
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
The Mews at Buttonwood
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Breakfast,
Parking,
Pool
- Details
Description
The Space Quaint bedroom with two single beds, private bath with great shower, is on ground floor, next to large family room with large sitting area and main fireplace of the home. Its a really special place . "Buttonwood" a revolutionary war era Georgian/Federal country home located in the village of Ashley Falls, Ma. is named after the large centuries old Sycamore tree in its front yard; one of the largest in Massachusetts. This bucolic setting, surrounded by 60 acres of...
Amenities
Wifi
Breakfast
Parking
Pool
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Gorgeous Sheffield Home
5br Home/Apartment
5 Bedrooms
4 Bathrooms
15 Sleeps
Wifi,
Parking
- Details
Description
The Space Our home is a sparkling mountain style house with two master bedrooms, two kitchens, two large living rooms, a farmhouse kitchen table that seats 20, immense wrap-around deck with bbq and dining table, screened porch and endless views of the Berkshire mountains. Guest Access Guests have access to the whole house with use of canoe ...
Amenities
Wifi
Parking
Additional info
Bedrooms:5
Sleeps:15
Bathrooms:4
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Comfortable Berkshire Getaway
3br Other
3 Bedrooms
3 Bathrooms
6 Sleeps
Wifi,
Parking
- Details
Description
The Space The open floor plan, updated kitchen and comfortable living room make this a great place to relax with friends and family. Guest Access The full property is available to our guests during their stay. This includes a lovely lawn and stone patio. Interaction with Guests We are not on site during our guests' stay but we are available as needed for recommendations or to help with any issues that may arise. ...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Perfect Berkshires Getaway!
2br Cottage
2 Bedrooms
1 Bathroom
4 Sleeps
Parking,
Wifi
- Details
Description
This perfect Berkshire retreat on beautifully landscaped grounds is the ultimate escape. Vacation in style in this tastefully renovated cottage. Entertain in the open gourmet kitchen or spread out onto the back deck for grilling or relaxing in the redwood hot tub. Hangout and spend the day enjoying the private grounds and beautiful perennial plantings. The picturesque roads of Sheffield offer some of the best biking in New England. A stones throw from the Appalachian Trail among many other ideal...
Amenities
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score92%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Apple Cottage: Empire Suite
Bedroom
1 Bedroom
1 Bathroom
3 Sleeps
Wifi,
Parking
- Details
Description
The Space The Empire Suite looks out over the mountains surrounding Wolfe Spring Farm, a working organic farm in bucolic Sheffield. A great location to get to Tanglewood, Sharon Playhouse, the appalachian trail, Bartholomew's Cobble, Shakespeare and Company, Great Barrington and Mahaiwe Theatre OR stay on the farm and hike, bike, fish, canoe or pick fruit. Guest Access You have access to a comfortable living room, a huge deck, a chef's kitchen a dining room with a farmhouse table and a large...
Amenities
Wifi
Parking
Additional info
Bedrooms:1
Sleeps:3
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
House Among Trees - A Perfect Getaway
3br Home/Apartment
3 Bedrooms
2 Bathrooms
6 Sleeps
Wifi,
Parking
- Details
Description
The Space The house is built in 1977 and carries some of the mid century flavor of clean lines and the charm of natural materials. With skylights in the living room and plenty of windows throughout the house, you feel one with nature that surrounds the house. The grounds are plentiful with tall evergreens. Enjoy the sauna or take a walk down the path to the clearing downhill. Start a fire in the pit, roast marshmallows and gaze at the stars....
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:2
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Lovely 3-Bedroom Berkshire Retreat
3br Bedroom
3 Bedrooms
3 Bathrooms
6 Sleeps
Wifi,
Parking
- Details
Description
Charming, quiet 3-bedroom, 2.5-bath home at the edge of the woods in the bucolic Berkshires. Sleeps five, (air mattress for a sixth). Wifi, basic cable & plenty of parking. Perfect retreat for writers, artists or musicians; has a baby grand piano. Catamount and Butternut ski areas both 20 minutes away. Wonderful hiking trails and lakes all around us. Berkshire Choral Festival is down the street. Berkshire Theater Group, Tanglewood, Shakespeare & Company, Kripalu Center for Yoga, Jacob's Pillow...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
See individual room listings for prices.
3br Bedroom
3 Bedrooms
3 Bathrooms
8 Sleeps
Wifi,
Breakfast,
Parking,
Pool
- Details
Description
Three rooms available- Each with private baths. Rooms starting at $125.00 for "The Mews at Buttonwood" per night, the "Pottery Barn Room at Buttonwood" $150.00 per night and the "Nantucket Suite at Buttonwood" $200.00....
Amenities
Wifi
Breakfast
Parking
Pool
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Apple Cottage at Wolfe Spring Farm
3br Farm Stay
3 Bedrooms
3 Bathrooms
9 Sleeps
Wifi,
Parking
- Details
Description
The Space We provide charm, comfort and cleanliness and we provide for every little need. The pantry is stocked with staples and you will find our farm fresh eggs in the fridge. Guest Access The entire house welcomes you including a very large deck, a dining room that seats 12, a mudroom with plenty of storage for bikes, skis or even a kayak (and a laundry room), a chef's kitchen with a walk-through pantry and a very comfy living room with a...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:9
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
238 Main, Sheffield, MA, the Berkshires.
2br Other
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
1869 Italianate/Greek revival home with a 2 bedroom apartment at the rear of the house. ALSO SEE STUDIO LISTING The apartment has been totally renovated with a private terrace overlooking the garden. Queen size beds, and a fully equipped kitchen. Berkshire coffee/decaf, teas, milk and juice are a welcome gift. No searching for the nearest coffee shop on the first morning. The bathroom has radiant heat, a towel warmer, bathrobes and toiletries. 238 is in the heart of the Berkshires. Come visit!...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Amazing Loft
3br Home/Apartment
3 Bedrooms
3 Bathrooms
6 Sleeps
Wifi,
Gym,
Parking
- Details
Description
A sleek and spacious residence set atop a treasured textile design studio, surrounded by serene river run fields and mountain views. A grand chefs kitchen balances an indoor/outside living space with a glass garage door opening to an outdoor oasis. Master bedroom has it's own sun porch and skylighted bath. Stylized Bed 2 w/bath en-suite. Bed 3's private 'tower' and Bed's 4's lofted, open layout offer desired flexibility. Creative and Modern - when you...
Amenities
Wifi
Gym
Parking
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Renovated Farmhouse with Terrific Views, Fire pit, and Big Views!
5br Farmhouse
5 Bedrooms
3 Bathrooms
11 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Amenities: 5 bedrooms 2.5, baths - sleeps 11, AC for all bedrooms, Wi-Fi internet, cable TV with Premium Channels/HBO, wood-burning fireplace, steam shower, mountain and pastoral views, 8 acres, 2-car garage, Teepee, fire pit, tree swing, Weber grill, mountain bikes and cross-country skis (sizes not guaranteed!) + 2 kayaks! NO SMOKING and pets are considered. RENTER PAYMENT INFORMATION: -eCheck: Renter is responsible for the additional 3% eCheck processing fee when booking through this site. -Credit Card: Renter is responsible for the...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:5
Sleeps:11
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Comfortable Sheffield Home
3br Bedroom
3 Bedrooms
2 Bathrooms
3 Sleeps
Wifi,
Parking
- Details
Description
The Space Guests are welcome to use the entire house. Main floor bedroom has private bath and upstairs bedrooms share bath. I can book your choice of main floor or upstairs, and willing to consider all beds for a family. Price per room/ additional room(s) on request. ...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:3
Bathrooms:2
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Apple Cottage
3br Cottage
3 Bedrooms
6 Bathrooms
- Details
Description
Charmingly restored 1840 cottage in the apple orchard of a working organic farm. Completely renovated in 2015 with thoughtful amenities, fresh eggs and produce and acres of trails and views. Close to waterfalls and lakes. Nearby ski hills, Tanglewood concerts, theatre, film festival, dance and botanical gardens....
Additional info
Bedrooms:3
Bathrooms:6
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Renovated Country Home in Berkshires - Views
3br Home/Apartment
3 Bedrooms
3 Bathrooms
7 Sleeps
Wifi,
Parking
- Details
Description
The Space Completely renovated throughout, with new kitchen, hardwood floors, spacious and light-filled great room with fireplace, 3 bedrooms, 3 full bathrooms (including en suite master bedroom with fireplace). Big screened-in porch (converted to glassed-in during winter) and large deck. Great fire pit with mountain views. On two acres, fully private, secluded location. Guest Access Near hiking and biking trails, skiing, antiquing, the best of Berkshires, Columbia County, NY and Litchfield County, CT. Interaction with Guests We live in NJ and have a caretaker...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:7
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Beautiful,Berkshire,(3+) bedroom home Close to All Summer Attractions &Skiing
3br Bedroom
3 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Family or Lovers getaway! 3 bedrooms plus library, Sleeps 6-8 A beautiful 6 year old, 3050 Sq. Ft. , 2-Story Colonial and attached 2 car garage. Large, glamorous, open, chefs kitchen where everything is first class. Marble counters. Professional Blue Star (6 burner) gas range. Fully stocked kitchen with all kitchen tools! Close to Great Barrington, Stockbridge & Lee Outlet Mall! Close to Butternut& Catamount & a 45 min. drive to Jiminy Peak! enjoy the steam shower or...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Serene, updated home on 5 acres, 5 min to town
4br Home/Apartment
4 Bedrooms
3 Bathrooms
8 Sleeps
Wifi,
Parking
- Details
Description
The Space Situated on 5.3 acres of land, this very private, country-contemporary home has 5 bedrooms and 3 bathrooms & a screened in porch which can be enjoyed during any time of year. The living room is fully equipped with a LED Smart TV, equipped with Netflix and cable TV service. Guest Access You will be welcome to have access to use the entire space and outdoor areas. Please use caution when hiking outdoors in the forestry areas. Avoid the times of dawn...
Amenities
Wifi
Parking
Additional info
Bedrooms:4
Sleeps:8
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Elegant Berkshire Vacation Rental
3br Home/Apartment
3 Bedrooms
3 Bathrooms
6 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space This property is in the highly sought after Bershire Vacation area for your year round summer, fall foliage and winter wonderland vacations. A very short drive to skiing at Butternut & Catamount. If you like shopping you are just minutes from Lee Outlet Mall. Historic Stockbrige is nearby. Summer rentals feature Tanglewood, Shakespeare Festival, hiking and kayaking. Great biking! Close to Lime Rock racing. Guest Access Guests will have access to entire house. Interaction with Guests Owner will correspond with renters...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Newly Renovated Country Retreat
3br Retreat
3 Bedrooms
3 Bathrooms
7 Sleeps
Parking,
Wifi
- Details
Description
A private, peaceful getaway nestled in the Southern Berkshires. Our fully renovated country home has a small orchard, and is surrounded by farmlands, hundreds of acres of nature preserves and sweeping views of the Taconic and Berkshire Mountains. We're a 2.5 hour drive from NYC. Our home was completely renovated in 2015 and features a terrific big screened-in porch (that is converted to glass windows during colder seasons) with dining and lounging areas, and a large deck with a grill...
Amenities
Parking
Wifi
Additional info
Bedrooms:3
Sleeps:7
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Beautiful Mountainside House with nearby Lake and Hiking Trails
3br Home/Apartment
3 Bedrooms
2 Bathrooms
8 Sleeps
Parking,
Wifi
- Details
Description
Our secluded property is a great place to relax and enjoy the company of your friends and family. The house has all the amenities: well-equipped kitchen, fireplace, sauna, ping-pong table, patio and an outdoor fire pit. Sheffield is a paradise for antique lovers. Checkout Local Art Galleries, Rockwell museum, Tanglewood, Hancock Village. Explore a range of old and new restaurants. Lakeville is a treat with it's sandy beach and scenic vews....
Amenities
Parking
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:2
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
The perfect Southern Berkshire winter vacation esc
4br Other
4 Bedrooms
2 Bathrooms
- Details
Description
This beautiful and secluded winter utopia is perfect for your Berkshire winter vacation getaway. Private and secluded, this home is nestled on five private acres in the woods located conveniently within fifteen minutes to many area attractions. Wether you are looking to ski the slopes, capture the performing arts experience, relax around the outdoor fireplace or enjoy the large winter porch sipping on hot chocolate- you will not be disappointed! With 4 bedrooms and 2 bathrooms, this 4,800 square foot home...
Additional info
Bedrooms:4
Bathrooms:2
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Staveleigh House Bed and Breakfast
7br Bed & Breakfast
7 Bedrooms
18 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
id="propery-desc">Staveleigh House Bed and Breakfast is conveniently located on Route 7 in historic Sheffield, Massachusetts. Our comfortable and affordable B&B has 7 rooms all with private baths. We’re just minutes away from many fine restaurants and shopping in Great Barrington and close to major Berkshires attractions. The rooms are Queen, King and Twin bedded, all are air conditioned and most have cable TV. WiFi is available throughout the inn. Breakfast features fresh roasted coffee, seasonal fruit and a hearty entree. ...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:7
Sleeps:18
Rating Overall Score98%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Good
Artist Cottage with a view in Berkshires
3br Cottage
3 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Breakfast,
Parking
- Details
Description
The Space It is unique because it has an artist studio. ...
Amenities
Wifi
Breakfast
Parking
Additional info
Bedrooms:3
Sleeps:4
Bathrooms:1
Rating Overall Score90%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Good
Retro Rustic Berkshires Apartment
2br Home/Apartment
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space It has a remodeled kitchen that opens into a dining area. This living room has a brick wall and mid mod furnishings. It has a small bathroom with a hot shower. Both bedrooms have comfy beds. Next door is the famed Racebrook Lodge and our guests get a 10% discount at their farm to table restaurant. Stroll along the trails and enjoy live music on thursday evenings. Guest Access The grounds are shared including the fire pit, tiki bar, grill,...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score90%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Good
Red Door 23
3br Other
3 Bedrooms
1 Bathroom
7 Sleeps
Breakfast,
Parking
- Details
Description
The Space Red Door 23 has an open floor plan to allow for easy entertaining between the kitchen and the living space. A small wood stove creates ambiance in the winter, and giant sliding glass doors create easy indoor-outdoor living in the summer. The three spacious bedrooms are sunny and clean with simple decor. A large and lush backyard provides space for kids, gardening, and grilling. The Berkshires is the ideal setting to reconnect with nature while still having access to...
Amenities
Breakfast
Parking
Additional info
Bedrooms:3
Sleeps:7
Bathrooms:1
Rating Overall Score90%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Good
Boardman Views
5br Other
5 Bedrooms
3 Bathrooms
11 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space Boardman Views is a beautifully updated farmhouse located in a spectacular Northern Sheffield rural neighborhood overlooking pastures with a spectacular view of Mount Washington! The home is located on eight acres of land and has a large fire pit and a small entertaining shed called the chicken coop which invites renters to walk around the land and enjoy this lovely natural "Berkshire" environment. Inside: One enters through the sunny renovated boot-room with stone floor, which also serves as...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:5
Sleeps:11
Bathrooms:3
Rating Overall Score90%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Sweet retreat--cabin on organic farm.
1br Retreat
1 Bedroom
1 Bathroom
2 Sleeps
Parking
- Details
Description
The Space Not really camping... The farm's cabin has been spiffed up for guests with a comfy double bed, a window seat and a small table for writing or just coffee. This one room cabin on short stilts sits slightly uphill from the farmstead. Fully screened, (bring your sleeping bag or comforter for brisk nights) it's a wonderful, quiet perch from which to hear, smell, watch and enjoy farm life. Though you can recharge your laptop or phone, there's no internet...
Amenities
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Elterwater--Sought after and rare idyllic Berkshire lakefront in Sheffield.
3br Other
3 Bedrooms
2 Bathrooms
4 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Perfect location for all Berkshire activities. Light-filled, year-round lakefront house, with fireplace, all newly-furnished and decorated in mid-century retro style. Think 'Walden,' think 'On Golden Pond.' Two bedrooms with A/C—one queen-sized bed, two twins (new) two full baths, living room with fireplace, dining area, kitchen with dishwasher and microwave, den with pull-out couch, water softener, plus screened in porch, full laundry room, two car garage--and all on the most blissful private 150 acre lake with wonderful...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:4
Bathrooms:2
Rating Overall Score99%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Beautiful House, Featured in 'Country Living' Magazine
3br Home/Apartment
3 Bedrooms
2 Bathrooms
6 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Master bedroom suite has king-size bed and master bath has separate tub & shower. Spacious great room combines living room with a great stone fireplace, dining room & chef's kitchen under cathedral ceiling. Kitchen's equipped with Viking and Sub-Zero appliances. Back wing features 2 spacious bedrooms with 1 1/2 baths. French doors and decks accessible from every room. House is situated on 9 beautiful acres bordered by the Konkaput River with a close-up view of the Ashley Falls Waterfalls....
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:2
Rating Overall Score97%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Comfortable Berkshire Getaway
3br Other
3 Bedrooms
3 Bathrooms
6 Sleeps
- Details
Description
A comfortable 3 bedroom 2.5 bath house great for families or couples. The newly renovated kitchen is open to the living room providing a bright and airy feel. All the modern comforts are available: air conditioning, WiFi, Apple TV, washer/dryer. Out front enjoy rocking on the front porch or head to the back, off the kitchen, where a newly installed blue stone patio leads into plenty of lawn for kids to play and edged by woods. Neighbors...
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Spacious 6 BR Country Retreat With Secluded Tree Top Mountain Views
6br Retreat
6 Bedrooms
5 Bathrooms
12 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Extraordinary, recently renovated home set high on 23 acres of open rolling lawn with extensive distant mountain views. The front door is a replica of the front door at the Mission House in Stockbridge. Bright, renovated kitchen has a fireplace with a beehive oven, wide pine floors, and hand-hewn pine cabinets. A center stove-top island and back staircase complete a very cozy spot to gather with your family and/or guests. Dining room with surrounding mountain, a 20'x40' in-ground swimming pool...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:6
Sleeps:12
Bathrooms:5
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Brand new Berkshire home-Perfect getaway house for friends and families
3br Home/Apartment
3 Bedrooms
3 Bathrooms
9 Sleeps
Parking,
Wifi
- Details
Description
This is a brand new renovated house from top to bottom! It has fantastic large windows with lots of natural sunlight, all wood floors and new appliances. There is lots of room for cooking and entertaining inside and out. We have a wrap around deck with a large open and wooded yard (2+ acres) which includes a bon-fire ring with chairs, dining table and gas grill. Great for play outside. Inside has a gas fireplace in...
Amenities
Parking
Wifi
Additional info
Bedrooms:3
Sleeps:9
Bathrooms:3
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Sweet Cottage Stay on Working Organic Farm in The Berkshires, Massachusetts
1br Farm Stay
1 Bedroom
9 Sleeps
Wifi
- Details
Description
This sweet cottage rental makes for the ideal farm stay getaway on a working organic farm in The Berkshires of Massachusetts, and it can accommodate up to nine guests. There are three bedrooms total. The 'Empire Suite' comes with a queen-size bed and a twin daybed, as well as a coffee bar. The 'Julian Suite' features a queen-size bed and a twin daybed with a trundle bed in the sitting room, as well as a coffee bar. The 'Baldwin Suite'...
Amenities
Wifi
Additional info
Bedrooms:1
Sleeps:9
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Staveleigh House Bed and Breakfast
7br Bed & Breakfast
7 Bedrooms
Breakfast,
Parking,
Pets OK,
Wifi
- Details
Amenities
Breakfast
Parking
Pets OK
Wifi
Additional info
Bedrooms:7
Rating Overall Score94%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Excellent
Cozy Berkshire Stay
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Smoking,
Pets OK,
Breakfast,
Parking
- Details
Description
House is situated in a private location in the Berkshire’s with plenty to do. Hiking, biking, museums, theater, Tanglewood, antique shops, and a wide variety of restaurants!...
Amenities
Smoking
Pets OK
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
Oops! this property is not available now. Fortunately we have other great options.
This property may have been deactivated by the owner, check other great options in the list below.
Checking availability...
Nice
Cozy Berkshire Stay!
Bedroom
1 Bedroom
1 Bathroom
2 Sleeps
Wifi,
Smoking,
Pets OK,
Breakfast,
Parking
- Details
Description
Guest Access Guests have access to kitchen, living room and laundry room! ...
Amenities
Wifi
Smoking
Pets OK
Breakfast
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score80%

Scanning 16,103,039 couches, castles, rooms, apartments, boats and more

“There is no room on the planet that matches your search. Please try changing the selected filters”

Reset filters

The Best Sheffield Vacation Rentals (Massachusetts) in September 2018

Cities near Sheffield

Top 10 cities in United States of America

Rentals in Sheffield