Top 50 Vacation Rentals Oakland (Maryland) 2018

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Oakland, Maryland Travel Guide

Oakland is a small town in the Western reaches of Maryland, and while it may be sleepy by nature, it's only a car ride away from a variety of locations like Pittsburgh to the north, Morgantown, West Virginia to the west, and Washington DC to the east. With an all-American feel and historic, old buildings lining the main roads, Oakland is a picturesque place to see.

Things to do in Oakland, Maryland

Oakland is home to a popular railroad museum, outlining its involvement with the B&O Railroad. Oakland is also close to a number of beautiful outdoor destinations like Swallow Falls State Park and Herrington Manor State Park.

Best Time to Visit Oakland, Maryland

Fall is a lovely time to visit as the weather still holds above freezing levels and visitors can admire the changing colors of autumn.

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Nice
Alpine Lake Resort
5br 3-star Hotel
5 Bedrooms
Gym,
Parking,
Pets OK,
Pool,
Wifi
- Details
Description
Get an overview of this hotelFamily-friendly lodge with golf course and restaurant Location This family-friendly Terra Alta lodge is located on a lake, 7.8 mi (12.6 km) from Cranesville Swamp Natural Area, and within 20 mi (32 km) of Hovatter's Wildlife Zoo and Cathedral State Park. Deep Creek Lake State Park and Wisp Resort are also within 25 mi (40 km). Property Features This smoke-free lodge features a golf course, a restaurant, and an indoor pool. Free WiFi in public areas and free...
Amenities
Gym
Parking
Pets OK
Pool
Wifi
Additional info
Bedrooms:5
Rating Overall Score72%
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Good
The Garrett Inn
10br 2-star Hotel
10 Bedrooms
Parking,
Wifi
- Details
Description
Get an overview of this hotelMotel in Oakland with free parking Location Situated in Oakland, this motel is 4.7 mi (7.6 km) from Deep Creek Lake State Park and within 12 mi (20 km) of Wisp Resort and Thousand Acres Lakeside Golf Course. Cranesville Swamp Natural Area is 11.9 mi (19.2 km) away. Property Features Free self parking and free WiFi in public areas are available at this motel. Room Amenities All 10 rooms provide conveniences like refrigerators and microwaves, plus free WiFi and...
Amenities
Parking
Wifi
Additional info
Bedrooms:10
Rating Overall Score84%
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Excellent
Haley Farm Bed & Breakfast
2br Bed & Breakfast
2 Bedrooms
4 Sleeps
- Details
Description
id="propery-desc">Haley Farm Inn and Retreat Center is located in the mountains of Western Maryland, minutes from Deep Creek Lake, WISP ski and golf resort, and five state parks. The Inn is only 3 hours from the Washington DC area, and 2 hours from Pittsburgh. "Weekenders are advised to stay at Haley Farm" Washingtonian Magazine. Haley Farm is beautifully decorated with tapestries, antiques and art from around the world. Most of the suites suites (there are nine)...
Additional info
Bedrooms:2
Sleeps:4
Rating Overall Score92%
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Excellent
Captivating 2 Bedroom cottage with hot tub offers amazing river access!
2br Bedroom
2 Bedrooms
1 Bathroom
6 Sleeps
Wifi
- Details
Description
Rich in Deep Creek history, this cottage was built as company housing for Deep Creek's Hydro Electric Dam workers in 1925. Featuring private Youghiogheny River frontage in the protected Wild and Scenic Corridor, this home is completely unique in Deep Creek. Private yet within a five minute drive to Wisp skiing, lake activities and Fork Run's hiking, mountain biking and rock climbing. Want to stay at home? Just bring your fly rod, walk down your private access and in seconds...
Amenities
Wifi
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:1
Rating Overall Score91%
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Excellent
Gorgeous 7 Bedroom Central-Lake w/Dock Slip; Beautiful Sunrises from the Deck
7br Bedroom
7 Bedrooms
7 Bathrooms
18 Sleeps
Wifi
- Details
Description
If you are seeking a large spacious lakefront home, brimming with all desirable amenities, then we have the perfect home for you. Wynsome Run Lodge is a spectacular 7 bedroom home ideally located close to Deep Creek State Park, a movie theater, and area restaurants. The expansive Great Room, beautifully adorned with a large stone fireplace and hardwood floors, showcases a spectacular lake view. Not only is there ample room for everyone to spread out, but there are plenty of...
Amenities
Wifi
Additional info
Bedrooms:7
Sleeps:18
Bathrooms:7
Rating Overall Score91%
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Excellent
Cottage on the Farm* unwind and be close to nature
1br Farm Stay
1 Bedroom
1 Bathroom
4 Sleeps
Smoking,
Parking
- Details
Description
The Space This one room rustic cabin is located in the heart of the farm near our house and barn. Converted from a x-c ski lodge, this spacious cabin gives you room to spread out. Plenty of space to relax on the large front porch with a gorgeous view. Includes mini fridge, microwave, stereo, games, simple fishing gear and some of our favorite books for lazy day reading. We provide a coffee maker and electric kettle, fresh coffee and tea. There...
Amenities
Smoking
Parking
Additional info
Bedrooms:1
Sleeps:4
Bathrooms:1
Rating Overall Score100%
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Excellent
Secluded Lakefront Log Home w/ Hot Tub and Private Dock!
5br Home/Apartment
5 Bedrooms
5 Bathrooms
12 Sleeps
Wifi
- Details
Description
Surround yourself with nature in this majestic log home. Three master suites make it an excellent choice for couples as well as family gatherings. On the entry level, hardwood floors, cathedral ceilings and large windows adorn the great room, and the stone fireplace and stylish furnishings accent the warmth of these rooms. An open layout makes it easy to enjoy the company of family and friends when you are making a home cooked meal in the well-equipped kitchen. The island...
Amenities
Wifi
Additional info
Bedrooms:5
Sleeps:12
Bathrooms:5
Rating Overall Score97%
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Nice
Cute & Inviting 3 Bedroom with an incredible lakefront!
3br Cottage
3 Bedrooms
2 Bathrooms
8 Sleeps
Wifi
- Details
Description
Do you find yourself daydreaming about a romantic getaway in a charming lakefront home? Golden Retreat is perfect for a couple but is large enough for a small family. You'll adore the comfortable furnishings and alluring appeal of the interior. Conveniently located a mere 5 minutes from Swallow Falls State Park, you will love coming home to relax on the screened porch after a day of hiking. Summer fun will surely be had by the whole family as you spend...
Amenities
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:2
Rating Overall Score79%
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Excellent
TRANQUIL & PRIVATE 5 Star Cabin w/ OUTDOOR FIREPLACE , XL HOT TUB & POOL TABLE
5br Hotel
5 Bedrooms
4 Bathrooms
14 Sleeps
Gym,
Parking,
Wifi
- Details
Description
Architecturally pleasing to the eye and the soul, this UNIQUE AND GORGEOUS 'GREEN HOME' boasts a 31' great room ceiling with 2 INTERIOR and 1 EXTERIOR (on deck) ///W@@D BURNING\\\ STACKED STONE FIREPLACES (also 31' tall) plus LARGE HOT TUB ON DECK and LARGE FIRE PIT in back yard. This luxury Deep Creek Lake cabin is very private, yet close to all Deep Creek activities and attractions. This serene gem backs to a hemlock and boulder forest...
Amenities
Gym
Parking
Wifi
Additional info
Bedrooms:5
Sleeps:14
Bathrooms:4
Rating Overall Score98%
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Good
Picturesque 2 Bedroom Cottage in peaceful setting!
2br Cottage
2 Bedrooms
2 Bathrooms
8 Sleeps
Wifi
- Details
Description
Nestled in the woods, Hideaway is an adorable A-frame mountain chalet that is the perfect getaway for a small family or a couple's retreat. Recently renovated, this home offers a cozy Great Room with stylish furnishing and glistening hardwood floors. Family time will be spent watching your favorite movies on the large flat screen TV or prepare your families favorite meals in the fully stocked kitchen. In addition to a full bathroom you will also find a beautifully decorated bedroom...
Amenities
Wifi
Additional info
Bedrooms:2
Sleeps:8
Bathrooms:2
Rating Overall Score85%
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Excellent
Casa Cossick
2br Other
2 Bedrooms
1 Bathroom
6 Sleeps
Wifi,
Parking
- Details
Description
The Space The best view that doesn't cost a million dollars. Private deck, free Wifi, HD TV, jacuzzi tub, 2 bedroom, 1 large bathroom, fireplace, oven, microwave, fridge, dressers, closets, washer/dryer, ample parking, (Hidden by Airbnb) Chromecast. Guest Access You can have access to the entire home. Interaction with Guests I will only be a call or text away throughout your stay. The Neighborhood Quiet and safe neighborhood. Getting Around Ample parking right outside the front door. ...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:1
Rating Overall Score100%
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Excellent
Glamping - Cozy Hut - Uzes
Hut
6 Bathrooms
4 Sleeps
Pets OK,
Parking
- Details
Description
The Space 300 acres of private land, with miles of groomed trails and access to the Youghiogheny River. Right next door to Sate Parks and State Forest and just a 10 minute drive from Deep Creek Lake. There are 5 huts available and listed separately. Glamping hut Stanley also has a tipi beside it which you can rent for an additional fee - it's a great space for kids. Please check all listings for availability. It is...
Amenities
Pets OK
Parking
Additional info
Sleeps:4
Bathrooms:6
Rating Overall Score100%
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Excellent
Winter is Coming
3br Other
3 Bedrooms
3 Bathrooms
8 Sleeps
Wifi,
Parking
- Details
Description
The Space 10 min drive to Wisp Fire wood present Indoor hot tub Walking distance to Dutch's at Silver Tree Guest Access The entire house is available to my guests. Interaction with Guests I am available by phone text or email at all times. The Neighborhood Private Court plenty of parking Getting Around Very short ride to Pizza Uno's Other Things to Note Guests will be given instructions on entry a few days before check in. ...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score100%
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Good
Wonderful 5 Bedroom Lakefront home with outdoor hot tub & private dock!
5br Bedroom
5 Bedrooms
3 Bathrooms
14 Sleeps
Wifi
- Details
Description
Fond, family memories will truly be made when you spend your Deep Creek getaway in the charismatic home known as Finn McCool's. This 5 bedroom home boasts a phenomenal lakefront with a private dock, ideal for swimming on hot summer days. After an exciting day of hiking and biking at Swallow Falls State Park, located just minutes away, come back and relax on the large expansive deck. Barbeque and dine outside at the picnic table and then roast s'mores at...
Amenities
Wifi
Additional info
Bedrooms:5
Sleeps:14
Bathrooms:3
Rating Overall Score89%
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Excellent
Lovin' Life Deep Creek - Luxury home w/ lake views
5br Home/Apartment
5 Bedrooms
3 Bathrooms
14 Sleeps
Wifi,
Gym,
Parking
- Details
Description
The Space Location Location Location!!! Welcome to our luxurious vacation log home at Deep Creek Lake! The house has all of the high end features you would want in a home including a whole house security system for your peace of mind. We offer free WiFi throughout. We have thought of everything and have left no stone unturned for you and your family for your Deep Creek Lake and Wisp Resort vacation. If it's in your kitchen, its in our kitchen...
Amenities
Wifi
Gym
Parking
Additional info
Bedrooms:5
Sleeps:14
Bathrooms:3
Rating Overall Score100%
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Excellent
The Original Hob
1br Other
1 Bedroom
1 Bathroom
2 Sleeps
Pets OK,
Parking
- Details
Description
The Space This is perfect for 2 couples! Hob and Molly (separate listing) share the kitchen and bath unit, so coming with another couple or your older children gives you full access to all amenities with friends and family! Of course, it's always fun to meet new people too! Guest Access Guests have access to grounds around the cabins including the hammock and swings, the outdoor fireplace and the creek. Interaction with Guests We are in and around. Guests that arrange for consultations and...
Amenities
Pets OK
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
OWLS NEST, 2 bedroom Cozy Cabin, Lake Waterfront, Private Dock, wHotTub&Linens
2br Cabin
2 Bedrooms
1 Bathroom
4 Sleeps
Gym,
Parking,
Wifi
- Details
Description
RESERVE TODAY - CONTACT OWNER The property is rated exceptional by VRBO and HomeAway. OWLS NEST, DEEP CREEK LAKE, MARYLAND: Using this site (1) Select Dates, then (2) Contact Owner to contact owner. Linens, towels, kayaks, wood, cleaning, and hot tub and basic supplies are included for $75.00. The 12% tax is added. Owls Nest is a perfect romantic getaway for an anniversary or honeymoon or a quiet escape for small family. Welcome to...
Amenities
Gym
Parking
Wifi
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score99%
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Excellent
Glamping - Cozy Hut - Cortina
1br Hut
1 Bedroom
6 Bathrooms
4 Sleeps
Pets OK,
Parking
- Details
Description
The Space 300 acres of private land, with miles of groomed trails and access to the Youghiogheny River. Right next door to Sate Parks and State Forest and just a 10 minute drive from Deep Creek Lake. There are 5 huts available and listed separately. Glamping hut Stanley also has a tipi beside it which you can rent for an additional fee - it's a great space for kids. Please check all listings for availability. It is...
Amenities
Pets OK
Parking
Additional info
Bedrooms:1
Sleeps:4
Bathrooms:6
Rating Overall Score100%
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Good
Beautiful 4 Bedroom Lakefront home with hot tub and private dock!
4br Bedroom
4 Bedrooms
3 Bathrooms
8 Sleeps
Wifi
- Details
Description
El Dorado is a delightful lake cottage with cozy furnishings, warm pine walls, beamed cathedral ceilings and a beautiful stone fireplace. Stunning views of Deep Creek Lake can be seen from almost every room in this charming chalet. Relax in the bubbling hot tub after a day on the lake or fish off your private dock. The family room was recently enhanced with a pool table and foosball table for the game enthusiast. Enjoy the ambiance of the lake area,...
Amenities
Wifi
Additional info
Bedrooms:4
Sleeps:8
Bathrooms:3
Rating Overall Score82%
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Excellent
Molly
1br Other
1 Bedroom
1 Bathroom
2 Sleeps
Pets OK,
Parking
- Details
Description
The Space Molly was designed and built for a line of accessory buildings for Hobbitat. We knew it would be perfect as a guest house! The sound of the creek is wonderful to fall asleep to. This is perfect for 2 couples! The Original Hob (separate listing) is the accompanying cabin. Guest Access In addition to the common area around the cabins, the hammock strung in the shade of a bent tree and the creek, there is an outdoor fireplace and grill behind...
Amenities
Pets OK
Parking
Additional info
Bedrooms:1
Sleeps:2
Bathrooms:1
Rating Overall Score100%
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Excellent
Book 2 nights in Oct get 3rd free! 10 Minutes to WISP Hot Tub Fire Pit boat slip
3br Chalet
3 Bedrooms
2 Bathrooms
8 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Welcome to Deep Retreat Chalet with amenities including lake access, hot tub, fire pit, wifi and hdtv's. Air Conditioning, 2nd floor full bath and 20x30 Paver Patio! W We cater to families as well as small groups that are looking for the ideal cozy getaway. Looking for the perfect spot for your romantic get away? How about for a girls or guys weekend away? Look no further Deep Retreat Chalet has all you need to make lasting memories. (If you...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:2
Rating Overall Score98%
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Excellent
Glamping - Cozy Hut Delta
Hut
6 Bathrooms
4 Sleeps
Smoking,
Pets OK,
Parking
- Details
Description
The Space 300 acres of private land, with miles of groomed trails and access to the Youghiogheny River. Right next door to Sate Parks and State Forest and just a 10 minute drive from Deep Creek Lake. There are 5 huts available and listed separately. Glamping hut Stanley also has a tipi beside it which you can rent for an additional fee - it's a great space for kids. Please check all listings for availability. It is...
Amenities
Smoking
Pets OK
Parking
Additional info
Sleeps:4
Bathrooms:6
Rating Overall Score100%
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Good
Dazzling 3 Bedroom Home w/ Hot tub
3br Bedroom
3 Bedrooms
2 Bathrooms
10 Sleeps
Wifi
- Details
Description
Prepare to be dazzled by the sophistication and grandeur that is Cedar Ridge. This alluring 3 bedroom split level lakefront is the perfect choice for the small family escape or for the couple's retreat. Located on the western end of the lake, the home provides you with a tranquil, serene setting, a fabulous hiking trail that winds around the lake's edge, and a plethora of amenities that will provide hours of entertainment. Your Great Room boasts plush leather seating, a...
Amenities
Wifi
Additional info
Bedrooms:3
Sleeps:10
Bathrooms:2
Rating Overall Score89%
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Excellent
Glamping - Cozy Hut - Stanley
Hut
6 Bathrooms
4 Sleeps
Smoking,
Pets OK,
Parking
- Details
Description
The Space 300 acres of private land, with miles of groomed trails and access to the Youghiogheny River. Right next door to Sate Parks and State Forest and just a 10 minute drive from Deep Creek Lake. There are 5 huts available and listed separately. Glamping hut Stanley also has a tipi beside it which you can rent for an additional fee - it's a great space for kids. Please check all listings for availability. It is...
Amenities
Smoking
Pets OK
Parking
Additional info
Sleeps:4
Bathrooms:6
Rating Overall Score100%
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Good
Incredible Lakefront w/Spacious Deck
5br Other
5 Bedrooms
4 Bathrooms
14 Sleeps
Wifi
- Details
Description
Mountain memories start here! Highland Retreat is a marvelous 5 bedroom lakefront home that combines elegant décor with a bevy of fun amenities. Located on the western end of the lake, you and your guests will love cooling off on hot summer days by swimming and splashing from your very own private dock. Spacious cathedral ceilings, large windows and a spectacular stone fireplace create the perfect warm ambience for gathering in the Great Room. Enjoy a game of billiards in...
Amenities
Wifi
Additional info
Bedrooms:5
Sleeps:14
Bathrooms:4
Rating Overall Score83%
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Excellent
The Owl's Nest at Deep Creek
3br Other
3 Bedrooms
3 Bathrooms
9 Sleeps
Wifi,
Parking
- Details
Description
The Space Brand New mountain home. Sleeps 9, hot tub, screened porch, deck backs up to woods, outdoor fire pit, indoor gas fireplace, well equipped kitchen, coffee maker, crock pot, dish washer, Wi-Fi , cable with 32" flat screen TV and movie channels (Showtime/HBO), plenty of board games, puzzles, & books. The Owl’s Nest is a captivating 3 bedroom home nestled in a quiet community. The tranquil wooded setting provides just enough shade to ensure lots of privacy throughout your stay....
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:9
Bathrooms:3
Rating Overall Score100%
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Excellent
Roomy, lakefront, dog-friendly home w/hot tub, game room, dock and more!
6br Bedroom
6 Bedrooms
7 Bathrooms
25 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
This spacious Oakland home is the perfect choice for your next large family gathering. It accommodates up to 25 guests and offers a high-end yet comfortable home base with amenities like two hot tubs, a game room, a dock with your very own slip, and much more! Come live the good life, and bring along the family dog (for a small nightly fee) to make your vacation truly complete! Ensconced by lush laurel and the beautiful waters of Deep Creek Lake,...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:6
Sleeps:25
Bathrooms:7
Rating Overall Score96%
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Excellent
Historical Lakin Victorian mountaintop Retreat
7br Retreat
7 Bedrooms
4 Bathrooms
14 Sleeps
Wifi,
Gym,
Parking
- Details
Description
The Space The space is large and has room for everybody. Full basement has a exercise room, laundry, and access to the back yard, First floor: dining room, living room, Foyer with guest information, Half Bathroom, 2 Mudrooms, Access Fire door to basement, large kitchen with table for 8 and Stainless Steel modern appliances, 2nd Floor: 2 Full bathrooms, 1 half-bath, 3 bedrooms, 1 TV room/Sofabed (former 4th bedroom), 3rd Floor: Sitting room and 3 additional bedrooms. Large back yard with...
Amenities
Wifi
Gym
Parking
Additional info
Bedrooms:7
Sleeps:14
Bathrooms:4
Rating Overall Score100%
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Excellent
Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!
3br Other
3 Bedrooms
2 Bathrooms
8 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Welcome to a truly special lakefront experience on the shores of Deep Creek Lake. Located in a private community on a peninsula at the Northern end of the lake, our home offers peaceful relaxation far away from busy roads and traffic. Families with children or pets will especially appreciate the one lane road cul de sac location with no through traffic. The property features almost 100 feet of western exposure lakefront in a quiet cove with a...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:2
Rating Overall Score98%
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Good
Adorable Chalet in peaceful setting with multiple game tables!
4br Chalet
4 Bedrooms
2 Bathrooms
10 Sleeps
Wifi
- Details
Description
Home Sweet Cabin is a charismatic mountain home that rests in a quiet, peaceful cove. Expansive wooden cathedral ceilings highlight the stone fireplace and gives promises of nights spent bonding with family and friends. The open floor plan allows you to entertain your guests while preparing the ultimate feast in the well-stocked kitchen. Your main level houses two of your bedrooms, one with a Queen sized bed and the other with a Twin and Double sized bed. Luxury linens and...
Amenities
Wifi
Additional info
Bedrooms:4
Sleeps:10
Bathrooms:2
Rating Overall Score87%
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Excellent
Lake View Chalet in Alpine Lake Resort
3br Chalet
3 Bedrooms
3 Bathrooms
8 Sleeps
Gym,
Parking,
Pets OK,
Wifi
- Details
Description
Come visit the beautiful Alpine Lake and stay at our cabin Lakefront This chalet-style home is located in a community where you can enjoy: swimming, boat ride, beach, a picnic pavilion, a 18-hole golf course, tennis court, cross country skiing and fishing right in front of Lakefront All these facilities can be enjoyed by you. Wisp Ski resort is only 30-40 minutes away! With wildlife, a beautiful scenery and rooms for your family, nothing can go wrong by choosing Lakefront. This house is located in one...
Amenities
Gym
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score98%
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Excellent
Red Run Cabin
3br Cabin
3 Bedrooms
2 Bathrooms
Pets OK
- Details
Description
Red Run Cabin is a 1 story 3 bedroom cottage with a finished basement on an acre wooded lot near the west end of Deep Creek Lake, accomodating up to 6 people. It has lake access through the Red Run Restaurant property leading to a sandy beach and shallow lake bottom far out into the lake, making it ideal for small children. There is no dock for this property, but it is located in a park-like setting. ...
Amenities
Pets OK
Additional info
Bedrooms:3
Bathrooms:2
Rating Overall Score100%
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Excellent
Bear Crossing @ Yough Mt. Resort
3br Resort
3 Bedrooms
2 Bathrooms
10 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space Bear Crossing is ideal for folks looking to just get away from the world for a bit! The setting is about as private as you could imagine with no artificial lights at night and only the sounds of nature! Quiet and secluded? You got it! BTW - Bear Crossing has an AWESOME firepit - likely the best you will ever see! Plan on relaxing with some beverages and gazing at the stars at least 1 night to complete your Appalachian...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:3
Sleeps:10
Bathrooms:2
Rating Overall Score100%
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Excellent
Gorgeous Lake Front Resort Home in the Mountains
4br Resort
4 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
'The Highlander' was lovingly built by Jeanne Casale Bourn, who decorated it with beautiful quilts and other local treasures. Her touch is still evident – comfortable, modern and absolutely relaxing. The house looks directly onto the middle of the lake with a view from the beach to the lodge. A wrap around deck (partially enclosed) provides a wonderful view. The Highlander boasts 11 rooms, 3 bath, 4 bedrooms (sleeps 8: bed - 1 queen; 2...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:4
Sleeps:8
Bathrooms:3
Rating Overall Score91%
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Excellent
Dock Holiday-Lake access with a boat slip
3br Boat
3 Bedrooms
3 Bathrooms
8 Sleeps
Wifi,
Parking
- Details
Description
The Space First step: Relax ( stay connected with Wi-Fi). We've made it easy to put things down--the spacious mudroom provides a bench, shelves and racks for your skis and snowboards, plus room for helmets, hats and scarves. You'll find the new kitchen, open to the light and airy living room that offers plenty of plush seating and a pull-out couch, 50-inch flat screen TV and game table. The screened-in porch is well lit for family gatherings or quiet reading. Make yourself comfortable...
Amenities
Wifi
Parking
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score100%
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Excellent
Glamping - Cozy Hut - Ardennen
Hut
6 Bathrooms
4 Sleeps
Smoking,
Pets OK,
Parking
- Details
Description
The Space 300 acres of private land, with miles of groomed trails and access to the Youghiogheny River. Right next door to Sate Parks and State Forest and just a 10 minute drive from Deep Creek Lake. There are 5 huts available and listed separately. Glamping hut Stanley also has a tipi beside it which you can rent for an additional fee - it's a great space for kids. Please check all listings for availability. It is...
Amenities
Smoking
Pets OK
Parking
Additional info
Sleeps:4
Bathrooms:6
Rating Overall Score100%
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Good
Boondock Mabuhay Getaway
3br Other
3 Bedrooms
2 Bathrooms
6 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space 3 level townhome with wifi. Approximately 900sq ft, enough for a small family. Main bedroom on the 2nd floor. Walkout first floor level has a double deck bed, with a small private bathroom, shower, and stackable washer and dryer. 2nd floor has the main living room, kitchen, dinette, and main bedroom with full size bed. Netflix, Hulu, Amazon Prime, etc available through ROKU. Portable AC in the main bedroom. Main bathroom with tub on the second floor....
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:2
Rating Overall Score90%
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Excellent
FIVE STAR REVIEWS! Enjoy the bold colors of FALL! Book Ski weekends!
4br Chalet
4 Bedrooms
4 Bathrooms
10 Sleeps
Parking,
Wifi
- Details
Description
A short walk to the lake to enjoy deep water, dock and fishing! As you enter Timroc II a rustic feel encompasses you. With it's simple decor and all modern conveniences, the setting is quiet, serene and is surrounded by 2 acres of nature. Four comfortable sized bedrooms, each with large windows letting in natural daylight. First floor master with it's custom tiled oversized shower, hardwood flooring throughout, many sliders for easy access to screened...
Amenities
Parking
Wifi
Additional info
Bedrooms:4
Sleeps:10
Bathrooms:4
Rating Overall Score98%
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Excellent
Spacious 4 bedroom home with phenomenal lakefront!
4br Bedroom
4 Bedrooms
4 Bathrooms
10 Sleeps
Wifi
- Details
Description
For the chance to stay in one of Deep Creek's most desired vacation homes, book a relaxing escape at Stargazer where peaceful days and starry nights are guaranteed. Mesmerizing from the second that you step inside, prepare to be swept away by the extraordinary lake views that greet you from the large expansive windows. Elegant furnishings, glistening dark hardwood floors, and vaulted cathedral ceilings give the Great Room a majestic feel while the double sided fireplace ensures comfort and warmth...
Amenities
Wifi
Additional info
Bedrooms:4
Sleeps:10
Bathrooms:4
Rating Overall Score94%
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Excellent
Raccoon Retreat @ Yough Mountain Resort
2br Retreat
2 Bedrooms
1 Bathroom
6 Sleeps
Pets OK,
Parking
- Details
Description
Interaction with Guests We have nearby Offlake Rentals serving as our local property manager to ensure that every issue is promptly and professionally handled. We are generally available Via AirBnB messaging but the rental office is staffed 7 days a week. The Neighborhood Very good question as Deep Creek Lake is one of the wonderful outdoor attractions that Garrett County has to offer (certainly many other attractions are primed for your exploration as well... Maryland's Tallest Mountain, Highest free-falling water fall, largest State...
Amenities
Pets OK
Parking
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:1
Rating Overall Score100%
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Good
2 bedroom in historic Oakland, walk to everything!
2br Bedroom
2 Bedrooms
1 Bathroom
4 Sleeps
Wifi,
Parking
- Details
Description
The Space Large and charming 2-bedroom, 1 jack and Jill bathroom, with large walk in closet. Great for a long ski weekend or an anytime getaway. Very cozy and peaceful setting. Bedroom 1 has a Queen Bed and large windows, and electric fireplace, bedroom 2 has a queen bed and two nightstands with drawers. Living room has a new large sofa with ottoman. Apartment is located in a former Large Victorian Home that served as a Vacation home for a...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:4
Bathrooms:1
Rating Overall Score90%
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Good
The Homestead
3br Home/Apartment
3 Bedrooms
3 Bathrooms
6 Sleeps
Parking
- Details
Description
The Space The 2,000 sq. ft. house features the master bedroom and two smaller bedrooms on the upper level with the living room, dining area, and kitchen downstairs. As our family wanted a more "open" design, there is no door to the master bedroom. The living room features a day bed that serves as a couch and as two beds - there is a pull out trundle underneath. Each room has a closet and dresser with ample space. The three bathrooms all...
Amenities
Parking
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:3
Rating Overall Score90%
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Checking availability...
Excellent
Deep Camp @ Deep Creek - Lake Views
2br Other
2 Bedrooms
2 Bathrooms
6 Sleeps
Wifi,
Parking
- Details
Description
The Space Cozy camp at the end of a dead end road. Secluded but minutes from all lake amenities, skiing at Wisp resort, restaurants, and entertainment. Walking trails abound. Guest Access Entire camp/property. The Neighborhood Wooded neighborhood. Secluded. Getting Around Parking for 3 cars. Other Things to Note No pets allowed! Fishing poles are available. The hot tub is NOT available to guest. There a security camera in the the front and back that face outside . Please do not touch. Turn on the hot water and pump circuit breakers outside when you...
Amenities
Wifi
Parking
Additional info
Bedrooms:2
Sleeps:6
Bathrooms:2
Rating Overall Score100%
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Checking availability...
Excellent
Big Rock Candy Mountain Lodge - Deep Creek Lake
5br Hotel
5 Bedrooms
4 Bathrooms
14 Sleeps
Wifi,
Parking
- Details
Description
The Space Relax in the great room with surround sound and watch a movie from our DVD library , exercise with a game on the Wii, play pool or air-hockey in the basement, or check up on email on our high-speed wireless network. Enjoy all the modern amenities this vacation home has to offer - or take a 5 minute walk to dip your toes in the lake, relax on the partially-covered wraparound deck with a book and enjoy the filtered lake...
Amenities
Wifi
Parking
Additional info
Bedrooms:5
Sleeps:14
Bathrooms:4
Rating Overall Score100%
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Checking availability...
Excellent
Centrally located Craftsman home close to DCL state park!
4br Home/Apartment
4 Bedrooms
3 Bathrooms
12 Sleeps
Wifi
- Details
Description
Explore, relax and take a well-deserved break at Deep Breath! Convenient to area activities and attractions, it is the perfect home base for your Deep Creek Lake vacation. The spacious interior of this Craftsman-style home is brimming with attention to detail. Upon entering, a dual sided gas fireplace will immediately catch your eye. It is easy to imagine fireside dinners at the dining table that comfortably seats eight. Bring a good book and enjoy the firelight from the cozy window...
Amenities
Wifi
Additional info
Bedrooms:4
Sleeps:12
Bathrooms:3
Rating Overall Score96%
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Excellent
7 min walk to the lake! Cozy Yellow Stone Cabin hot tub, fireplaces, wifi, hdtv
3br Cabin
3 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Looking for the perfect getaway? Look no further than Deep Retreat Cabin! Located in the highly sought after Yellow Stone Village, Deep Retreat is comfortable, cozy and has everything you need for your time away. With new ownership/management and lots of updates you are sure to enjoy your stay Deep Retreat offers- 3 Bed 3 Bath with a full size sleep Sofa (3 Queen Beds Sleeps 8 Comfortably) 2 Fire Places - 2 Easy Light Fire Logs and Fire Wood are included...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score100%
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Checking availability...
Excellent
Sunny Escape - Lakefront 3 Bedroom Home With Dock. Easy Access To Amenities.
3br Bedroom
3 Bedrooms
2 Bathrooms
8 Sleeps
Gym,
Parking,
Pets OK,
Wifi
- Details
Description
This is a family vacation home that was an original Deep Creek stone fishing cabin. It has been updated with modern fixtures, air conditioning, cable HDTV with HBO, and internet access. Original cypress paneling and trim intact. Hardwood floors throughout and large Great Room for family gatherings. Beautiful views of the lake and surrounding forest in a quiet but central location. Up to two well behaved dogs allowed if you check the pet fee box....
Amenities
Gym
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:2
Rating Overall Score97%
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Excellent
Deep Creek Lake, Cozy Lake Cottage
3br Cottage
3 Bedrooms
1 Bathroom
6 Sleeps
Wifi,
Pets OK,
Parking
- Details
Description
The Space The space is cozy, with a fully equipped kitchen and beautiful outdoor areas. Our guests have access to our canoe and kayaks, life jackets, board games, sleds and firewood. It is a wonderful place to make memories with family and friends. Guest Access You will be able to access all areas of the house and yard. This is a private home and you have full use of the space that is available. Interaction with Guests My guests will receive access...
Amenities
Wifi
Pets OK
Parking
Additional info
Bedrooms:3
Sleeps:6
Bathrooms:1
Rating Overall Score100%
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Checking availability...
Excellent
Lovin Life Deep Creek 5 STAR -5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub
5br Bedroom
5 Bedrooms
3 Bathrooms
14 Sleeps
Gym,
Parking,
Wifi
- Details
Description
Location Location Location!!! Welcome to our luxurious vacation log home at Deep Creek Lake! The house has all of the high end features you would want in a home including a whole house security system for your peace of mind. We offer free WiFi throughout. We have thought of everything and have left no stone unturned for you and your family for your Deep Creek Lake and Wisp Resort vacation. If it's in your kitchen, its in our kitchen too...including...
Amenities
Gym
Parking
Wifi
Additional info
Bedrooms:5
Sleeps:14
Bathrooms:3
Rating Overall Score98%
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Checking availability...
Excellent
Family- and dog-friendly home w/ deck, forest view - close to lake & ski slopes
3br Home/Apartment
3 Bedrooms
3 Bathrooms
8 Sleeps
Parking,
Pets OK,
Wifi
- Details
Description
Enjoy your next family vacation near the shore of beautiful Deep Creek Lake at this dog-friendly, well-appointed home in the woods complete with a furnished deck, a gas grill, and plenty of space for up to eight guests. This home is conveniently close to Garrett Highway for easy access to nearby communities like Oakland to the south and McHenry to the north. Spend your summers on (or in) Deep Creek Lake where you can swim, boat, and fish for bass, trout,...
Amenities
Parking
Pets OK
Wifi
Additional info
Bedrooms:3
Sleeps:8
Bathrooms:3
Rating Overall Score96%

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Vacation Rentals in Oakland

Choose the perfect accommodation for your trip at AllTheRooms.com. We aggregate Airbnb, VRBO, Glamping Hub and more. Oakland has 1055 hotels, vacation rentals and other unique places to stay, with prices to suit budget travelers, luxury travelers and everything in between. A trip to Oakland can be affordable - our lowest price accommodation is available at $null per night. On average, a place to stay in Oakland will cost you $338 per night.

If you need an internet connection during your stay in Oakland, then you can choose from over 345 places to stay that provide WiFi internet. 3 places to stay include a breakfast. Choose from 8 places to stay that provide gym facilities, so you won't miss a single workout. If you are driving to Oakland, you'll want to pick from 301 places to stay that provide parking. We have 14 places to stay that have a pool or jacuzzi.

If you're traveling with a furry friend, then be sure to choose one of the 100 pet-friendly accommodations available.

In Oakland AllTheRooms currently aggregates hotels, vacation rentals, hostels from more than 6 providers, including 222 places to stay from Airbnb, 16 accommodations from VRBO and 16 places to stay from Glamping Hub.

376 accommodations in Oakland have been reviewed: 38% are rated excellent or good. You can instantly book any of 552 places to stay right now.

The Best Oakland Vacation Rentals (Maryland) in October 2018

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