Sheffield Vacation Rentals

Our Favorite Vacation Rentals in Sheffield

  • The Old Inn On The Green
    Good11br 4-star Home/Apartment
    Booking.com
    From
    $260
  • Charming Private Guest Suite in Historic Village in the Berkshires
     -1br Studio
    HolidayLettings
    From
    $136
  • 'The Mill River Cabin’ w/ Fireplace & River View!
     2br Cottage
    HolidayLettings
    From
    $417
  • Waterfront Cottage - 10 Mins to Great Barrington!
    Excellent2br Cottage
    HolidayLettings
    From
    $346
  • Zen Cottage in the Woods
     3br Home/Apartment
    HolidayLettings
    From
    $349
  • RiverSong Suite In The Berkshires
    ExcellentHome/Apartment
    HolidayLettings
    From
    $256
  • Beautiful Cottage at the foot of the Berkshires
     2br Cottage
    HolidayLettings
    From
    $272
  • The Smith Farm Homestead
    ExcellentHome/Apartment
    HolidayLettings
    From
    $175

Check prices for these upcoming dates

Sheffield Vacation Rentals with a Pool

  • Race Mountain House
    Excellent4br Home/Apartment
    Airbnb
    From
    $591
  • Treetops: Indoor pool & only 10 min to Catamount!!
    Excellent5br Home/Apartment
    Airbnb
    From
    $1,158
  • Clayton Farm: Sparkling and Bucolic w/ Heated Pool
    Excellent4br Home/Apartment
    Airbnb
    From
    $989
  • Country Castle with indoor pool and MORE, sleeps 12+
     5br Home/Apartment
    Airbnb
    From
    $1,271

Sheffield Vacation Rentals with Wi-Fi

  • The Bungalow in Sheffield MA (The Berkshires)
    Excellent2br Home/Apartment
    Airbnb
    From
    $164
  • Nature lover's delight! Fall Foliage&then Skiing!
    Excellent2br Home/Apartment
    Airbnb
    From
    $110
  • Private Berkshire Barn Apartment
    ExcellentHome/Apartment
    Airbnb
    From
    $123
  • “Elterwater”—the house on the lake
    Excellent2br Home/Apartment
    Airbnb
    From
    $254

Sheffield Pet-Friendly Vacation Rentals

  • Lakefront Berkshires Ski/Summer House, Great Views
    Nice4br Home/Apartment
    HolidayLettings
    From
    $333
  • NEW! Monterey Home w/Porch by Beach & State Parks!
     3br Home/Apartment
    HolidayLettings
    From
    $405
  • Best Vacation Home in Berkshires..(Winter & rest of seasons 1, 2, or 3 families)
     6br Home/Apartment
    HolidayLettings
    From
    $998
  • Cozy Stockbridge Home - Walk To Golf Course!
     2br Home/Apartment
    HolidayLettings
    From
    $401

Sheffield Travel Guide

Found in the Housatonic River Valley is the charming town of Sheffield. This New England town in Massachusetts attracts more visitors every year because of its historical sites, as well as outdoor recreation. Of course, who can forget, UFOs too as the town is home to the UFO Monument Park. When it comes to shopping in Sheffield, visitors can enjoy local shops and antique stores. Dining is also kept local, with everything from casual cafes and home cooking to upscale and elegant dining restaurants.

Things to Do in Sheffield

To catch a glimpse into the local colonial life, visit the Colonel John Ashley House. To stretch your legs on a long hike, head to Bartholomew’s Cobble and reconnect with nature. There is tons of local wildlife to learn about, as well as beautiful views of the Housatonic on some of the trails. Race Brook Falls is also a popular hike with rewarding views and spectacular scenery. To see the first UFO incident in the country, head to Thom Reed UFO Memorial Park. It is believed that a UFO was seen in 1969 and that Reeds saw a vessel in the sky. Visitors can wander around the park and learn more about our planet's visitors.

Best Time to Visit Sheffield

The best time to enjoy outdoor recreation in Sheffield is during the summer months.

Price and Availability in Sheffield

Most expensive
Most availability
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The cheapest day to stay at a vacation rental in Sheffield tends to be Wednesday, while the most expensive day tends to be Friday. Vacation homes in Sheffield tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Sheffield is in December, while the cheapest month is in March. The most popular time to book a vacation rental in Sheffield is in the high season in August. Sheffield has its low season in April, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Sheffield

Rainy days
54° -11°
5
60° -5°
3
67°
1
74° 19°
5
83° 36°
4
85° 39°
5
90° 51°
4
86° 43°
2
85° 34°
3
73° 29°
8
66° 11°
4
53°
5
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Sheffield. The hottest month in Sheffield is June, when temperatures peak at 90 ˚F. The coolest month is December, when temperatures drop to -11 ˚F. The wettest month in Sheffield is March with 8.3 inches of rain, while the driest month is October with 1.25 inches of rain.

What Expert Travelers Think

  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

    Jaz
    JazThe Life of a Social Butterfly
  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston

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