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Vacation rentals in Sheffield

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Top-rated vacation rentals in Sheffield

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Loft in Great Barrington

4.99 out of 5 average rating, 317 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

Rental unit in Copake Falls

4.92 out of 5 average rating, 300 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Cottage in Great Barrington

4.93 out of 5 average rating, 266 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Cottage in Sheffield, The Berkshires

4.93 out of 5 average rating, 134 reviews

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

Rental unit in Canaan

4.98 out of 5 average rating, 127 reviews

West Main

1890s home situated on the outskirts of town, entire second floor apartment. The apartment is bright and sunny and super comfortable with 2 bedrooms both with queen beds, 1 bathroom, eat in country kitchen fully equipped.There is a spacious living room with a smart Roku TV, (not cable ) WiFi and access to a private garden space, private entrance and off street parking. Walk to town brewery, pizza and more. Great place to relax after a day of exploring Litchfield county and the Berkshires.

Rental unit in Sheffield

5 out of 5 average rating, 344 reviews

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Guest suite in Canaan

4.98 out of 5 average rating, 328 reviews

Walk to Brewery in Historic Railroad Depot

This light-filled space is in a separate wing of my house with its own private entrance. There is one bedroom with a king-sized bed, spacious living room with table for meals, a large TV, a refrigerator/freezer stocked with bottled water and 1/2&1/2 for coffee, microwave and coffee maker with coffee pods are provided. You will hear the train as it travels through town. There are several places to eat nearby. Be sure to check out GUIDEBOOK on my listing to see what our area offers!!!

Home in Sheffield

4.9 out of 5 average rating, 113 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Rental #1 has 2 bedrooms, a FULLY EQUIPPED KITCHEN and it is SUPERCLEAN! (ALSO SEE THE 1 BEDROOM LISTING #2!) Fully renovated, large garden, private entrance, terrace and parking space. Two Queen size beds. High Speed WiFi. Berkshire Blend coffee/decaf, teas, milk, sugar and juice are a first morning welcome gift. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Home in Great Barrington

4.97 out of 5 average rating, 241 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Rental unit in Sheffield

4.92 out of 5 average rating, 139 reviews

Private Berkshire Barn Apartment

A private entrance and apartment all to yourself. You are within a 2 minute drive of downtown Sheffield or a 10-15 minute walk. Also within a short drive of superb restaurants and local ski areas, Great Barrington, Tanglewood, Jacobs Pillow, The Rockwell Museum and numerous other Berkshire attractions. Also within a short drive of Berkshire, Salisbury, Hotchkiss and Simon's Rock schools.

Home in Sheffield

4.92 out of 5 average rating, 120 reviews

A Private Peninsula Retreat In The Berkshires!

THIS IS MY DREAM COME TRUE!!! I finally found the most perfect lake house in the Berkshires! It is a 2 acre private peninsula jutting out into Mill Pond! Come kayak, stand up paddle, canoe, fish on the pond & hang out on the dock and the deck! 3 bedrooms & 2 full baths- can sleep up to 9. Enjoy music, theater, dance, hiking, museums, skiing, dining, relaxing in the Berkshires!

Vacation home in Great Barrington

4.95 out of 5 average rating, 189 reviews

Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy sunset views with friends and family, before you walk into town for a night out! 10 minutes (2 miles) to Butternut Ski Area This brand new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple.

Vacation rentals for every style

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Unique stays

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Popular amenities for Sheffield vacation rentals

Free parking on premises

Air conditioning

Stay near Sheffield's top sights

Old Mill73 locals recommend

The Barn50 locals recommend

Bartholomew's Cobble Reservation45 locals recommend

Berkshire Mountain Distillers34 locals recommend

Big Elm Brewing31 locals recommend

The Stagecoach Tavern26 locals recommend

Other great vacation rentals in Sheffield

Cabin in Sheffield

5 out of 5 average rating, 21 reviews

Berkshires Cabin with Stunning Views

Barn in Great Barrington

4.95 out of 5 average rating, 81 reviews

Serene Renovated Barn w/ Firepit

Bungalow in Egremont

4.99 out of 5 average rating, 83 reviews

3-bedroom Berkshire bungalow on 2.5 peaceful acres

Home in Sheffield

4.94 out of 5 average rating, 17 reviews

Bull Hill Bungalow

Home in Egremont

5 out of 5 average rating, 16 reviews

The Catamount Haus w. Pool/Hot Tub

Home in Egremont

4.93 out of 5 average rating, 72 reviews

Modern and Stylish Country Lakeside Cottage

Home in Salisbury

5 out of 5 average rating, 43 reviews

Greystone at Twin Lakes

Guesthouse in Sharon

4.99 out of 5 average rating, 95 reviews

Cottage with a Waterfall View

Quick stats about vacation rentals in Sheffield

Total rentals
90 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
4.2K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
50 properties have a dedicated workspace

Frequently Asked Questions

Are there pet-friendly vacation rentals in Sheffield?
Four-legged friends are welcome in Sheffield. Choose from more than 40 vacation rentals for guests traveling with pets.
Do house rentals in Sheffield have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Sheffield. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Sheffield?
Experience the best of Sheffield with our house rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Sheffield have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Sheffield. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Sheffield?
Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with free parking, over 50 homes with a kitchen, over 40 homes with air conditioning, over 50 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Sheffield?
Sheffield has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there vacation rentals with a dedicated workspace in Sheffield?
Yes! Work meets play with ease at over 50 vacation rentals in Sheffield featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Sheffield have wifi?
Absolutely! We offer over 50 house rentals with wifi in Sheffield. Enjoy a tailored experience with all the comforts you desire.

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