A covered wooden structure with a sloped roof, surrounded by greenery and trees.

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Sheffield vacation homes

An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

1. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥39,261
￥82,561 total
includes taxes & fees
Sep 22 - Sep 23
Cheerful 3-bedroom cottage with woodstove
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

2. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥42,917
￥64,982 total
includes taxes & fees
Aug 29 - Aug 30
Home in Great Barrington
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

3. Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is ￥30,399
￥47,273 total
includes taxes & fees
Sep 21 - Sep 22
Cozy Riverside Berkshires Retreat
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

4. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is ￥50,669
￥88,559 total
includes taxes & fees
Sep 1 - Sep 2
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

5. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is ￥27,816
￥50,601 total
includes taxes & fees
Sep 1 - Sep 2
Sweet Cozy Victorian in Housatonic. Close to everything.
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

6. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥44,824
￥92,573 total
includes taxes & fees
Sep 21 - Sep 22
Treetop Hideaway in Tyringham
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

7. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ￥8,424
￥45,985 total
includes taxes & fees
Sep 13 - Sep 14
Real Estate: Therapy - Lake, Laundry, Love it
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

8. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (7 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ￥90,411
￥211,424 total
includes taxes & fees
Aug 23 - Aug 24
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

9. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is ￥64,176
￥107,660 total
includes taxes & fees
Aug 23 - Aug 24
Fantastic 2-bedroom house with AC in quaint Hillsdale.
A modern kitchen with a central island, bar stools, a stove, and a sink.

10. Renovated Downtown Great Barrington House

Renovated Downtown Great Barrington House
Great Barrington
8.0 out of 10, Very Good, (2 reviews)
"This is a very nice place to stay. My wife and I both remarked on how comfortable we felt there. A proper home away from home. It was well stocked on all fronts, including the kitchen. And I think what put the finishing touch on was the attention to detail... The towels were large, the bathroom rolls were Charmin Ultrasoft, and there were tissue boxes everywhere you're likely to need them. The hosts seem to work with a service, so you can reach someone with questions immediately, and the hosts...
United States
Anonymous traveler
The price is ￥142,674
￥243,037 total
includes taxes & fees
Aug 23 - Aug 24
Renovated Downtown Great Barrington House
A living room with a brown leather sofa, two grey armchairs, a glass coffee table, and a wooden side table with a lamp.

11. stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
9.0 out of 10, Wonderful, (4 reviews)
"Property was just as described, clean and well equipped. Had excellent communication with the host. Would highly recommend staying here."
United States
Donna K.
The price is ￥25,750
￥61,253 total
includes taxes & fees
Sep 20 - Sep 21
stylish Berkshires Retreat
A hot tub with a string of lights above it, set against a dark night sky.

12. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,464
￥63,065 total
includes taxes & fees
Aug 25 - Aug 26
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A loft bedroom with a television, wooden shelves, a ladder, and a skylight.

13. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
The price is ￥19,743
￥35,819 total
includes taxes & fees
Aug 30 - Aug 31
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

14. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (7 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥26,228
￥63,922 total
includes taxes & fees
Sep 9 - Sep 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

15. Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
Mtn-View Retreat in Huson Valley: Great for Groups
An outdoor deck with a grill, seating area, and a view of the surrounding greenery.

16. Stockbridge In-town Escape

Stockbridge In-town Escape
Stockbridge
The price is ￥63,981
￥101,008 total
includes taxes & fees
Aug 30 - Aug 31
Stockbridge In-town Escape
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

17. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
The price is ￥80,831
￥138,762 total
includes taxes & fees
Sep 2 - Sep 3
Stylish Mid-century Modern Berkshires Cape
A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

18. NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is ￥43,539
￥125,442 total
includes taxes & fees
Aug 24 - Aug 25
NEW: Chic Modern Barn Style Home in Fun Area
A camping setup with a metal chair and a table by a river in a forest.

19. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (11 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is ￥31,790
￥54,653 total
includes taxes & fees
Sep 20 - Sep 21
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A rustic interior with wooden beams, multiple windows, and a kitchen area with dishes and a coffee maker.

20. rural, serene + sophisticated space

rural, serene + sophisticated space
Red Hook
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful property with unique accommodations in the Hudson Valley"
United States
BRIAN PATRICK M.
The price is ￥47,529
￥59,820 total
includes taxes & fees
Aug 30 - Aug 31
rural, serene + sophisticated space
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheffield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"We always stay here on our trips to and from Maine and New York, we love it. So appreciate the kind staff and the pool. Great and we’ll see you next time!"
Rebecca 1-night trip
Posted 7 hours ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Sheffield

Sheffield Vacation Homes information

Number of reviews
8,001
Accommodation
421 Vacation Homes
Lowest Price
￥12,015
Highest Price
￥62,761