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Search results; Over 1,000 homes in Sheffield

Top guest favourite
Cabin in Sheffield
The Berkshires Cabin with Stunning Views
4 bedrooms, 6 beds, 2 private bathrooms
4–9 Oct
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4.97 out of 5 average rating, 60 reviews
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
New place to stay
Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 bathrooms
8–13 Sept
New place to stay
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
27 Aug – 1 Sept
4.78 out of 5 average rating, 101 reviews
Superhost
Home in Sheffield
New: Heated Pool, SIP, 1 Level Living: Sleeps 10!
3 bedrooms, 7 beds, 3 bathrooms
7–12 Sept
New place to stay
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
23–28 Aug
4.77 out of 5 average rating, 349 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 71 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 97 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 28 reviews
Flat in Egremont
Berkshires Charm Private Apartment
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
New place to stay
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.82 out of 5 average rating, 34 reviews
Home in Sheffield
Large, light, and airy
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Oct
4.75 out of 5 average rating, 16 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio
1 king bed, 1 bathroom
23–28 Aug
4.83 out of 5 average rating, 112 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
24–29 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 192 reviews
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 bathrooms
25–30 Sept
4.9 out of 5 average rating, 99 reviews