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Search results; Over 1,000 homes in Sheffield

Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 private bathrooms
13–18 Sept
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4.92 out of 5 average rating, 192 reviews
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds, 3 bathrooms
7–12 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
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
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, 69 reviews
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
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
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
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, 96 reviews
Top guest favourite
Home in Sheffield
Great Berkshire Getaway !
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.95 out of 5 average rating, 115 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
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
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 411 reviews
Guest favourite
Flat in Great Barrington
King Bed|2m Ski Resort|Stylish|Fast Wi-Fi
1 king bed, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 91 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 95 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
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
2 single beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 55 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
23–28 Aug
4.91 out of 5 average rating, 171 reviews