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Search results; Over 1,000 homes in Sheffield

Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
1 bedroom, 1 bed, 1 private bathroom
17–22 Sept
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4.98 out of 5 average rating, 58 reviews
Guest favourite
Home in Sheffield
Serene Berkshire Artist's House
3 bedrooms, 3 beds
14–19 Sept
4.99 out of 5 average rating, 69 reviews
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds
14–19 Sept
New place to stay
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed
4–9 Nov
4.93 out of 5 average rating, 184 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds
28 Sept – 3 Oct
4.78 out of 5 average rating, 101 reviews
Top guest favourite
Home in New Marlborough
Grand View
4 bedrooms, 5 beds
16–21 Sept
4.98 out of 5 average rating, 57 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
20–25 Sept
4.92 out of 5 average rating, 193 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds
17–22 Sept
4.78 out of 5 average rating, 352 reviews
Top guest favourite
Home in Sheffield
House Among Trees - A Perfect Holiday Getaway
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 98 reviews
Guest favourite
Home in Sheffield
Private Berkshires Estate w/ Tennis Court
4 bedrooms, 5 beds
26–31 Oct
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds
14–19 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds
15–20 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 30 reviews
Top guest favourite
Home in Great Barrington
Berkshires Black Abbey
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 46 reviews
Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds
14–19 Sept
New place to stay
Guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds
12–17 Oct
4.9 out of 5 average rating, 101 reviews
Top guest favourite
Home in Great Barrington
The Hideaway: Berkshire Home - village of Egremont
3 bedrooms, 7 beds
14–19 Sept
4.95 out of 5 average rating, 148 reviews
Top guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds
21–26 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
22–27 Sept
4.98 out of 5 average rating, 55 reviews