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Search results; Over 1,000 homes in Sheffield

Top Guest favourite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 private bath
26 Sept – 1 Oct
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5.0 out of 5 average rating, 409 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 baths
7–12 Sept
4.98 out of 5 average rating, 54 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 baths
15–20 Aug
4.78 out of 5 average rating, 101 reviews
Top Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bath
27 Aug – 1 Sept
4.99 out of 5 average rating, 68 reviews
Top Guest favourite
Apartment in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bath
15–20 Oct
4.93 out of 5 average rating, 180 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 baths
23–28 Aug
5.0 out of 5 average rating, 9 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 baths
23–28 Aug
4.77 out of 5 average rating, 347 reviews
Top Guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 baths
9–14 Aug
4.9 out of 5 average rating, 99 reviews
Top Guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 baths
23–28 Aug
5.0 out of 5 average rating, 96 reviews
Superhost
Guesthouse in Sheffield
The Cottage at 3 Sisters Farm
2 bedrooms, 2 queen beds, 2 baths
8–13 Sept
4.77 out of 5 average rating, 13 reviews
Top Guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed, 1 bath
23–28 Aug
5.0 out of 5 average rating, 95 reviews
Guest favourite
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom, 1 bath
9–14 Sept
4.85 out of 5 average rating, 46 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 baths
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds, 2.5 baths
31 Aug – 5 Sept
4.82 out of 5 average rating, 34 reviews
Top Guest favourite
Room in Sheffield
Beautiful Room in Hartfield House - The Berkshires
2 beds, 1 bath
9–14 Sept
4.97 out of 5 average rating, 37 reviews
Top Guest favourite
Home in Sheffield
Great Berkshire Getaway !
1 bedroom, 1 queen bed, 1 bath
4–9 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 baths
16–21 Aug
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 baths
16–21 Aug
5.0 out of 5 average rating, 7 reviews
Top Guest favourite
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
1 bedroom, 1 queen bed, 1 bath
26–31 Oct
4.95 out of 5 average rating, 421 reviews
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