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Search results; Over 1,000 homes in Sheffield

Top guest favourite
Room in Sheffield
Beautiful Room in Hartfield House - The Berkshires
1 bedroom, 2 beds, 1 private bathroom
9–14 Sept
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4.97 out of 5 average rating, 37 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
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
27 Aug – 1 Sept
4.78 out of 5 average rating, 101 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds
23–28 Aug
4.77 out of 5 average rating, 348 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
27 Aug – 1 Sept
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds
23–28 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds
21–26 Sept
5.0 out of 5 average rating, 96 reviews
Guest favourite
Guest house in Sheffield
Dandelion Hill Farm Cottage
1 bedroom, 1 bed
16–21 Aug
4.85 out of 5 average rating, 26 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds
16–21 Aug
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds
26 Sept – 1 Oct
5.0 out of 5 average rating, 410 reviews
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds
17–22 Aug
4.9 out of 5 average rating, 99 reviews
Home in Sheffield
Large, light, and airy
3 bedrooms, 3 beds
9–14 Oct
4.75 out of 5 average rating, 16 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed
23–28 Aug
5.0 out of 5 average rating, 95 reviews
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds
31 Aug – 5 Sept
4.82 out of 5 average rating, 34 reviews
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
2 single beds
23–28 Aug
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds
16–21 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Sheffield
Copper Kettle Farm - Berkshires
4 bedrooms, 10 beds
4–9 Jan
5.0 out of 5 average rating, 8 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds
23–28 Aug
4.91 out of 5 average rating, 170 reviews