Search results; Over 1,000 homes in Sheffield

Top guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Monument Room
1 bedroom, 1 bed, 1 private bathroom
31 Aug – 5 Sept
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4.94 out of 5 average rating, 77 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 beds
27 Jul – 1 Aug
4.98 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
2 beds
24–29 Aug
5.0 out of 5 average rating, 405 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 queen beds
2–7 Aug
4.98 out of 5 average rating, 65 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
9 beds
6–11 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 beds
26–31 Jul
4.96 out of 5 average rating, 25 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
5 beds
19–24 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Washington Room
1 double bed
19–24 Jul
4.93 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 queen bed
27 Aug – 1 Sept
4.94 out of 5 average rating, 178 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
8 beds
9–14 Aug
4.78 out of 5 average rating, 344 reviews
Superhost
Guest house in Sheffield
The Cottage at 3 Sisters Farm
2 queen beds
2–7 Aug
4.83 out of 5 average rating, 12 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
5 beds
24–29 Aug
4.79 out of 5 average rating, 100 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
4 beds
23–28 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Guest suite in Sheffield
The Sunset Suite~Great South Berkshire Location!
1 queen bed
1–6 Aug
5.0 out of 5 average rating, 92 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 beds
31 Aug – 5 Sept
4.94 out of 5 average rating, 181 reviews
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 beds
5–10 Aug
4.9 out of 5 average rating, 97 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
2 beds
6–11 Aug
5.0 out of 5 average rating, 94 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
8 beds
19–24 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 king beds
14–19 Sept
4.98 out of 5 average rating, 41 reviews