filters

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
,
4.92 out of 5 average rating, 192 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
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
14–19 Sept
4.99 out of 5 average rating, 69 reviews
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds
7–12 Sept
New place to stay
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
7–12 Sept
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds
23–28 Aug
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds
25–30 Sept
4.9 out of 5 average rating, 99 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, 349 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
Home in Sheffield
Peaceful and Private Setting
3 bedrooms, 6 beds
7–12 Sept
4.95 out of 5 average rating, 38 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
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds
23–28 Aug
4.96 out of 5 average rating, 27 reviews
Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds
28 Aug – 2 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Flat in Great Barrington
King Bed|2m Ski Resort|Stylish|Fast Wi-Fi
1 king bed
23–28 Aug
4.89 out of 5 average rating, 91 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, 411 reviews
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds
30 Aug – 4 Sept
New place to stay
Top guest favourite
Home in Sheffield
Great Berkshire Getaway !
1 bedroom, 1 queen bed
8–13 Sept
4.95 out of 5 average rating, 115 reviews