filters

Search results; Over 1,000 homes in Sheffield

Photo 1 of 29
Top guest favourite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 private bathrooms
8–13 Dec
,
4.99 out of 5 average rating, 133 reviews
Photo 1 of 29
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
Photo 1 of 27
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
22–27 Sept
4.98 out of 5 average rating, 55 reviews
Photo 1 of 29
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds
16–21 Sept
New place to stay
Photo 1 of 21
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
Photo 1 of 29
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds
23–28 Sept
4.78 out of 5 average rating, 352 reviews
Photo 1 of 29
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, 31 reviews
Photo 1 of 16
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds
19–24 Oct
5.0 out of 5 average rating, 27 reviews
Photo 1 of 29
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds
16–21 Sept
4.97 out of 5 average rating, 29 reviews
Photo 1 of 29
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
Photo 1 of 29
Guest favourite
Home in Sheffield
Serene Berkshire Artist's House
3 bedrooms, 3 beds
16–21 Sept
4.99 out of 5 average rating, 69 reviews
Photo 1 of 28
Guest favourite
Home in Sheffield
Perfect Peaceful Berkshire Location !
2 bedrooms, 2 queen beds
24–29 Sept
4.92 out of 5 average rating, 131 reviews
Photo 1 of 24
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds
16–21 Sept
5.0 out of 5 average rating, 9 reviews
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds
28 Sept – 3 Oct
4.99 out of 5 average rating, 73 reviews
Photo 1 of 29
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, 194 reviews
Photo 1 of 29
Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds
21–26 Sept
New place to stay
Photo 1 of 27
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds
24–29 Oct
5.0 out of 5 average rating, 416 reviews
Photo 1 of 24
Superhost
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom
17–22 Sept
4.82 out of 5 average rating, 49 reviews