Search results; Over 1,000 homes in Sheffield

Guest favourite
Nature lodge in Sheffield
Sheffield Lodge - Ramblewood Master
1 bedroom, 1 bed, 1 private bathroom
5–10 Jul
,
4.98 out of 5 average rating, 57 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
6–11 Jul
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds, 2 bathrooms
4–9 Jul
4.97 out of 5 average rating, 32 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
24–29 Aug
4.79 out of 5 average rating, 100 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
15–20 Jul
4.78 out of 5 average rating, 341 reviews
Guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds, 2 bathrooms
13–18 Jul
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Sheffield
Luxury, Romantic, Timeless Berkshires: Sleeps 18!
8 bedrooms, 11 beds, 4.5 bathrooms
7–12 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 bathrooms
3–8 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 26 reviews
Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds, 2.5 bathrooms
6–11 Jul
4.82 out of 5 average rating, 33 reviews
Guest favourite
Home in Sheffield
Ashley Falls Home w/ Fire Pit: Hike & Ski!
5 bedrooms, 6 beds, 3 bathrooms
24–29 Aug
4.94 out of 5 average rating, 47 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 403 reviews
Top guest favourite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 bathrooms
21–26 Sept
4.99 out of 5 average rating, 130 reviews
Superhost
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
4–9 Jul
New place to stay
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bathroom
27 Aug – 1 Sept
4.94 out of 5 average rating, 176 reviews
Guest favourite
Home in Sheffield
Serene Berkshire Artist's House
3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Jul
4.99 out of 5 average rating, 69 reviews