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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
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4.92 out of 5 average rating, 192 reviews
Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 bathrooms
8–13 Sept
New place to stay
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
New place to stay
Superhost
Home in Sheffield
New: Heated Pool, SIP, 1 Level Living: Sleeps 10!
3 bedrooms, 7 beds, 3 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bathroom
15–20 Oct
4.93 out of 5 average rating, 182 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.78 out of 5 average rating, 101 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
7–12 Sept
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 71 reviews
Top guest favourite
Room in Sheffield
Sheffield Lodge - Taconic Room
2 single beds, 1 bathroom
1–6 Sept
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 bathroom
26 Sept – 1 Oct
5.0 out of 5 average rating, 412 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
13–18 Sept
4.77 out of 5 average rating, 349 reviews
Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Great Barrington
King Bed | Stylish | Wi-Fi | *2m Ski Resort*
1 king bed, 1 bathroom
7–12 Sept
4.92 out of 5 average rating, 169 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Sheffield
The Blue Elm - A Historic Country Cottage
1 bedroom, 2 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 97 reviews
Guest favourite
Flat in Great Barrington
King Bed|Wi-Fi|2m Ski Resort|Studio
1 king bed, 1 bathroom
7–12 Sept
4.83 out of 5 average rating, 112 reviews
Top guest favourite
Guest suite in Salisbury
Bright & Airy Guest Suite
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 46 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 9 reviews