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Search results; Over 1,000 homes in Sheffield

Top Guest favourite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 private bath
26 Sept – 1 Oct
,
5.0 out of 5 average rating, 413 reviews
Top Guest favourite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 baths
2–7 Nov
4.99 out of 5 average rating, 133 reviews
Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 baths
7–12 Sept
4.78 out of 5 average rating, 101 reviews
Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 baths
8–13 Sept
New place to stay
Top Guest favourite
Apartment in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed, 1 bath
20–25 Oct
4.93 out of 5 average rating, 183 reviews
Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 baths
7–12 Sept
4.98 out of 5 average rating, 55 reviews
Top Guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds, 2 baths
7–12 Sept
4.96 out of 5 average rating, 28 reviews
Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 baths
7–12 Sept
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Sheffield
Serene Berkshire Artist's House
3 bedrooms, 3 beds, 2.5 baths
7–12 Sept
4.99 out of 5 average rating, 69 reviews
Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 baths
14–19 Sept
5.0 out of 5 average rating, 9 reviews
Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 baths
13–18 Sept
4.77 out of 5 average rating, 350 reviews
Top Guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 baths
1–6 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds, 2.5 baths
13–18 Sept
4.92 out of 5 average rating, 192 reviews
Guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 baths
12–17 Sept
5.0 out of 5 average rating, 12 reviews
Top Guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 baths
25–30 Sept
4.9 out of 5 average rating, 99 reviews
Guest favourite
Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds, 2 baths
6–11 Sept
4.95 out of 5 average rating, 38 reviews
Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds, 3 baths
7–12 Sept
New place to stay
Superhost
Home in New Marlborough
Heated pool, Screened Sun Room, Privacy, Sleeps 9
3 bedrooms, 6 beds, 3 baths
15–20 Sept
New place to stay
Guest favourite
Home in Sheffield
Peaceful and Private Setting
3 bedrooms, 6 beds, 3 baths
7–12 Sept
4.95 out of 5 average rating, 38 reviews
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