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Search results; Over 1,000 homes in Sheffield

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Guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 private bathrooms
12–17 Oct
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4.9 out of 5 average rating, 101 reviews
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Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 bathrooms
25–30 Oct
4.98 out of 5 average rating, 55 reviews
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Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 bathrooms
1–6 Oct
4.78 out of 5 average rating, 352 reviews
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Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds, 3 bathrooms
4–9 Oct
New place to stay
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Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.78 out of 5 average rating, 101 reviews
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Guest favourite
Home in Sheffield
Serene Berkshire Artist's House
3 bedrooms, 3 beds, 2.5 bathrooms
1–6 Oct
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds, 2 bathrooms
12–17 Oct
4.97 out of 5 average rating, 29 reviews
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Superhost
Home in Sheffield
Pool Open Through Columbus Day - Sleeps 10!
3 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 bathroom
24–29 Oct
5.0 out of 5 average rating, 416 reviews
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Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 bathrooms
26–31 Oct
4.97 out of 5 average rating, 31 reviews
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Guest favourite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 bathrooms
19–24 Oct
5.0 out of 5 average rating, 27 reviews
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Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 bathrooms
1–6 Oct
5.0 out of 5 average rating, 14 reviews
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Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Oct
4.99 out of 5 average rating, 73 reviews
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Home in Sheffield
Large, light, and airy
3 bedrooms, 3 beds, 2.5 bathrooms
20–25 Oct
4.75 out of 5 average rating, 16 reviews
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Superhost
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom, 1 bathroom
1–6 Oct
4.82 out of 5 average rating, 49 reviews
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Guest favourite
Home in Sheffield
Private Berkshires Estate w/ Tennis Court
4 bedrooms, 5 beds, 3 bathrooms
26–31 Oct
4.98 out of 5 average rating, 41 reviews
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Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 10 reviews