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Search results; Over 1,000 homes in Sheffield

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Top guest favorite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 private bath
Oct 24 – 29
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5.0 out of 5 average rating, 416 reviews
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Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds, 2 baths
Oct 1 – 6
4.78 out of 5 average rating, 101 reviews
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Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds, 3 baths
Oct 1 – 6
4.78 out of 5 average rating, 352 reviews
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Guest favorite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds, 2 baths
Oct 25 – 30
4.98 out of 5 average rating, 55 reviews
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Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds, 3 baths
Oct 4 – 9
New place to stay
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Guest favorite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds, 2 baths
Oct 12 – 17
4.9 out of 5 average rating, 101 reviews
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Top guest favorite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds, 2 baths
Oct 26 – 31
4.97 out of 5 average rating, 31 reviews
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Guest favorite
Barn in Sheffield
Modern Dairy Barn
4 bedrooms, 5 beds, 3 baths
Oct 19 – 24
5.0 out of 5 average rating, 27 reviews
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Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds, 4 baths
Oct 1 – 6
New place to stay
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Guest favorite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds, 3.5 baths
Oct 4 – 9
5.0 out of 5 average rating, 9 reviews
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Guest favorite
Home in Sheffield
Serene Berkshire Artist's House
3 bedrooms, 3 beds, 2.5 baths
Oct 1 – 6
4.99 out of 5 average rating, 69 reviews
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Top guest favorite
Home in Sheffield
The Kellogg House in the Heart of The Berkshires
2 bedrooms, 2 queen beds, 1 bath
Oct 1 – 6
4.99 out of 5 average rating, 73 reviews
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Top guest favorite
Home in Sheffield
52-Acre Berkshires Farmhouse • Fire Pit + Trails
4 bedrooms, 9 beds, 2.5 baths
Oct 1 – 6
5.0 out of 5 average rating, 14 reviews
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Top guest favorite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds, 2 baths
Oct 12 – 17
4.97 out of 5 average rating, 29 reviews
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Top guest favorite
Home in Sheffield
Belle Meade
2 bedrooms, 2 beds, 2 baths
Dec 8 – 13
4.99 out of 5 average rating, 133 reviews
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Superhost
Home in Sheffield
Pool Open Through Columbus Day - Sleeps 10!
3 bedrooms, 7 beds, 3 baths
Oct 1 – 6
New place to stay
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Superhost
Home in Sheffield
Whitney by AvantStay | Private Berkshires Estate
5 bedrooms, 7 beds, 2.5 baths
Nov 9 – 14
4.83 out of 5 average rating, 36 reviews
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Guest favorite
Home in Sheffield
Ashley Falls Home w/ Fire Pit: Hike & Ski!
5 bedrooms, 6 beds, 3 baths
Oct 26 – 31
4.9 out of 5 average rating, 51 reviews
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Home in Sheffield
Water-View Home in the Berkshires
3 bedrooms, 4 beds, 2 baths
Oct 17 – 22
4.95 out of 5 average rating, 39 reviews