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Search results; Over 1,000 homes in Sheffield

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Top guest favourite
Flat in Sheffield
Hideaway with Spectacular Berkshire Views
1 bedroom, 2 beds, 1 private bathroom
24–29 Oct
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5.0 out of 5 average rating, 416 reviews
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Home in Sheffield
Berkshire Lake Hideaway
3 bedrooms, 5 beds
16–21 Sept
New place to stay
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Cabin in Sheffield
Log Cabin - playroom, fireplace, skiing - $0 fees
4 bedrooms, 8 beds
17–22 Sept
4.78 out of 5 average rating, 352 reviews
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Top guest favourite
Flat in Sheffield
Private Berkshire Barn Apartment
1 bedroom, 1 queen bed
4–9 Nov
4.93 out of 5 average rating, 184 reviews
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Cottage in Sheffield
Charming Handcrafted Cottage in the Berkshires!
3 bedrooms, 5 beds
28 Sept – 3 Oct
4.78 out of 5 average rating, 101 reviews
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Top guest favourite
Home in Sheffield
Beautiful Berkshires Home | Perfect For 3 Families
4 bedrooms, 9 beds
16–21 Sept
4.97 out of 5 average rating, 29 reviews
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Guest favourite
Cottage in Sheffield
Cheerful 3-bedroom cottage with woodstove.
3 bedrooms, 3 beds
20–25 Sept
4.92 out of 5 average rating, 193 reviews
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Top guest favourite
Home in Sheffield
Family friendly house with fenced yard & fire pit
3 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 31 reviews
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Guest favourite
Home in Sheffield
Serene Berkshire Artist's House
3 bedrooms, 3 beds
16–21 Sept
4.99 out of 5 average rating, 69 reviews
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Top guest favourite
Home in Sheffield
House Among Trees - A Perfect Holiday Getaway
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.93 out of 5 average rating, 98 reviews
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Guest favourite
Home in Sheffield
Berkshire Getaway~ No Pet Fee! Walk to Distillery
3 bedrooms, 3 beds
12–17 Oct
4.9 out of 5 average rating, 101 reviews
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Superhost
Home in Sheffield
Pool Open Through Columbus Day - Sleeps 10!
3 bedrooms, 7 beds
16–21 Sept
New place to stay
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Superhost
Home in Sheffield
Timber Frame • Big Deck • Game Room | Near Trails
4 bedrooms, 6 beds
21–26 Sept
New place to stay
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Top guest favourite
Home in New Marlborough
Grand View
4 bedrooms, 5 beds
18–23 Sept
4.98 out of 5 average rating, 57 reviews
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Guest favourite
Home in Sheffield
Bull Hill Bungalow
3 bedrooms, 3 beds
22–27 Sept
4.98 out of 5 average rating, 55 reviews
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Guest favourite
Home in Sheffield
Berkshires Retreat w/ Pickleball – for Big Groups!
7 bedrooms, 8 beds
16–21 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Sheffield
All new mountain retreat near Great Barrington.
3 bedrooms, 5 beds
17–22 Sept
5.0 out of 5 average rating, 10 reviews
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Superhost
Home in Sheffield
Cozy Cottage Route 7 Sheffield
1 bedroom
16–21 Sept
4.82 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Great Barrington
The Hideaway: Berkshire Home - village of Egremont
3 bedrooms, 7 beds
16–21 Sept
4.95 out of 5 average rating, 148 reviews