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Search results; Over 1,000 homes in Chesterfield

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Top guest favourite
Cabin in Chesterfield
Hilltown Cabin Hideaway: A River Runs Through It!
3 bedrooms, 3 beds, 1 private bathroom
1–6 May
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4.98 out of 5 average rating, 127 reviews
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Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
3–8 Oct
4.92 out of 5 average rating, 124 reviews
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Top guest favourite
Home in Chesterfield
High Field Farm
5 bedrooms, 6 beds, 2 bathrooms
1–6 May
4.99 out of 5 average rating, 73 reviews
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Home in Cummington
Beautiful Secluded Country House
6 bedrooms, 11 beds, 3 bathrooms
1–6 Oct
4.91 out of 5 average rating, 127 reviews
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Cabin in Cummington
Just Be Cabin
1 double bed, WC
18–23 Oct
4.98 out of 5 average rating, 270 reviews
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Home in Worthington
Extraordinary Berkshires Estate & Carriage House
9 bedrooms, 21 beds, 7.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 20 reviews
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Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 24 reviews
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Flat in Sunderland
A Cozy Condo Near Horse Farm + Mount Sugarloaf
4 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 8 reviews
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Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
4.96 out of 5 average rating, 52 reviews
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Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 156 reviews
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Home in Cummington
River-front home in Berkshire hills w/tennis court
4 bedrooms, 6 beds, 3 bathrooms
4–9 Oct
5.0 out of 5 average rating, 19 reviews
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Cabin in Williamsburg
Retreat in the Woods
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.93 out of 5 average rating, 57 reviews
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Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 320 reviews
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Villa in Whately
Valley View Post & Beam Villa
6 bedrooms, 8 beds, 3.5 bathrooms
22–27 Oct
4.99 out of 5 average rating, 80 reviews
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Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds, 2 bathrooms
30 Nov – 5 Dec
4.93 out of 5 average rating, 311 reviews
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Cabin in Williamsburg
Little Blue 2
2 bedrooms, 4 beds, 1 bathroom
4–9 Jan
5.0 out of 5 average rating, 8 reviews
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Home in Goshen
Light-filled Lake House in Goshen
2 bedrooms, 3 beds, 1 bathroom
1–7 Oct
5.0 out of 5 average rating, 37 reviews
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Home in Northampton
Home in Northampton
3 bedrooms, 4 beds, 2.5 bathrooms
16–21 Nov
4.86 out of 5 average rating, 56 reviews