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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
26 Sept – 1 Oct
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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
18–23 Sept
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
1–6 May
4.99 out of 5 average rating, 73 reviews
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Guest favourite
Cabin in Williamsburg
Retreat in the Woods
1 bedroom, 2 beds
1–6 Nov
4.93 out of 5 average rating, 57 reviews
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Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed
18–23 Oct
4.98 out of 5 average rating, 268 reviews
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Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed
19–24 Oct
4.96 out of 5 average rating, 52 reviews
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Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 320 reviews
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Guest favourite
Home in Northampton
Luxury mid-century forest home, mins from downtown
3 bedrooms, 3 queen beds
20–25 Sept
4.95 out of 5 average rating, 62 reviews
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Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds
20–25 Sept
4.99 out of 5 average rating, 155 reviews
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Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds
20–25 Sept
4.93 out of 5 average rating, 311 reviews
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Home in Middlefield
Cozy Berkshires home with brook & sugar house
3 bedrooms, 3 beds
20–25 Sept
New place to stay
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Top guest favourite
Cabin in Williamsburg
A-frame lakeside retreat
3 bedrooms, 2 queen beds
21–26 Sept
5.0 out of 5 average rating, 13 reviews
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Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds
26–31 Oct
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds
7–12 May
5.0 out of 5 average rating, 37 reviews
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Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Hinsdale
Hummingbird Haven
5 bedrooms, 6 beds
2–7 Oct
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Home in Cummington
River-front home in Berkshire hills w/tennis court
4 bedrooms, 6 beds
19–24 Sept
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Home in Ashfield
Cocoa House
3 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 28 reviews