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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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Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
17–22 Sept
4.92 out of 5 average rating, 124 reviews
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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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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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Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
5–10 Oct
4.96 out of 5 average rating, 52 reviews
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Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
18–23 Oct
4.98 out of 5 average rating, 268 reviews
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Home in Middlefield
Cozy Berkshires home with brook & sugar house
3 bedrooms, 3 beds, 1 bathroom
18–23 Sept
New place to stay
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Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
26 Sept – 1 Oct
4.95 out of 5 average rating, 320 reviews
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Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 311 reviews
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Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 155 reviews
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Home in Northampton
Luxury mid-century forest home, mins from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 62 reviews
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Cabin in Williamsburg
A-frame lakeside retreat
3 bedrooms, 2 queen beds, 1 bathroom
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, 6.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 23 reviews
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Home in Becket
Cozy lakehouse
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 119 reviews
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Home in Hinsdale
Hummingbird Haven
5 bedrooms, 6 beds, 3.5 bathrooms
2–7 Oct
5.0 out of 5 average rating, 20 reviews
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Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
7–12 May
5.0 out of 5 average rating, 36 reviews
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Top guest favourite
Flat in Amherst
Suite Time in Amherst
2 bedrooms, 2 queen beds, 1 bathroom
18–23 Oct
4.97 out of 5 average rating, 71 reviews
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Farm stay in Ashfield
Sunny Chalet Nestled in the Woods of Ashfield
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 154 reviews
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Top guest favourite
Home in West Springfield
BIG E! RedDoor Retreat | Fire Pit |Game Room
3 bedrooms, 3 queen beds, 1 bathroom
11–16 Oct
5.0 out of 5 average rating, 5 reviews