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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, 126 reviews
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Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 51 reviews
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Cabin in Cummington
Just Be Cabin
1 double bed, WC
1–6 Sept
4.98 out of 5 average rating, 266 reviews
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Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
11–16 Sept
4.92 out of 5 average rating, 123 reviews
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Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 131 reviews
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Cabin in Williamsburg
Retreat in the Woods
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 56 reviews
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Flat in Westhampton
1800’s spacious farmhouse, beautiful outdoor area
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 76 reviews
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Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 264 reviews
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Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
24–29 Sept
4.99 out of 5 average rating, 220 reviews
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Cottage in Ashfield
hope house
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 384 reviews
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Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 8 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, 153 reviews
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Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
8–13 Sept
4.95 out of 5 average rating, 319 reviews
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Tower in Amherst
The Silo | Next to UMass & open farmland/ nature
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 30 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, 35 reviews
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Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 23 reviews
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Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 151 reviews
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Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 44 reviews
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Camper van/Motorhome in Hadley
Beautiful Country Escape
1 bedroom, 4 beds, 1 bathroom
21–26 Sept
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