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Search results; Over 1,000 homes in Chesterfield

Top guest favourite
Cabin in Chesterfield
Hilltown Cabin Hideaway: A River Runs Through It!
3 bedrooms, 3 beds, 1 private bathroom
21–26 Aug
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4.98 out of 5 average rating, 124 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
4.98 out of 5 average rating, 263 reviews, 1 bed, WC
18–23 Aug
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
4.99 out of 5 average rating, 207 reviews, 1 bedroom, 2 beds, 1 bathroom
27 Jul – 1 Aug
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
4.96 out of 5 average rating, 49 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Aug
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
5.0 out of 5 average rating, 30 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 Aug
Top guest favourite
Room in Northampton
Warm Country Home Minutes from Town
4.95 out of 5 average rating, 906 reviews, 1 queen bed, 1 bathroom
23–28 Aug
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
4.92 out of 5 average rating, 122 reviews, 1 bedroom, 3 beds, 1 bathroom
31 Jul – 5 Aug
Top guest favourite
Room in Cummington
Spacious private BR with king bed in Cummington
4.97 out of 5 average rating, 68 reviews, 1 king bed, 1 bathroom
26–31 Jul
Top guest favourite
Guest suite in Williamsburg
Happy Maples!
4.98 out of 5 average rating, 304 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
4.99 out of 5 average rating, 148 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
4.9 out of 5 average rating, 252 reviews, 1 bedroom, 2 beds, 1 bathroom
23–28 Aug
Top guest favourite
Room in Northampton
Serene getaway near Smith & Main St
4.99 out of 5 average rating, 676 reviews, 1 bed, 1 bathroom
4–9 Oct
Top guest favourite
Flat in Williamsburg
The cozy clubhouse
4.97 out of 5 average rating, 174 reviews, 1 bedroom, 1 bed, 1 bathroom
6–11 Sept
Guest favourite
Cabin in Cummington
Berkshire A-Frame Cabin!
4.85 out of 5 average rating, 132 reviews, 1 bedroom, 1 bed, 1 bathroom
21–26 Jul
Top guest favourite
Home in Williamsburg
Hilltown Studio
4.99 out of 5 average rating, 222 reviews, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Home in Chesterfield
High Field Farm
4.99 out of 5 average rating, 68 reviews, 5 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
4.97 out of 5 average rating, 127 reviews, 1 bedroom, 1 bed, 1 bathroom
15–20 Aug
Top guest favourite
Home in Cummington
Camp Emerson
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Ashfield
An 18th century farmhouse
4.98 out of 5 average rating, 98 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept