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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
1 double bed, WC
29 Jul – 3 Aug
4.98 out of 5 average rating, 262 reviews
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 29 reviews
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
26–31 Jul
4.92 out of 5 average rating, 122 reviews
Top guest favourite
Home in Chesterfield
High Field Farm
5 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
15–20 Aug
4.97 out of 5 average rating, 125 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 208 reviews
Top guest favourite
Home in Cummington
Camp Emerson
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 148 reviews
Top guest favourite
Home in Charlemont
Stone Ridge Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.9 out of 5 average rating, 252 reviews
Top guest favourite
Farm stay in Worthington
Like sleeping on a cloud
2 bedrooms, 3 beds, 3 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Conway
Spacious, Sunny* Woodland Retreat
1 bedroom, 3 beds, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 79 reviews
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
4.94 out of 5 average rating, 181 reviews
Top guest favourite
Cabin in Florida
The Greylock Cabin
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.99 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 313 reviews
Top guest favourite
Tent in Chester
Luxury Glamping, Private, Wood Burning Hot Tub
2 bedrooms, 2 queen beds, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 32 reviews