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Search results; Over 1,000 homes in Chesterfield

Top guest favourite
Home in Chesterfield
High Field Farm
5 bedrooms, 6 beds, 2 private bathrooms
1–6 May
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4.99 out of 5 average rating, 71 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
22–27 Aug
4.98 out of 5 average rating, 266 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
20–25 Aug
4.92 out of 5 average rating, 123 reviews
Guest favourite
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, 50 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 219 reviews
Top guest favourite
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, 130 reviews
Guest favourite
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
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 150 reviews
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 191 reviews
Guest favourite
Home in Becket
HOT TUB! Dog & Family Friendly in the Berkshires!
2 bedrooms, 4 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 132 reviews
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 32 reviews
Top guest favourite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
1 bedroom, 2 beds, 2 bathrooms
13–18 Sept
4.95 out of 5 average rating, 482 reviews
Top guest favourite
Tent in Chester
Luxury Glamping, Private, Wood Burning Hot Tub
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Guest suite in Williamsburg
Happy Maples!
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 309 reviews
Top guest favourite
Home in Charlemont
Stone Ridge Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Cottage in Ashfield
hope house
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 384 reviews
Top guest favourite
Cabin in Florida
The Greylock Cabin
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
4.99 out of 5 average rating, 83 reviews
Top guest favourite
Tower in Amherst
The Silo | Next to UMass & open farmland/ nature
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 23 reviews
Top guest favourite
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, 152 reviews