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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
2–7 Aug
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4.98 out of 5 average rating, 124 reviews
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
5.0 out of 5 average rating, 26 reviews, 1 bedroom, 3 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Chesterfield
High Field Farm
4.99 out of 5 average rating, 67 reviews, 5 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
4.97 out of 5 average rating, 124 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
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
26–31 Jul
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
4.99 out of 5 average rating, 206 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Top guest favourite
Cabin in Cummington
Just Be Cabin
4.98 out of 5 average rating, 260 reviews, 1 bed, Toilet with sink
29 Jul – 3 Aug
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
4.99 out of 5 average rating, 147 reviews, 3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Cummington
Camp Emerson
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Ashfield
hope house
4.96 out of 5 average rating, 375 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
4.9 out of 5 average rating, 250 reviews, 1 bedroom, 2 beds, 1 bathroom
23–28 Aug
Guest favourite
Cabin in Cummington
Berkshire A-Frame Cabin!
4.85 out of 5 average rating, 131 reviews, 1 bedroom, 1 bed, 1 bathroom
5–10 Jul
Top guest favourite
Flat in Conway
Spacious, Sunny* Woodland Retreat
4.99 out of 5 average rating, 79 reviews, 1 bedroom, 3 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Ashfield
Magical, Rural Getaway in the Berkshires
4.97 out of 5 average rating, 101 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Becket
Away from it all, close to everything
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
5–10 Jul
Top guest favourite
Flat in Charlemont
Suite 23 - Spacious Sunny 2-BR with Mountain view
4.99 out of 5 average rating, 190 reviews, 2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
Guest favourite
Cottage in Otis
The lake house
4.98 out of 5 average rating, 40 reviews, 3 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
4.97 out of 5 average rating, 38 reviews, 3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
Guest favourite
Home in Northampton
Luxury mid-century forest home, mins from downtown
4.96 out of 5 average rating, 46 reviews, 3 bedrooms, 3 beds, 2 bathrooms
7–12 Aug