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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
26 Sept – 1 Oct
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4.98 out of 5 average rating, 127 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
14–19 Sept
4.92 out of 5 average rating, 124 reviews
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
27 Sept – 2 Oct
4.98 out of 5 average rating, 268 reviews
Guest favourite
Cabin in Williamsburg
Retreat in the Woods
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.93 out of 5 average rating, 57 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Guest suite in Williamsburg
Happy Maples!
1 bedroom, 2 beds, 1 bathroom
19–24 Oct
4.98 out of 5 average rating, 312 reviews
Top guest favourite
Home in Cummington
River-front home in Berkshire hills w/tennis court
4 bedrooms, 6 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Flat in Westhampton
1800’s spacious farmhouse, beautiful outdoor area
1 bedroom, 1 queen bed, 1 bathroom
15–20 Apr
4.94 out of 5 average rating, 81 reviews
Top guest favourite
Cottage in Ashfield
hope house
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 388 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, 154 reviews
Top guest favourite
Home in Goshen
Light-filled Lake House in Goshen
2 bedrooms, 3 beds, 1 bathroom
1–7 Oct
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Home in Cummington
Beautiful Secluded Country House
6 bedrooms, 11 beds, 3 bathrooms
28 Sept – 3 Oct
4.91 out of 5 average rating, 126 reviews
Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
26 Sept – 1 Oct
4.95 out of 5 average rating, 320 reviews
Featured hotel
Hotel in Northampton
Deluxe king
1 bedroom, 1 king bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Farm stay in Northampton
Hill-Ross Stables
2 bedrooms, 4 beds, 1 bathroom
21–26 Sept
4.94 out of 5 average rating, 18 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
5–10 Oct
4.99 out of 5 average rating, 222 reviews
Top guest favourite
Guest house in Northampton
Mill River Cottage (pet friendly!)
2 beds, 1 bathroom
8–13 Nov
5.0 out of 5 average rating, 442 reviews