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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
13–18 Sept
4.92 out of 5 average rating, 124 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed
13–18 Sept
4.98 out of 5 average rating, 267 reviews
Guest favourite
Cabin in Williamsburg
Retreat in the Woods
1 bedroom, 2 beds
1–6 Nov
4.93 out of 5 average rating, 57 reviews
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed
19–24 Oct
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Guest suite in Williamsburg
Happy Maples!
1 bedroom, 2 beds
19–24 Oct
4.98 out of 5 average rating, 312 reviews
Top guest favourite
Flat in Westhampton
1800’s spacious farmhouse, beautiful outdoor area
1 bedroom, 1 queen bed
15–20 Apr
4.94 out of 5 average rating, 80 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds
26–31 Oct
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Home in Goshen
Light-filled Lake House in Goshen
2 bedrooms, 3 beds
1–7 Oct
5.0 out of 5 average rating, 37 reviews
Top guest favourite
Home in Cummington
River-front home in Berkshire hills w/tennis court
4 bedrooms, 6 beds
14–20 Sept
5.0 out of 5 average rating, 19 reviews
Bed and breakfast in Worthington
The Carriage Room - Goldenrod Country Inn
1 bedroom, 1 bed
27 Sept – 2 Oct
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Farm stay in Ashfield
Sunny Chalet Nestled in the Woods of Ashfield
3 bedrooms, 5 beds
20–25 Sept
5.0 out of 5 average rating, 154 reviews
Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds
21–26 Sept
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Cummington
Beautiful Secluded Country House
6 bedrooms, 11 beds
28 Sept – 3 Oct
4.91 out of 5 average rating, 126 reviews
Guest favourite
Flat in Northampton
Nature Nook
1 queen bed
28 Oct – 2 Nov
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds
26 Sept – 1 Oct
4.95 out of 5 average rating, 320 reviews
Top guest favourite
Flat in Northampton
Cozy Haven: Convenience & Charm
1 bedroom, 2 queen beds
18–23 Oct
4.99 out of 5 average rating, 273 reviews
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds
13–18 Sept
4.99 out of 5 average rating, 153 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds
5–10 Oct
4.99 out of 5 average rating, 222 reviews