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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, 124 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
4–9 Aug
4.92 out of 5 average rating, 122 reviews
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
9–14 Aug
4.98 out of 5 average rating, 264 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, 69 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 213 reviews
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 30 reviews
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
New place to stay
Top guest favourite
Home in Cummington
Camp Emerson
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 15 reviews
Guest favourite
Cabin in Cummington
Berkshire A-Frame Cabin!
1 bedroom, 1 queen bed, 1 bathroom
10–15 Aug
4.85 out of 5 average rating, 132 reviews
Top guest favourite
Cottage in Ashfield
hope house
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 380 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, 79 reviews
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 317 reviews
Top guest favourite
Chalet in Peru
Swiss Chalet Style Timberframe Home in Berkshires
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.93 out of 5 average rating, 308 reviews
Top guest favourite
Cabin in Petersburg
Cozy Retreat in the Trees
2 bedrooms, 4 beds, 1 bathroom
6–11 Sept
4.94 out of 5 average rating, 280 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, 149 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, 128 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, 34 reviews
Guest favourite
Treehouse in New Marlborough
Berkshire Treehouse Retreat
3 bedrooms, 4 beds, WC
23–28 Aug
4.91 out of 5 average rating, 169 reviews