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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
15–20 Sept
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4.99 out of 5 average rating, 70 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 Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
13–18 Aug
4.92 out of 5 average rating, 123 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
9–14 Sept
4.98 out of 5 average rating, 265 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, 216 reviews
Top guest favourite
Treehouse in Guilford
Cozy tent in the trees on organic flower farm
1 bedroom, 1 king bed, WC
23–28 Aug
4.99 out of 5 average rating, 199 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, 55 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, 36 reviews
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms, 5 beds, 1 bathroom
28 Sept – 3 Oct
4.89 out of 5 average rating, 9 reviews
Top guest favourite
Flat in Williamsburg
The cozy clubhouse
1 bedroom, 1 bed, 1 bathroom
7–12 Sept
4.97 out of 5 average rating, 179 reviews
Home in Shutesbury
Cute A-frame near Lake Wyola!
2 bedrooms, 4 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 5 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, 30 reviews
Top guest favourite
Home in Russell
South Quarter House
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.97 out of 5 average rating, 307 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
Guest suite in Northampton
Luxury Micro Suite ~ Charming & Peaceful Getaway
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.9 out of 5 average rating, 262 reviews
Top guest favourite
Cabin in Chesterfield
Hilltown Cabin Hideaway: A River Runs Through It!
3 bedrooms, 3 beds, 1 bathroom
26 Sept – 1 Oct
4.98 out of 5 average rating, 124 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, 381 reviews
Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 6 reviews