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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
,
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
7–12 Aug
4.92 out of 5 average rating, 122 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
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
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.99 out of 5 average rating, 214 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
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, 5 reviews
Top guest favourite
Flat in Williamsburg
The cozy clubhouse
1 bedroom, 1 bed, 1 bathroom
6–11 Sept
4.97 out of 5 average rating, 177 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
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
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
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
Home in Shutesbury
Cute A-frame near Lake Wyola!
2 bedrooms, 4 beds, 1 bathroom
13–18 Sept
New place to stay
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.94 out of 5 average rating, 187 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
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 150 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
Tiny home in Northampton
Tiny House Farm Retreat: Mountain Views, Fire pit
1 bed, 1 bathroom
9–14 Aug
4.98 out of 5 average rating, 299 reviews