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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
1–6 May
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4.99 out of 5 average rating, 71 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
22–27 Aug
4.98 out of 5 average rating, 266 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
4.92 out of 5 average rating, 123 reviews
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.99 out of 5 average rating, 219 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, 130 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, 56 reviews
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, 191 reviews
Guest favourite
Cabin in Cummington
Berkshire A-Frame Cabin!
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
4.85 out of 5 average rating, 132 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, 37 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, 32 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
Home in Charlemont
Stone Ridge Cottage
2 bedrooms, 3 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.98 out of 5 average rating, 42 reviews
Guest favourite
Room in Hadley
The 1797 House/Dawson room near Amherst, Hamp
2 double beds, 1 bathroom
13–18 Sept
4.85 out of 5 average rating, 413 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, 384 reviews
Top guest favourite
Flat in Northampton
Light filled three bedroom apartment DT Florence!
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.97 out of 5 average rating, 486 reviews
Top guest favourite
Tower in Amherst
The Silo | Next to UMass & open farmland/ nature
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 23 reviews
Flat in Hatfield
Peace Meal Farm
2 bedrooms, 3 beds, 1 bathroom
5–10 Oct
New place to stay
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, 152 reviews