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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
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
22–27 Aug
4.98 out of 5 average rating, 265 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
16–21 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
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, 216 reviews
Guest favourite
Cabin in Williamsburg
Retreat in the Woods
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.93 out of 5 average rating, 56 reviews
Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 130 reviews
Top guest favourite
Guest suite in Williamsburg
Happy Maples!
1 bedroom, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 308 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
Tower in Amherst
The Silo | Rare Architectural Retreat Near UMass
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Flat in Ashfield
Zachariah House Main St. Ashfield
2 bedrooms, 2 beds, 1 bathroom
23–28 Aug
4.88 out of 5 average rating, 294 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
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
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, 485 reviews
Top guest favourite
Cabin in Plainfield
Peaceful Lakeside Cabin
1 bedroom, 1 bed, 2 bathrooms
20–25 Jun
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Flat in Northampton
Cozy Haven: Convenience & Charm
1 bedroom, 2 queen beds, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 265 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
Cottage in Ashfield
hope house
2 bedrooms, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 381 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, 410 reviews