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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, 127 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
12–17 Sept
4.92 out of 5 average rating, 123 reviews
Guest favourite
Cabin in Williamsburg
Retreat in the Woods
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.93 out of 5 average rating, 57 reviews
Top guest favourite
Home in Chesterfield
High Field Farm
5 bedrooms, 6 beds, 2 bathrooms
1–6 May
4.99 out of 5 average rating, 72 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
22–27 Sept
4.98 out of 5 average rating, 267 reviews
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
4.96 out of 5 average rating, 52 reviews
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
26 Sept – 1 Oct
4.95 out of 5 average rating, 320 reviews
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 153 reviews
Top guest favourite
Cabin in Williamsburg
A-frame lakeside retreat
3 bedrooms, 2 queen beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 12 reviews
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Amherst
The Suprenant House
4 bedrooms, 5 beds, 1.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 181 reviews
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
7–12 May
5.0 out of 5 average rating, 36 reviews
Guest favourite
Home in Northampton
Luxury mid-century forest home, mins from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 61 reviews
Top guest favourite
Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Becket
Cozy lakehouse
3 bedrooms, 3 beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 116 reviews
Top guest favourite
Guest house in Northampton
Cozy cottage on small intown farm.
1 bedroom, 2 beds, 1 bathroom
6–11 Dec
4.99 out of 5 average rating, 146 reviews
Home in West Springfield
BIG E! RedDoor Retreat | Fire Pit |Game Room
3 bedrooms, 3 queen beds, 1 bathroom
13–18 Sept
New place to stay
Guest favourite
Home in Northampton
Home in Northampton
3 bedrooms, 4 beds, 2.5 bathrooms
20–25 Sept
4.85 out of 5 average rating, 55 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 23 reviews