filters

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
,
4.98 out of 5 average rating, 126 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
11–16 Sept
4.92 out of 5 average rating, 123 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
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
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
Cabin in Cummington
Just Be Cabin
1 double bed, WC
9–14 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
9–14 Sept
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, 152 reviews
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 4 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 Cummington
River-front home in Berkshire hills w/tennis court
4 bedrooms, 6 beds, 3 bathrooms
9–14 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Flat in Ashfield
Zachariah House Main St. Ashfield
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.88 out of 5 average rating, 295 reviews
Guest favourite
Home in Northampton
Luxury mid-century forest home, mins from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 59 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
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
Guest favourite
Home in Ashfield
Cocoa House
3 bedrooms, 6 beds, 1.5 bathrooms
9–14 Sept
5.0 out of 5 average rating, 28 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
Top guest favourite
Home in North Adams
Steps to MoCA private house + SAUNA!
4 bedrooms, 6 beds, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 559 reviews