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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
21–26 Aug
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4.98 out of 5 average rating, 124 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
26–31 Jul
4.92 out of 5 average rating, 122 reviews
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Chesterfield
High Field Farm
5 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 147 reviews
Top guest favourite
Cabin in Williamsburg
A-frame lakeside retreat
3 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Worthington
Extraordinary Berkshires Estate & Carriage House
9 bedrooms, 21 beds, 7.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.97 out of 5 average rating, 125 reviews
Guest favourite
Home in Goshen
Lake Escape
2 bedrooms, 3 beds, 1 bathroom
9–14 Mar
4.97 out of 5 average rating, 144 reviews
Guest favourite
Tiny home in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.96 out of 5 average rating, 49 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, Toilet with sink
29 Jul – 3 Aug
4.98 out of 5 average rating, 260 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 207 reviews
Guest favourite
Home in Cummington
Beautiful Secluded Country House
6 bedrooms, 11 beds, 3 bathrooms
14–19 Aug
4.91 out of 5 average rating, 122 reviews
Guest favourite
Villa in Whately
Valley View Post & Beam Villa
6 bedrooms, 8 beds, 3.5 bathrooms
9–14 Aug
4.99 out of 5 average rating, 79 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, 21 reviews
Guest favourite
Home in Ashfield
Cocoa House
3 bedrooms, 6 beds, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Ashfield
An 18th century farmhouse
2 bedrooms, 2 beds, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 96 reviews
Guest favourite
Flat in Ashfield
Zachariah House Main St. Ashfield
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.88 out of 5 average rating, 290 reviews
Top guest favourite
Home in Becket
Cozy lakehouse
3 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 108 reviews