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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
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
13–18 Jul
4.92 out of 5 average rating, 122 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, 67 reviews
Guest favourite
Home in Windsor
Beautiful Log Cabin with a Mountain View
3 bedrooms, 3 beds, 1 bathroom
1–6 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Northampton
Luxury mid-century forest home, mins from downtown
3 bedrooms, 3 queen beds, 2 bathrooms
2–7 Jul
4.96 out of 5 average rating, 45 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, 146 reviews
Guest favourite
Home in Goshen
Lake Escape
2 bedrooms, 3 beds, 1 bathroom
9–14 Mar
4.97 out of 5 average rating, 143 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, Toilet with sink
26–31 Jul
4.98 out of 5 average rating, 257 reviews
Guest favourite
Home in Worthington
Morning Side
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Jul
5.0 out of 5 average rating, 9 reviews
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, 7 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, 204 reviews
Top guest favourite
Guest house in Shelburne Falls
Shelburne Guest House -The Ranch
3 bedrooms, 3 beds, 1 bathroom
7–12 Jul
5.0 out of 5 average rating, 308 reviews
Home in Becket
Away from it all, close to everything
3 bedrooms, 3 queen beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Northampton
Clean and sunny house near Smith College
3 bedrooms, 4 beds, 2 bathrooms
17–22 Aug
4.94 out of 5 average rating, 289 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
Place to stay in Northampton
Solar Powered Home near Look Park Room 2 Basement
1 bedroom, 3 beds, 1 bathroom
28 Jul – 2 Aug
4.97 out of 5 average rating, 165 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, 121 reviews