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Search results; Over 1,000 homes in Chesterfield

Top guest favourite
Home in Chesterfield
Charming Country Home
2 bedrooms, 3 beds, 2 private bathrooms
17–22 Aug
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4.98 out of 5 average rating, 306 reviews
Cottage in Chesterfield
Modern Luxury on the Lake
1 bedroom, 2 beds, 1 bathroom
20–25 Jul
New place to stay
Guest favourite
Home in Chesterfield
Beautiful Home near the sand at Spofford Lake!
2 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Chesterfield
Governer's Brook Camp - 2 Bedroom
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.91 out of 5 average rating, 137 reviews
Top guest favourite
Guest house in Chesterfield
House on a hill
1 bedroom, 1 bed, 1 bathroom
14–19 Aug
4.98 out of 5 average rating, 109 reviews
Top guest favourite
Room in Chesterfield
Peaceful Poet’s Farm
1 bed, 1 bathroom
8–13 Aug
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Place to stay in Chesterfield
The Ultimate Romantic Getaway
1 bed, 1 bathroom
12–17 Aug
5.0 out of 5 average rating, 62 reviews
Superhost
Tiny home in Chesterfield
Tiny Cottage on Spofford Lake
1 bedroom, 1 queen bed, 1 bathroom
15–20 Aug
Flat in Chesterfield
Lake-View Spofford Apartment w/ Shared Dock!
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
Guest favourite
Home in Chesterfield
Lakehouse Getaway
2 bedrooms, 6 beds, 1.5 bathrooms
8–13 Aug
5.0 out of 5 average rating, 9 reviews
Superhost
Home in Chesterfield
Peaceful and Private Farmhouse Retreat
3 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
New place to stay
Guest favourite
Home in Dummerston
Woodsy Retreat Near Skiing, Private Pool in Summer
2 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
4.88 out of 5 average rating, 41 reviews
Superhost
Tiny home in Chesterfield
Cottage Retreat on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Tiny home in Chesterfield
Cozy Cottage on Spofford Lake
1 bedroom, 2 beds, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 6 reviews
Superhost
Home in Guilford
Charming historic farmhouse at Tapalou Guilds Farm
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Jul
4.67 out of 5 average rating, 3 reviews
Top guest favourite
Treehouse in Putney
Treehouse Haven in Putney-All Seasons
2 beds, 1 bathroom
26–31 Jul
4.98 out of 5 average rating, 182 reviews
Top guest favourite
Cottage in Brattleboro
Forest Street Retreat Attached Guest House
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 134 reviews
Guest favourite
Loft in Vernon
Studio w/ Trail Access ~ 10 Mi to Brattleboro!
1 queen bed, 1 bathroom
9–14 Aug
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Cabin in West Brattleboro
Hidden Forest Cabin: Kitchen, Deck, Babbling Brook
3 bedrooms, 6 beds, 1 bathroom
31 Aug – 5 Sept
4.97 out of 5 average rating, 39 reviews