
Holiday rentals in Chesterfield
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Top-rated holiday rentals in Chesterfield
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Chesterfield holiday rentals
Other great holiday rentals in Chesterfield
Guest favourite

Holiday home in Chesterfield
5 out of 5 average rating, 20 reviewsSpofford lake 1 bedroom apartment with boat dock
Top guest favourite

Yurt in Hinsdale
5 out of 5 average rating, 21 reviewsRecharge in a yurt at REST Farm
Guest favourite

Cottage in Chesterfield
5 out of 5 average rating, 5 reviewsTiny Cottage on Spofford Lake
Guest favourite

Home in Putney
4.95 out of 5 average rating, 22 reviews19th Century Farmhouse Retreat
Guest favourite

Cabin in Winchester
4.87 out of 5 average rating, 31 reviewsThe Ironclad Mountain Retreat
Guest favourite

Home in Chesterfield
4.95 out of 5 average rating, 57 reviewsThe River House
Guest favourite

Cottage in Brattleboro
4.97 out of 5 average rating, 35 reviewsOn the Water at North Bridge Cove
Guest favourite

Home in Brattleboro
5 out of 5 average rating, 16 reviewsHiking Retreat with Sauna in the Brattleboro Hills
Destinations to explore
- Boston Holiday rentals
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Pats Peak Ski Area
- Manchester Country Club - NH
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Bromley Mountain Ski Resort
- Mount Sugarloaf State Reservation
- Clarksburg State Park
- Mount Tom State Reservation
- Bretwood Golf Course
- Fox Run Golf Club
- Baker Hill Golf Club
- Brattleboro Ski Hill
- Crotched Mountain Ski and Ride
- Hooper Golf Course