
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

Home in Keene
4.85 out of 5 average rating, 53 reviewsLittle House with Lots to Offer
Guest favourite

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

Cabin in Guilford
4.96 out of 5 average rating, 77 reviewsGuilford Grove Cottage
Guest favourite

Guest house in Brattleboro
4.93 out of 5 average rating, 70 reviewsCasita by the Green: Quiet, Country, close to town
Top guest favourite

Guest suite in Westminster
4.96 out of 5 average rating, 55 reviewsCOZY FARMHOUSE SUITE
Guest favourite

Flat in Putney
4.97 out of 5 average rating, 98 reviewsMinimal organic hideaway inspired by nature
Guest favourite

Home in Chesterfield
4.95 out of 5 average rating, 56 reviewsThe River House
Superhost

Guest house in Winchester
4.85 out of 5 average rating, 81 reviewsThe Higgle House: A Sweetwater Farm Stay
Destinations to explore
- Boston Holiday rentals
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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Manchester Country Club - NH
- Stratton Mountain Resort
- The Shattuck Golf Club
- Magic Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Mount Sugarloaf State Reservation
- Clarksburg State Park
- Bretwood Golf Course
- Mount Tom State Reservation
- Bromley Mountain Ski Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Ekwanok Country Club
- Brattleboro Ski Hill
- Hooper Golf Course