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Search results; Over 1,000 homes in Chesterfield

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Tent in Chesterfield
Forest Platform Campsite
1 bed, 1 private bathroom
5–10 Oct
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Guest favourite
Cottage in Chesterfield
Modern Luxury on the Lake
1 bedroom, 2 beds
1–6 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Guest house in Chesterfield
House on a hill
1 bedroom, 1 bed
27 Oct – 1 Nov
4.98 out of 5 average rating, 115 reviews
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Guest favourite
Home in Chesterfield
Beautiful Home near the sand at Spofford Lake!
2 bedrooms, 6 beds
6–11 Oct
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Home in Chesterfield
Governer's Brook Camp - 2 Bedroom
2 bedrooms, 3 beds
1–6 Oct
4.9 out of 5 average rating, 146 reviews
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Guest favourite
Home in Chesterfield
Lakehouse Getaway
2 bedrooms, 6 beds
1–6 Oct
5.0 out of 5 average rating, 11 reviews
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Top guest favourite
Home in Chesterfield
Charming Country Home
2 bedrooms, 3 beds
3–8 Oct
4.98 out of 5 average rating, 318 reviews
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Guest favourite
Tiny home in Chesterfield
Cozy Cottage on Spofford Lake
1 bedroom, 2 beds
4–9 Oct
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Room in Chesterfield
Peaceful Poet’s Farm
1 queen bed
26–31 Oct
5.0 out of 5 average rating, 43 reviews
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Home in Chesterfield
Large Vacation Rental Nestled in 400 Acres
7 bedrooms, 14 single beds
1–6 Oct
New place to stay
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Superhost
Home in Chesterfield
Peaceful and Private Farmhouse Retreat
3 bedrooms, 4 beds
21–26 Oct
5.0 out of 5 average rating, 3 reviews
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Home in Westmoreland
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!
3 bedrooms, 3 beds
1–6 Oct
4.93 out of 5 average rating, 14 reviews
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Camper van/Motorhome in Chesterfield
Vintage Cruiser on Spofford Lake
1 bedroom, 2 beds
4–9 Oct
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Guest favourite
Tiny home in Chesterfield
Honeymoon Cottage at the Lake
1 bedroom, 2 beds
4–9 Oct
5.0 out of 5 average rating, 8 reviews
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Guest favourite
Guest house in Brattleboro
Casita by the Green: Quiet, Country, close to town
1 bedroom, 2 beds
1–6 Oct
4.94 out of 5 average rating, 77 reviews
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Guest favourite
Cottage in Chesterfield
Tiny Cottage on Spofford Lake
1 bedroom, 1 queen bed
2–7 Oct
5.0 out of 5 average rating, 11 reviews
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Guest favourite
Room in Chesterfield
Waterfront Paradise - 1.3 mile to Brattleboro
2 beds
1–6 Oct
4.93 out of 5 average rating, 69 reviews
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Guest favourite
Cottage in Chesterfield
Cottage on Spofford Lake “Barn”
1 bedroom, 3 beds
1–6 Oct
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Apartment in Putney
Gorgeous, new apartment laundry
1 queen bed
1–8 Oct
4.7 out of 5 average rating, 10 reviews