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Search results; Over 1,000 homes in Chesterfield

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Top guest favourite
Cabin in Chesterfield
Hilltown Cabin Hideaway: A River Runs Through It!
3 bedrooms, 3 beds, 1 private bathroom
1–6 May
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4.98 out of 5 average rating, 127 reviews
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Cabin in Cummington
Just Be Cabin
1 double bed, WC
18–23 Oct
4.98 out of 5 average rating, 269 reviews
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Home in Chesterfield
High Field Farm
5 bedrooms, 6 beds, 2 bathrooms
1–6 May
4.99 out of 5 average rating, 73 reviews
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Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
3–8 Oct
4.92 out of 5 average rating, 124 reviews
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Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom, 1 queen bed, 1 bathroom
19–24 Oct
4.96 out of 5 average rating, 52 reviews
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Guest favourite
Cabin in Williamsburg
Retreat in the Woods
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.93 out of 5 average rating, 57 reviews
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Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
3–8 Nov
4.97 out of 5 average rating, 133 reviews
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Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.99 out of 5 average rating, 156 reviews
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Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms, 4 beds, 2 bathrooms
11–16 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.99 out of 5 average rating, 222 reviews
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Top guest favourite
Farm stay in Whately
Beautiful 18th Century Farmhouse
3 bedrooms, 3 double beds, 2.5 bathrooms
7–12 Nov
5.0 out of 5 average rating, 41 reviews
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Home in Cummington
Camp Emerson
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 16 reviews
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Guest favourite
Home in Ashfield
An 18th century farmhouse
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 109 reviews
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Top guest favourite
Tent in Chester
Luxury Glamping, Private, Wood Burning Hot Tub
2 bedrooms, 2 beds, 1 bathroom
23–28 Oct
5.0 out of 5 average rating, 43 reviews
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Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
7–12 May
5.0 out of 5 average rating, 37 reviews
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Home in Worthington
Morning Side
3 bedrooms, 4 beds, 2.5 bathrooms
15–20 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Cummington
Beautiful Secluded Country House
6 bedrooms, 11 beds, 3 bathrooms
1–6 Oct
4.91 out of 5 average rating, 126 reviews
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Guest favourite
Home in Ashfield
Cocoa House
3 bedrooms, 6 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 28 reviews