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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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Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, WC
18–23 Oct
4.98 out of 5 average rating, 270 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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Top guest favourite
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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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, 24 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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Guest favourite
Home in Worthington
Extraordinary Berkshires Estate & Carriage House
9 bedrooms, 21 beds, 7.5 bathrooms
1–6 Nov
5.0 out of 5 average rating, 20 reviews
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Guest favourite
Home in Goshen
Lake Escape
2 bedrooms, 3 beds, 1 bathroom
6–11 Jun
4.97 out of 5 average rating, 146 reviews
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Featured hotel
Hotel in Northampton
The Ellery, Deluxe king
1 bedroom, 1 king bed, 1 bathroom
10–15 Oct
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Cabin in Williamsburg
Little Blue 2
2 bedrooms, 4 beds, 1 bathroom
4–9 Jan
5.0 out of 5 average rating, 8 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
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
Home in Cummington
Camp Emerson
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
5.0 out of 5 average rating, 17 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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Home in Charlemont
3 Bedroom 2 Bath Cottage on The Brook
3 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
New place to stay
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Superhost
Cabin in Sandisfield
The Lucas Cabin-Cozy Riverfront Getaway
2 bedrooms, 4 double beds, 1 bathroom
4–9 Oct
New place to stay
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Guest favourite
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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Guest favourite
Home in Chester
Riverhouse! Peak Foliage October 10-24
2 bedrooms, 5 beds, 1 bathroom
4–9 Oct
4.92 out of 5 average rating, 13 reviews