Search results; Over 1,000 homes in Chesterfield

Top guest favourite
Cabin in Chesterfield
Hilltown Cabin Hideaway: A River Runs Through It!
3 bedrooms, 3 beds, 1 private bathroom
21–26 Aug
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4.98 out of 5 average rating, 124 reviews
Top guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed, Toilet with sink
26–31 Jul
4.98 out of 5 average rating, 257 reviews
Top guest favourite
Treehouse in Williamsburg
Cozy & Relaxing Stay in Craftsman's Treehouse
1 bedroom, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Chesterfield
High Field Farm
5 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
4.99 out of 5 average rating, 67 reviews
Guest favourite
Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
3 bedrooms, 4 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Camper van/Motorhome in Westhampton
AirbytheStream waterfront, private, clean and cozy
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.9 out of 5 average rating, 249 reviews
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom, 3 beds, 1 bathroom
13–18 Jul
4.92 out of 5 average rating, 122 reviews
Top guest favourite
Cottage in Ashfield
hope house
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 374 reviews
Top guest favourite
Cabin in Williamsburg
Mountain Retreat close to Northampton & Amherst!
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.97 out of 5 average rating, 121 reviews
Guest favourite
Home in Williamsburg
Cute and Cozy Lake Cottage
2 bedrooms, 2 double beds, 1 bathroom
10–15 Jul
4.86 out of 5 average rating, 50 reviews
Top guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 146 reviews
Top guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms, 2 double beds, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 311 reviews
Top guest favourite
Flat in Northampton
Sunny Peaceful Home
1 queen bed, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 689 reviews
Top guest favourite
Flat in Westhampton
1800’s spacious farmhouse, beautiful outdoor area
1 bedroom, 1 queen bed, 1 bathroom
27 Jul – 1 Aug
4.93 out of 5 average rating, 72 reviews
Top guest favourite
Tent in Chester
Luxury Glamping, Private, Wood Burning Hot Tub
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Flat in Northampton
Light filled three bedroom apartment DT Florence!
3 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 472 reviews
Top guest favourite
Room in Northampton
Warm Country Home Minutes from Town
1 queen bed, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 895 reviews
Top guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 203 reviews