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Search results; Over 1,000 places in Chesterfield

Home in Westhampton
Cozy cottage on gorgeous lake
7 beds
1 – 8 May
New place to stay
Guest favourite
Room in Williamsburg
Stay with JillThe arts,
A Place for Peace - suite w/full bath
21 – 26 Apr
4.95 out of 5 average rating, 43 reviews
Guest favourite
Home in Williamsburg
Hilltown Studio
2 beds
28 Apr – 3 May
4.99 out of 5 average rating, 157 reviews
Guest favourite
Home in Chesterfield
High Field Farm
5 beds
29 Apr – 4 May
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Williamsburg
Cute and Cozy Lake Cottage
2 double beds
5 – 10 May
4.9 out of 5 average rating, 20 reviews
Guest favourite
Room in Huntington
Stay with SandraHosting for 7 years,
Cozy room in a nice old home.
28 Apr – 3 May
4.93 out of 5 average rating, 58 reviews
Guest favourite
Room in Worthington
Stay with JimExecutive,
Country Luxury in the Heart of the Berkshires
19 – 24 Apr
5.0 out of 5 average rating, 118 reviews
Guest favourite
Home in Ashfield
Magical, Rural Getaway in the Berkshires
6 beds
28 Apr – 3 May
4.98 out of 5 average rating, 48 reviews
Guest favourite
Home in Ashfield
An 18th century farmhouse
2 beds
19 – 24 Apr
5.0 out of 5 average rating, 7 reviews
Guest favourite
Room in Cummington
Stay with Kathy
Spacious private BR with king bed in Cummington!
20 – 25 Apr
4.92 out of 5 average rating, 26 reviews
Guest favourite
Home in Williamsburg
The Gate House, EV Charger, Farm View
2 beds
24 – 29 Apr
5.0 out of 5 average rating, 68 reviews
Guest favourite
Home in Huntington
Private house on the River
4 beds
29 Apr – 4 May
4.9 out of 5 average rating, 109 reviews
Superhost
Home in Worthington
Morning Side
4 beds
21 – 26 May
Guest favourite
Home in Goshen
Light-filled Lake House in Goshen
3 beds
21 – 28 Apr
5.0 out of 5 average rating, 28 reviews
Superhost
Home in Cummington
Beautiful Secluded Country House
10 beds
24 – 29 Apr
4.89 out of 5 average rating, 99 reviews
Guest favourite
Home in Ashfield
Luxury log style home with views to Mt. Monadnock!
5 beds
21 – 26 Apr
4.92 out of 5 average rating, 38 reviews
Guest favourite
Home in Ashfield
True Shangri-la, Country Retreat
3 beds
21 – 26 Apr
4.95 out of 5 average rating, 57 reviews
Guest favourite
Home in Chester
Riverfront Getaway
2 queen beds
29 Apr – 4 May
4.96 out of 5 average rating, 310 reviews
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