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Search results; Over 1,000 homes in East Chatham

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Cottage in East Chatham
Beautifully Nestled Berkshires Home
4 bedrooms, 5 beds, 2 private bathrooms
13–18 Sept
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4.92 out of 5 average rating, 215 reviews
Guest favourite
Home in Old Chatham
Haddock + Cotter - Chic Farmhouse and Barn w/ Pool
4 bedrooms, 5 beds
14–19 Sept
4.95 out of 5 average rating, 56 reviews
Top guest favourite
Barn in East Chatham
The Loft @ Sweet Pea Farms
1 bedroom, 2 queen beds
14–19 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Old Chatham
Monk's Bunk, Old Chatham
3 bedrooms, 6 beds
14–19 Oct
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Flat in East Chatham
Bennett Abode
1 bedroom, 1 double bed
14–19 Sept
4.96 out of 5 average rating, 191 reviews
Top guest favourite
Home in East Chatham
Secluded Chatham Oasis-Hot Tub+Treehouse+Pets
3 bedrooms, 4 beds
15–20 Sept
5.0 out of 5 average rating, 43 reviews
Top guest favourite
Home in East Chatham
Charming house in historic hamlet
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Guest suite in East Chatham
Private guest suite without the high price.
1 bedroom, 1 king bed
13–18 Sept
4.86 out of 5 average rating, 178 reviews
Guest favourite
Guest house in Canaan
Berkshires Retreat: Treetop Guest House + Gardens
2 bedrooms, 3 beds
20–25 Sept
4.94 out of 5 average rating, 16 reviews
Top guest favourite
Home in Canaan
Relax and Rejuvenate at Fox Hollow Cottage
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Chatham
Writer's Retreat in the Woods
2 bedrooms, 2 queen beds
13–18 Sept
5.0 out of 5 average rating, 48 reviews
Guest favourite
Home in Canaan
The Little Yellow Door
5 bedrooms, 5 beds
1–6 Oct
4.96 out of 5 average rating, 53 reviews
Top guest favourite
Home in Chatham
A unique village home steps to shops, café, nature
4 bedrooms, 4 beds
2–7 Nov
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Old Chatham
The Red House
2 bedrooms, 2 beds
16–21 Nov
4.99 out of 5 average rating, 84 reviews
Top guest favourite
Home in Canaan
Secluded Mountain and Lake View in Canaan, NY
3 bedrooms, 3 beds
28 Sept – 3 Oct
4.95 out of 5 average rating, 44 reviews
Guest favourite
Home in Canaan
Peaceful Berkshire Getaway (A/C, Lake Access)
4 bedrooms, 4 beds
5–10 Oct
4.96 out of 5 average rating, 77 reviews
Top guest favourite
Flat in New Lebanon
Airy apartment at the old boarding house
2 bedrooms, 3 beds
13–18 Sept
4.97 out of 5 average rating, 124 reviews
Top guest favourite
Cabin in East Nassau
Fall Foliage Luxury Cabin & View Autumn Adventures
3 bedrooms, 3 beds
13–18 Sept
4.97 out of 5 average rating, 108 reviews
Top guest favourite
Home in Chatham
spencertown farm house
5 bedrooms, 8 beds
20–25 Sept
4.97 out of 5 average rating, 88 reviews