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Holiday villas in Chatham, NY

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All 52 Rentals in the Chatham Area
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From
€236
Per Night
Chatham
3 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
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From
€90
Per Night
Chatham
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
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The following rentals are within 25 kilometers of Chatham, New York.

From
€192
Per Night
Valatie
3 Bedrooms, 3 Bathrooms, Sleeps 5
9 photos Details
Reviews (3) Make Enquiry
From
€236
Per Night
East Chatham
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
9 photos Details
Reviews (1) Make Enquiry
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4 of 5 stars Reviewed 10 September 2014
Stunningly beautiful house. Huge windows framing forest views outside. Beautiful, beautiful woodwork, floors, dining table and built in shelves, bedframes and lovely walk in...
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From
€197
Per Night
Great Barrington, MA
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
10 photos Details
Reviews (2) Make Enquiry
5 of 5 stars Reviewed 20 May 2013
This was a perfect weekend for us. I am very picking when choosing a cabin rental because I want it to be "just right--" to fit into all of my ideal visions of the quintessential...
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From
€335
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 13
Booking
18 photos Details
Reviews (1) Make Enquiry
From
€87
Per Night
Richmond, MA
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
11 photos Details
Reviews (4) Make Enquiry
From
€118
Per Night
Hillsdale
4 Bedrooms, 3 Bathrooms, Sleeps 7
Booking
45 photos Details
Reviews (1) Make Enquiry
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From
€126
Per Night
North Egremont, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
35 photos Details
Reviews (5) Make Enquiry
5 of 5 stars Reviewed 12 September 2014
I had a wonderful stay! The property is gorgeous and serene. The suite is clean, very nicely decorated and private. Absolutely lovely!
5 of 5 stars Reviewed 4 September 2014
Lovely haven in the bucolic Berkshire countryside . Our suite had everything we could want- privacy, beautiful restful decor, comfort , all in a gorgeous setting. Short drive to...
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From
€146
Per Night
Alford, MA
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
12 photos Details
Reviews (3) Make Enquiry
From
€118
Per Night
Ghent
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
11 photos Details
Reviews (1) Make Enquiry
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5 of 5 stars Reviewed 6 August 2013
This was the perfect location for a base camp from which to explore the Hudson River Valley area. We took in a Tanglewood concert (40-minute drive) and explored the backroads full...
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From
€99
Per Night
West Stockbridge, MA
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
6 photos Details
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5 of 5 stars Reviewed 18 December 2013
We stayed at this home in Housatonic, which is part of Great Barrington, the Smithsonian pic for best small town in the USA. I hope you all don't however as one of the best...
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From
€1,577
Per Week
Hudson
3 Bedrooms, 2 Bathrooms, Sleeps 8
17 photos Details
Reviews (2) Make Enquiry
From
€236
Per Night
Athens
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
23 photos Details
Reviews (4) Make Enquiry
5 of 5 stars Reviewed 1 September 2014
This home is located on a quiet cove on Sleepy Hollow Lake. It is immaculate and the amenities are similar to those found in an expensive bed and breakfast. We arrived to find...
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From
€197
Per Night
West Stockbridge, MA
5 Bedrooms, 2 Bathrooms, Sleeps 12
Bookings
12 photos Details
Reviews (7) Make Enquiry
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5 of 5 stars Reviewed 31 August 2014
We were a group nine. We found the house to have a rustic charm complete with hardwood floors and exposed beams in the walls and ceilings. We tended to congregate in the living...
5 of 5 stars Reviewed 30 August 2014
My brother and sister and I, along with our significant others, gathered together here for a week to enjoy the Berkshires. The house suited our needs much better than other...
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From
€197
Per Night
Austerlitz
4 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
12 photos Details
Reviews (3) Make Enquiry
From
€197
Per Night
West Stockbridge, MA
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
14 photos Details
Reviews (4) Make Enquiry
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5 of 5 stars Reviewed 25 August 2014
We were excited to get away from NYC and stay in the Berkshires! It was a wonderful stay at this home! So spacious, comfortable, lots of thoughtful gestures for our stay! We...
5 of 5 stars Reviewed 25 August 2014
Four of us stayed for a week, mostly cooking in, aided by a well-equipped kitchen and outdoor grill, as well as very comfortable dining areas - inside and out. Nice yard with...
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From
€154
Per Night
Great Barrington, MA
1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
10 photos Details
Reviews (9) Make Enquiry
5 of 5 stars Reviewed 17 August 2014
We stayed at the cottage for three days, and it was just as lovely as advertised. The space is perfect for a couple, with a comfortable queen bed and well-equipped kitchen...
5 of 5 stars Reviewed 22 July 2014
My wife and I were extremely lucky to find Efrem and Frederica's cottage in The Berkshires. We really enjoyed the beautiful and relaxing view that their backyard had to offer! The...
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From
€256
Per Night
Great Barrington, MA
5 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
27 photos Details
Reviews (1) Make Enquiry
3 of 5 stars Reviewed 11 September 2014
This is a very large house, more than adequate in size for a group of ten people. It has a big yard and a spectacular view of the mountains, especially from an upstairs window...
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From
€276
Per Night
Austerlitz
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details
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From
€138
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
30 photos Details
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From
€99
Per Night
Valatie
4 Bedrooms, 2 Bathrooms, Sleeps 6
1 photo Details
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From
€315
Per Night
Hudson
3 Bedrooms, 2 Bathrooms, Sleeps 6
9 photos Details
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From
€236
Per Night
Great Barrington, MA
4 Bedrooms, 2 Bathrooms, Sleeps 9
Booking
11 photos Details
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From
€3,547
Per Week
Great Barrington, MA
6 Bedrooms, 6 Bathrooms, Sleeps 12
25 photos Details
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From
€276
Per Night
Athens
4 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
34 photos Details
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From
€276
Per Night
Great Barrington, MA
5 Bedrooms, 3 Bathrooms, Sleeps 11
9 photos Details
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From
€414
Per Night
Richmond, MA
3 Bedrooms, 3 Bathrooms, Sleeps 6
20 photos Details
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From
€158
Per Night
Great Barrington, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
15 photos Details
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From
€197
Per Night
Columbiaville
2 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
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From
€79
Per Night
Hillsdale
2 Bedrooms, 1 Bathroom, Sleeps 3
10 photos Details
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From
€158
Per Night
Great Barrington, MA
2 Bedrooms, 2 Bathrooms, Sleeps 4
10 photos Details
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From
€158
Per Night
Hudson
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
7 photos Details
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From
€158
Per Night
Great Barrington, MA
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
10 photos Details
Make Enquiry
From
€374
Per Night
Great Barrington, MA
4 Bedrooms, 6 Bathrooms, Sleeps 12
22 photos Details
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From
€39
Per Night
Hudson
2 Bedrooms, 1 Bathroom, Sleeps 11
20 photos Details
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From
€236
Per Night
Great Barrington, MA
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
23 photos Details
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From
€118
Per Night
Craryville
2 Bedrooms, 3 Bathrooms, Sleeps 6
6 photos Details
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From
€79
Per Night
Hillsdale
3 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Reviews (4) Make Enquiry
From
€311
Per Night
Hudson
4 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
Reviews (10) Make Enquiry
5 of 5 stars Reviewed 29 May 2014
This house is impeccable ! The location is within walking distance to all of the great restaurants and antique shops on Warren St. There was so much thought put into the...
5 of 5 stars Reviewed 19 June 2013
This house is even more beautiful than the pictures. It feels like your own home, just a more deluxe, stylish and comfortable version. Juan, the owner made everything very easy...
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From
€453
Per Night
Great Barrington, MA
4 Bedrooms, 3 Bathrooms, Sleeps 10
33 photos Details
Reviews (3) Make Enquiry
From
€110
Per Night
Richmond, MA
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
7 photos Details
Reviews (1) Make Enquiry
2 of 5 stars Reviewed 11 September 2014
I recently rented this vacation rental with a couple friends to go to Tanglewood and Kripalu. While the house has a lot of potential, it has been very poorly maintained. The...
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From
€118
Per Night
Hillsdale
3 Bedrooms, 3 Bathrooms, Sleeps 8
8 photos Details
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From
€300
Per Night
Hudson
3 Bedrooms, 2 Bathrooms, Sleeps 6
8 photos Details
Make Enquiry
From
€79
Per Night
Richmond, MA
2 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Make Enquiry
From
€197
Per Night
Great Barrington, MA
3 Bedrooms, 2 Bathrooms, Sleeps 8
19 photos Details
Make Enquiry
From
€197
Per Night
Richmond, MA
3 Bedrooms, 2 Bathrooms, Sleeps 8
10 photos Details
Make Enquiry
From
€125
Per Night
Great Barrington, MA
5 Bedrooms, 5 Bathrooms, Sleeps 10
20 photos Details
Make Enquiry
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Suitability

  • Wheelchair access (1)
  • Elder access (18)
  • Suitable for children (35)
  • Pet friendly (14)
  • Smoking allowed (0)

Amenities

  • Internet (42)
  • Other outdoor space (42)
  • Grill (37)
  • Parking (36)
  • Washer/Dryer (34)
  • View all amenities
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