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Chatham Vacation Rentals with parking included(20)

20 Results
  • 8 BR,
  • 5 BA,
  • Sleeps 14
1 - 2 night min stay
(7)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
7 night min stay
$1,000 - $1,514
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night min stay
2 Reviews
$800 - $900
per night
3 night min stay
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 8
3 night min stay
(15)
$229 - $350
per night
2 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
1 Review
$214
per night
6 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 9
6 night min stay
(12)
$165 - $170
per night
2 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 night min stay
(4)
  • 6 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night min stay
(4)
  • 3 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(7)
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
$3,500 - $4,165
per week
7 - 30 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 - 30 night min stay
(6)
  • 4 BR,
  • 5 BA,
  • Sleeps 6
2 - 9 night min stay
$167 - $197
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 - 7 night min stay
(12)
$250
per night
3 - 5 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 - 5 night min stay
(7)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night min stay
(8)
5 more choices from the HomeAway Network
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 night min stay
(7)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 5 night min stay
2 Reviews
  • 1 BR,
  • 1 BA,
  • Sleeps 4
7 night min stay
$550 - $600
per night
2 - 4 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night min stay
2 Reviews
$1,575
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
7 night min stay
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Recent Chatham Reviews

Perfect Getaway for Cousins Club Weekend!

5 of 5
We were in search of a large house that could accommodate many families for our cousins club weekend and the Berkshire Country Estate was the perfect find! Plenty of room for families to have their own space but also convene together for dining and game playing. We were all very comfortable in this beautiful, charming home and the owners were a pleasure to deal with and very welcoming. The house is well equipped with cooking utensils and a grill so it was easy to eat in as a family. Also, the game room was a big plus for the kids (they loved the air hockey and pin ball machine) and the outside swing set and basketball hoop were a plus and we all enjoyed ping pong in the barn. We even had a family kick ball game on the large yard. I know there are plenty of sightseeing opportunities close to this property but the house was so great, we never left for the weekend! Thank you for a memorable weekend and we look forward to returning:)
  • Submitted: Nov 13, 2014
  • Stayed: May 2014

Peace All - Around

5 of 5
We are from the Hills of Tennessee, so when you think of New York, you think BIG CITIES. What a wonderful surprise awaited us in Chatham , New York. This beautiful home surrounded by Quiet and nature was heaven sent. After a 13 hour drive this by far the most relaxing, comfortable trip we have ever been on. From the first time we talked to the owner Ms. Virginia to leaving the property we felt at home. The location was great. We were in close driving distance to watch our son play ball in Pittsfield Mass. to driving to towns of so much history and then on to the outlet Malls. Our favorite place was the deck of the home and our son and some of the players enjoyed the fire pit. The house was roomy with games, TV, and books to read. The bedrooms and showers were very comfortable and relaxing. The kitchen was great to fix meals in as well as the outdoor grill. We highly recommend this home and when heading north of the Mason Dixon we hope to stay again. Book Early!!!!
  • Submitted: Aug 19, 2014
  • Stayed: Jul 2014

Perfect Upstate Getaway!

5 of 5
We enjoyed a perfect long weekend upstate at this beautiful, thoughtfully prepared house. This was a perfect getaway for us given the house felt remote and secluded but offered all the amenities, and more, that we normally expect. The house was in great condition and was constructed in a way that was perfect for us in that the three sets of two bedrooms were on different floors and all were tucked away from the main living space which was great for us given we have small children. We were able to hang out both early and late w/out bothering the kids. The house was well stocked and had literally everything we needed. We also enjoyed trips to the country store and had a number of nice meals downtown. I highly recommend this property and hope to visit again.
  • Submitted: Jul 16, 2014
  • Stayed: Jun 2014