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Chatham Vacation Rentals with Online Payment(199)

199 Results
$650 - $1,000
per night
2 - 7 night min stay
  • 5 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night min stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night min stay
(12)
$500 - $771
per night
3 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
3 - 7 night min stay
(5)
$200 - $257
per night
3 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night min stay
(8)
$2,800 - $3,300
per week
7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 12
7 night min stay
(15)
$899 - $1,299
per night
4 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 night min stay
(4)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 - 7 night min stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night min stay
(8)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night min stay
(11)
$225 - $314
per night
3 - 7 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night min stay
(16)
$675 - $829
per night
3 - 7 night min stay
  • 7 BR,
  • 4 BA,
  • Sleeps 11
3 - 7 night min stay
(10)
$350 - $571
per night
2 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 9
2 - 7 night min stay
(22)
$225 - $300
per night
3 - 7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night min stay
(17)
$290 - $880
per night
2 - 3 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 11
2 - 3 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 night min stay
1 Review
$1,500 - $2,500
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
1 Review
$195 - $475
per night
2 - 3 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 - 3 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night min stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
3 - 4 night min stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night min stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night min stay
(8)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
(7)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
(3)
$300 - $371
per night
3 - 7 night min stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night min stay
2 Reviews
$1,200 - $2,400
per week
7 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
7 night min stay
$1,900 - $2,900
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night min stay
$3,000 - $3,600
per week
7 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
2 Reviews
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night min stay
2 Reviews
$200 - $279
per night
3 - 7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 5
3 - 7 night min stay
(5)
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Recent Chatham Reviews

Perfect relaxing get away!

5 of 5
Charming and perfectly situated vacation home in the heart of the village, with restorative views of the water! The owners are gracious and have every thoughtful amenity in their lovely home! We will be back!
  • Submitted: Apr 26, 2015
  • Stayed: Apr 2015

Hidden Gem

5 of 5
We stayed at this at this cottage in June 2014. We loved how peaceful and quiet the location was and especially loved the dark night sky as you are literally on the edge of the country in this location. The stars on the back deck were just stunning I took this picture of the milkyway off the back deck. https://www.flickr.com/photos/lisa568/14490888541/ . Its a short walk to the Chatham lighthouse - https://www.flickr.com/photos/lisa568/14629949003/ and beautiful beaches. Great spot for running and fishing also as it is near the nature preserve. Walter is great also! :)
  • Submitted: Apr 1, 2015
  • Stayed: Jun 2014

Great time at the beautiful Windmill!!!

5 of 5
Great Vacation is if you stay at nice, quiet, relaxing place with a beautiful views! That is exactly what we had in the small Windmill house. We planned our vacation last minute and were very fortunes to be able book this rustic house. It located in residential quiet neighborhood about 10 min from downtown Chatham. We asked for dates from Saturday to Sunday which is unusual dates for house rental. But the owner Tsedale was very accommodating because it was at the end of the season. She gave us all necessary information about house and some links for to do activities. When we arrived we just loved the location and house with Beautiful view on the Crown bay. We rented a kayak and discover small islands in the area. Private beach, swing chair under the tree. I did so many beautiful pictures. Every night we would have fire in the fire pit and enjoy beautiful stars, glass of wine, marshmallows and chocolate made our nights unforgettable. We would love to come back for another vacation. Defiantly recommend. Charles & Natalya
  • Submitted: Jan 24, 2015
  • Stayed: Aug 2014