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Chatham Vacation Rentals(176)

176 Results
$650 - $1,000
per night
2 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(6)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
(12)
$500 - $771
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 7
3 - 7 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
(8)
$200 - $257
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night minimum stay
(7)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 - 7 night minimum stay
(5)
$675 - $829
per night
3 - 7 night minimum stay
  • 7 BR,
  • 4 BA,
  • Sleeps 11
3 - 7 night minimum stay
(10)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
(11)
$180 - $314
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(15)
$300 - $571
per night
2 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 9
2 - 7 night minimum stay
(22)
$180 - $300
per night
3 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(17)
$1,500 - $2,500
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
1 Review
$2,900 - $4,900
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
(6)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 7 night minimum stay
$2,800 - $3,300
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 12
7 night minimum stay
(15)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
(6)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 7 night minimum stay
(8)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(3)
$300 - $371
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night minimum stay
2 Reviews
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(7)
$3,600
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
2 Reviews
$286 - $514
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
$150 - $279
per night
3 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 5
3 - 7 night minimum stay
(5)
$850 - $1,350
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
(7)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
1 - 7 night minimum stay
1 Review
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 2
7 night minimum stay
$130 - $257
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
1 Review
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Recent Chatham Reviews

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

A Great Place to Stay in Chatham

5 of 5
We are long time Chatham vacationers and repeat renters of both the Striper and Bluefish properties for many years. For our family, the cottages are perfectly located to beaches, lighthouse, and town. A lot of trails/paths/quiet roads right here for all of our walkers, bikers, and runners to enjoy. We really like the clean, bright, roomy, open living spaces - a great place to convene and chill out after a long day on the beach or on the water. The owners are very responsive and care about their customers and provide the essentials for your Chatham getaway.
  • Submitted: Nov 10, 2014
  • Stayed: Aug 2014

Great House in Perfect Location

5 of 5
This was the perfect location for our friend's destination wedding at the Chatham Bars Inn. The house is conveniently located walking distance to downtown Chatham, and is even more charming than the pictures convey! The house has been beautifully remodeled and the location right on the pond is so picturesque! We made a big brunch for the groom-to-be the morning of the wedding and were extremely impressed with how stocked the kitchen was with every tool and appliance we possibly needed, plus service for 10 people. Comfy couches and chairs throughout the first floor were perfect for watching movies or sipping coffee. There are also lovely outdoor tables in the front yard and back yard (that we sadly could not use due to rain), but it would be amazing in the summer sunshine. Linda was very communicative before and during our visit, and made the logistics a breeze. Highly recommended!!
  • Submitted: Nov 6, 2014
  • Stayed: Oct 2014