Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Cottages
Estates
Farmhouses
Homes
Studios
Townhomes
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Hotels
Lodges
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chatham Vacation Rentals(130)

130 Results
$650 - $750
per night
2 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(6)
$650 - $829
per night
3 - 7 night minimum stay
  • 7 BR,
  • 4 BA,
  • Sleeps 11
3 - 7 night minimum stay
(10)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
3 - 7 night minimum stay
(12)
$450 - $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)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 - 7 night minimum stay
(5)
$200 - $257
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
3 - 7 night minimum stay
(7)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night minimum stay
(11)
$300 - $571
per night
2 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 9
2 - 7 night minimum stay
(21)
$180 - $300
per night
3 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(17)
$180 - $314
per night
3 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
3 - 7 night minimum stay
(14)
$1,500 - $2,500
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
1 Review
$2,900 - $5,500
per week
7 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
(6)
$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 - 14 night minimum stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
7 night minimum stay
(7)
$286 - $343
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 6
2 - 7 night minimum stay
(6)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
2 Reviews
$300 - $436
per night
2 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
2 - 7 night minimum stay
2 Reviews
$3,600
per week
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night minimum stay
2 Reviews
$850 - $1,350
per week
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night minimum stay
(6)
$200 - $279
per night
3 - 7 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 5
3 - 7 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(7)
$2,000
per week
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 5
2 - 7 night minimum stay
(10)
$250 - $328
per night
3 - 7 night minimum stay
  • 3 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(9)
$171 - $175
per night
1 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
1 - 7 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(4)
Advertisement
 

Recent Chatham Reviews

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

Wonderful location, peaceful and comfortable.

5 of 5
We had a most enjoyable and peaceful stay at the Windmill Cottage. The location is fabulous – a beautiful view, especially at dawn! It’s quiet and peaceful, yet all the amenities are close by. The living room, dining room, and patio are very spacious, and the kitchen is very well equipped to prepare wonderful fresh seafood meals. If we return to Cape Cod, we will definitely be staying here again.
  • Submitted: Oct 24, 2014
  • Stayed: Sep 2014