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Compare 716 Vacation Homes in Chilmark with updated reviews, rates, and availability.
![Access to pond with dock and paddle boat!](https://images.trvl-media.com/lodging/89000000/88110000/88105300/88105289/66918e87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
10.0 out of 10, Exceptional, (22)
![Exterior](https://images.trvl-media.com/lodging/39000000/38310000/38302000/38301922/ccbfe37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Historic Oak Bluffs home, short walk to town, beach, and harbor.
9.6 out of 10, Exceptional, (28)
![Exterior](https://images.trvl-media.com/lodging/110000000/109530000/109523100/109523034/3c0bd8e6_edited_7de5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Gorgeous Spacious Victorian Cape Code Beach View Retreat
Gorgeous Spacious Victorian Cape Code Beach View Retreat
![The perfect backyard for summer fun. A brand new hot tub and pool await.](https://images.trvl-media.com/lodging/43000000/42060000/42052300/42052227/8af2c612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Large New Seabury Home with Heated Pool and Hot Tub
Large New Seabury Home with Heated Pool and Hot Tub
10.0 out of 10, Exceptional, (39)
![Exterior](https://images.trvl-media.com/lodging/50000000/49040000/49037700/49037659/6365bc78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
10.0 out of 10, Exceptional, (56)
![Cathedral Cape located in the highly desirable Katama area of Edgartown](https://images.trvl-media.com/lodging/34000000/33420000/33415200/33415195/0cc33c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
10.0 out of 10, Exceptional, (89)
![2 Crafts Field Way, Edgartown
(outside shower)
(9 beach chairs in shed)](https://images.trvl-media.com/lodging/35000000/34530000/34520100/34520062/4041c813.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Martha’s Vineyard 4BR Home-Katama Edgartown South Beach Area-open Mem Day wknd
Martha’s Vineyard 4BR Home-Katama Edgartown South Beach Area-open Mem Day wknd
9.8 out of 10, Exceptional, (49)
![](https://images.trvl-media.com/lodging/102000000/101770000/101760300/101760261/d57a9986.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
7.4 out of 10, Good, (3)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chilmark
![Outdoor pool](https://images.trvl-media.com/lodging/12000000/11630000/11621700/11621632/58b715f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
The Club at New Seabury
The Club at New Seabury
9.0 out of 10, Wonderful, (311)
The price is AED 502
AED 574 total
includes taxes & fees
23 Feb - 24 Feb
![Exterior](https://images.trvl-media.com/lodging/67000000/66700000/66698300/66698285/7b1afadb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (74)
![Aerial view](https://images.trvl-media.com/lodging/2000000/1160000/1154100/1154022/8226918d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)
InnSeason Resorts Captain's Quarters
InnSeason Resorts Captain's Quarters
9.8 out of 10, Exceptional, (158)
The price is AED 380
AED 435 total
includes taxes & fees
16 Mar - 17 Mar
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Recent reviews of Chilmark hotels
Recent reviews of Chilmark hotels
![Mansion House Inn And Spa](http://images.trvl-media.com/lodging/3000000/2190000/2182100/2182094/e86ce24b_y.jpg)
Mansion House Inn And Spa
5/5 Excellent
"Close to the ferry and shops"
A verified traveler stayed at Mansion House Inn And Spa
Posted 3 days ago