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Compare 156 Cottages in Chilmark with updated reviews, rates, and availability.

Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
Private condo in Maushop. Steps to beach, ocean, Popponesset Inn and Marketplace
9.6 out of 10, Exceptional, (64)

5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
5-Stars, Exceptional, 2 bedrooms, 1.5 baths, with magnificent views.
10.0 out of 10, Exceptional, (20)

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach
6.2 out of 10, (17)

Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
Popponesset-Beach Cottage, 2 bedrooms, 1.5 baths, outdoor shower
10.0 out of 10, Exceptional, (23)

Oceanside Cottage with Private Beach
Oceanside Cottage with Private Beach
10.0 out of 10, Exceptional, (3)

2-bdrm Cottage | Close to Everything | Pet Friendly
2-bdrm Cottage | Close to Everything | Pet Friendly
9.8 out of 10, Exceptional, (9)

★The Islander | Steps From Water, Fire Pit, AC★
★The Islander | Steps From Water, Fire Pit, AC★
10.0 out of 10, Exceptional, (45)

Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability
Chappaquiddick, Cozy 2 Bedroom, Spring and Fall Derby availability
10.0 out of 10, Exceptional, (25)
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

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
8.8 out of 10, Excellent, (9)

InnSeason Resorts Captain's Quarters
InnSeason Resorts Captain's Quarters
9.8 out of 10, Exceptional, (165)
The price is SAR 559
SAR 640 total
includes taxes & fees
14 Apr - 15 Apr

The Club at New Seabury
The Club at New Seabury
9.0 out of 10, Wonderful, (315)
The price is SAR 757
SAR 866 total
includes taxes & fees
29 Apr - 30 Apr
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

Admiralty Inn & Suites - a Red Collection Hotel
5/5 Excellent
Will definetly be back for return visit!!!!
"Fantastic stay and the property was better than i expected... But indoor pool could use some reconfiguring... Preferably a deep end added..."
A verified traveler stayed at Admiralty Inn & Suites - a Red Collection Hotel
Posted 1 day ago