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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)
The price is SAR 1,497
SAR 3,357 total
includes taxes & fees
21 May - 22 May

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, (47)

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, (168)

The Club at New Seabury
The Club at New Seabury
9.0 out of 10, Wonderful, (315)
The price is SAR 709
SAR 811 total
includes taxes & fees
1 May - 2 May
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

Inn on the Square
5/5 Excellent
"Beautiful and well kept property and indoor pool. "
A verified traveler stayed at Inn on the Square
Posted 20 hours ago