Chilmark Vacations

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Find the Best Chilmark Vacation Packages

Chilmark Beach Vacation

Whether you're traveling solo or with the whole gang, it'll be easy to find rest and relaxation on your Chilmark vacation. Search around for shiny rocks and shells or simply sit and watch the sunset. Whatever you choose to do, your trip to Chilmark will certainly be memorable. Lucy Vincent Beach, located 2 kilometers from the town center, is perfect for those after convenience. Many visitors also lock in Chilmark vacation packages closer to Menemsha Beach, another great nearby option.

Chilmark Hotel Deals

Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is ￥11,479 per night from Dec 11 to Dec 12
￥11,479
￥13,139 total
Dec 11 - Dec 12
includes taxes & fees
8.4/10 Very Good! (149 reviews)
Clean room

Reviewed on Nov 20, 2025

Iris Hotel Cape Cod
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
The price is ￥15,833 per night from Dec 28 to Dec 29
￥15,833
￥21,245 total
Dec 28 - Dec 29
includes taxes & fees
7.8/10 Good! (1,003 reviews)
Clean room. Nice staff, convenient location. We enjoyed a drink and live music at the restaurant attached.

Reviewed on Nov 16, 2025

Falmouth Inn
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
23 Kelly Street Edgartown MA
8.8/10 Excellent! (1,006 reviews)
Amazing!

Reviewed on Nov 27, 2025

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Faraway Martha's Vineyard
See all 2,190 properties in Chilmark
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.

What to do in Chilmark

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

￥7,869
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

￥7,869
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Chilmark
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.