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Your Chilmark Vacation
With a reputation for its unspoiled nature and spectacular views, Chilmark is a perfect getaway destination. Book one of our Chilmark vacation packages and enjoy all that this fascinating city has to offer. If a sightseeing tour is on the agenda during your trip to Chilmark, look around major attractions like Aquinnah Cliffs, Gay Head Lighthouse and Menemsha Beach. No matter your travel plans or the size of your budget, putting together the ultimate tailored Chilmark vacation is a cinch with Expedia.
The Latest Chilmark vacation packages

Summercamp
Reviewed on Jul 30, 2025

The Franklin Hotel Martha's Vineyard
Reviewed on Jul 19, 2025


Faraway Martha's Vineyard
Reviewed on Jul 9, 2025

The Richard, The Edgartown Collection
Reviewed on Jul 31, 2025
Discover the most popular places to visit in Chilmark
Menemsha Beach
Why not spend a carefree afternoon at Menemsha Beach during your travels in Chilmark? Take in the festivals and sunsets in the area.
Lucy Vincent Beach
If a restful vacation is part of your travel plans, Lucy Vincent Beach might be the perfect place to seek out during your trip to Chilmark. Take in the festivals and sunsets in the area.
Chilmark Chocolates
Enjoy an outing to Chilmark Chocolates during your stay in Chilmark. While in this walkable area, you can savor the wineries.
What to do in Chilmark

Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts: Smartphone-Based Audio Tour Bundle

New Budget Friendly Shared 4 hour African American Heritage Tour
Chilmark Hotel Deals

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.
Reviewed on Jul 5, 2025

Iris Hotel Cape Cod
Reviewed on Jul 13, 2025

Vineyard Harbor Motel - Private Beach
Reviewed on Jul 30, 2025
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 1 mile (2 km) 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.
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