Chilmark Vacation Rentals

Compare 7 vacation rentals.
USA > Massachusetts > Chilmark

Make Chilmark your next getaway

Kick back on island time with Chilmark vacation rentals. Here, you’ll find a quiet residential town that includes nearby Nomans Land Island and Martha’s Vineyard must-sees. Find the right haven for your rest and relaxation amongst these ocean-view hideaways. 

Explore Chilmark house rentals, and more


House rentals

View 7 House rentals

Chilmark vacation rentals for every getaway

Dog-friendly Hot tub Internet
Lady Slipper Hill
4 Bedroom | 2.5 Bath | Sleeps 8

Lady Slipper Hill - Chilmark, MA

$433 avg / night
The Eliot Noyes
4 Bedroom | 2 Bath | Sleeps 8

The Eliot Noyes - Chilmark, MA

$843 avg / night
Chilmark Beauty
4 Bedroom | 2 Bath | Sleeps 8

Chilmark Beauty - Chilmark, MA

$489 avg / night
Hillside Oak
4 Bedroom | 4 Bath | Sleeps 8

Hillside Oak - Chilmark, MA

$558 avg / night
Vineyard Vacation Cottage
3 Bedroom | 1.5 Bath | Sleeps 6

Vineyard Vacation Cottage - Chilmark, MA

$428 avg / night

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Recent Chilmark vacation rental reviews

We enjoyed this beautiful home. It's well taken care of, spotless upon arrival, extremely comfortable beds, fully stocked kitchen (if you love to cook) and full of natural light. The location is very private and quiet.
Ann Marie I. | Mar 2024
We loved the location, very secluded, nice area of island. The house felt like home, yummy towels, very comfy beds, relaxing tub, great open living space.
Kimberly B. | Nov 2023
The views, the vibe, the layout, the seclusion, the design, the peace. Nature.
Peter M. | Nov 2023
Chilmark vacation rental FAQ

Yes, 52 of our Chilmark homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 156 of our Chilmark vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >

Some of the most popular amenities in our Chilmark vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Chilmark team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Chilmark, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning

Explore our Chilmark, MA, vacation rentals

Soothing ocean views and warm-weather bliss await with Chilmark vacation rentals. You'll find out soon enough why so many travelers keep Martha’s Vineyard in their sights when dreaming up beach getaways. Head to this bucolic wonder and feel your worries wash away in the sand. 

Whether a family vacation or a romantic getaway, Chilmark offers the ideal scenic backdrop to new memories made along the coast. If you’ve ever wanted to spend time along Cape Cod without the bustle of crowds, this is the perfect place. Stroll by the scenic small ponds, relax amid the wildflowers at Cedar Neck Tree Sanctuary, or head into Tisbury for fine dining options and fresh seafood eateries.

Things to do in Chilmark, MA

There is so much to discover on your next trip to the shore. From your home back in Chilmark, you can easily explore all that Martha’s Vineyard, Cape Cod, and Nantucket have to offer. 

Day Trips from Chilmark

While Chilmark is a great place to explore, you could spend plenty of time venturing out of town and seeing all the other great spots on the Vineyard. West Tisbury has a 60-acre Polly Hill Arboretum that’s well worth a visit, as well as a collection of markets and cafes. Vineyard Haven is known for the Long Point Wildlife Refuge, as well as a number of mom-and-pop shops. Edgartown has the peaceful Cape Pogue Wildlife Refuge and the Felix Neck Wildlife Sanctuary. Ride the country's oldest carousel in Oaks Bluff or visit the historic East Chop Lighthouse. 

Natural beauty and tranquility blend together in lovely Chilmark. Book a Chilmark vacation rental today and take advantage of peaceful coastal living.