Photo by Wen C.

Chilmark Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 18 - Aug 19
Tomorrow
Aug 19 - Aug 20
This weekend
Aug 22 - Aug 24
Next weekend
Aug 29 - Aug 31

Vacation Rentals in Chilmark

The Club at New Seabury
Private beach nearby, beach bar

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (326)
"A great unique and quiet place, very close to Boston."
The Club at New Seabury
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (176)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters
Sea Mist Resort
Indoor pool, outdoor pool, sun loungers

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (133)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is NT$4,775
NT$5,465 total
includes taxes & fees
Sep 2 - Sep 3
Sea Mist Resort
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (98)
"Great location! Nice property! "
The price is NT$9,419
NT$10,780 total
includes taxes & fees
Aug 19 - Aug 20
Beachside Village Resort
Southcape Resort Mashpee a Ramada by Wyndham
Exterior

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (200)
"Enjoyed our stay."
Southcape Resort Mashpee a Ramada by Wyndham
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chilmark Hotel Reviews

Falmouth Tides

Falmouth Tides

10/10 Excellent
"Absolutely loved our stay, would highly recommend! The views of the ocean are outstanding and you can listen to the ocean waves crash as you sleep Went up to the rooftop deck to watch the gorgeous sunset! Swam out to the docks, lounge chairs with towels, complementary bikes, loved it all! Very friendly staff, 10 out of 10!!!"
carol 1-night trip
Posted 20 hours ago
Falmouth Tides

Frequently asked questions

Can I find vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. Chilmark is known for its beaches and wineries. Make sure you have time to check out the festivals and local tours during your trip.

How many vacation rentals are there in Chilmark?

Choose from 74 Expedia vacation rentals in Chilmark for a memorable vacation.

What’s there to see and do in Chilmark?

Family-friendly attractions include Chilmark Chocolates and Fulling Mill Brook Preserve, whereas Menemsha Beach and Lucy Vincent Beach are a couple of great spots to enjoy the outdoors. While here, Chilmark Town Hall and Chilmark Public Library are other places worth a visit.

What’s a vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.