A dock with boats, a small wooden structure, and a forested shoreline.

Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Chilmark vacation rentals

Private beach nearby, beach bar

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (363 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is NT$16,254
NT$18,602 total
includes taxes & fees
Jul 20 - Jul 21
The Club at New Seabury
Cottage (2 Bedrooms) | Interior

4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
The price is NT$7,440
NT$22,044 total
includes taxes & fees
Aug 14 - Aug 15
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
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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Top Chilmark Hotel Reviews

The Harborside Inn

The Harborside Inn

8/10 Good
"The hotel was clean. Great location. Comfortable bed. The only negative was that it had a muggy smell."
Gina 2-night trip
Posted 6 hours ago
The Harborside Inn

Find out more about Chilmark

Search for holiday rentals in Chilmark on Expedia! You can easily find your home rentals, villas, holiday apartments in Chilmark using one of the methods below:

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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 67 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 Edys Island 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.