Photo by Wen C.

Chilmark Holiday Rentals

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Check prices for these dates

Tonight
13 Jun - 14 Jun
Tomorrow
14 Jun - 15 Jun
This weekend
13 Jun - 15 Jun
Next weekend
20 Jun - 22 Jun

Holiday 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, (321)
"A great unique and quiet place, very close to Boston."
The price is S$804
includes taxes & fees
27 Jun - 28 Jun
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, (170)
"The rooms where very clean and well taken care of."
InnSeason Resorts Captain's Quarters
Sea Mist Resort
Indoor pool, outdoor pool, pool loungers

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (124)
"Great place just had another family staying above our room that was very noisy the last night we were there"
The price is S$245
includes taxes & fees
16 Jun - 17 Jun
Sea Mist Resort
Beachside Village Resort
Seasonal outdoor pool

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (93)
"This place is adorable. Very comfortable, clean, cozy and located right across from the beach. Unfortunately they were doing construction in beach parking lot but still enjoyed our stay very much. Will definitely rent there again. "
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, (197)
"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.
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Frequently asked questions

Can I find holiday rentals in Chilmark?

Yes, there are holiday rentals in Chilmark close to Chilmark Chocolates, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals are there in Chilmark?

Choose from 66 Expedia holiday rentals in Chilmark for a memorable holiday.

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 holiday rental in Chilmark like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chilmark. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.