Photo by Wen C.

Chilmark Holiday Rentals

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Check prices for these dates

Tonight
8 Aug - 9 Aug
Tomorrow
9 Aug - 10 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Holiday Rentals in Chilmark

The Club at New Seabury
Enjoy beachside cabanas and umbrellas, a covered pavilion, and scenic views amidst lush greenery.

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (325)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
The Club at New Seabury
InnSeason Resorts Captain's Quarters
Enjoy a serene beach experience with a gentle slope leading to the calm sea.

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (175)
"Just a quick weekend away. Great location for beach lovers. Also excellent retaurants "
InnSeason Resorts Captain's Quarters
Beachside Village Resort
Enjoy a serene retreat with a pool and lush surroundings.

Beachside Village Resort

3.0 star property
9.4 out of 10, Exceptional, (96)
"Great location! Nice property! "
The price is S$543
includes taxes & fees
12 Aug - 13 Aug
Beachside Village Resort
Sea Mist Resort
Relax by the pool, surrounded by comfortable lounge chairs.

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 S$234
includes taxes & fees
2 Sept - 3 Sept
Sea Mist Resort
Southcape Resort Mashpee a Ramada by Wyndham
Houses with brick exteriors and white trim stand amidst well-manicured lawns and trees.

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.
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Top Chilmark Hotel Reviews

Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven

10/10 Excellent
"It’s just perfect for me. It’s close to my family when I visit from New York and it’s a good place to call it the night. The staff is friendly, the rooms are great, and the breakfast is excellent. Even better, our dog Tonio is welcome. "
Jose 2-night trip
Posted 2 days ago
Hampton Inn by Hilton New Bedford/Fairhaven

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 74 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.