Photo by Wen C.

Chilmark Holiday Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Chilmark

The Club at New Seabury
Seasonal outdoor pool, pool cabanas (surcharge), pool umbrellas
The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (304)
"will definitely go back again .. awesome place! "
The price is S$227
includes taxes & fees
25 Nov - 26 Nov
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, (154)
"Very clean property. Beach just across street. Great views."
InnSeason Resorts Captain's Quarters
Beachside Village Resort by VRI Americas
Beach nearby
Beachside Village Resort by VRI Americas
3.0 star property
9.2 out of 10, Wonderful, (86)
"A very nice place and wonderful location. You can see sunrise from this property. Staff are nice and friendly. A great experience!"
Beachside Village Resort by VRI Americas
Sea Mist Resort by VRI Americas
Exterior
Sea Mist Resort by VRI Americas
3.0 star property
8.8 out of 10, Excellent, (111)
"We loved having two full bathrooms and kitchen "
Sea Mist Resort by VRI Americas
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.
Don't see what you're looking for?
See all available properties in Chilmark
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Chilmark you may be interested in

Mansion House Inn And Spa
View from property
Mansion House Inn And Spa
3.5 star property
9.4 out of 10, Exceptional, (1021)
"Very lovely hotel in a great area."
The price is S$241
includes taxes & fees
24 Nov - 25 Nov
Mansion House Inn And Spa
Sea Crest Beach Resort
Indoor pool, seasonal outdoor pool
Sea Crest Beach Resort
3.5 star property
7.6 out of 10, Good, (29)
"We complained about the first room we were given in that there were two flight's of stairs to climb(and it was teeny tiny. They accommodated us with a nicer room, with a view. The only weiired thing was there was no microwave? Fridge/freezer, coffee maker but no micro. This seemed unusual for us as wve stayed in many hotel rooms and a microwave is usually standard. Huge TV though."
The price is S$283
includes taxes & fees
1 Dec - 2 Dec
Sea Crest Beach Resort
Holiday Inn Cape Cod-Falmouth, an IHG Hotel
Garden
Holiday Inn Cape Cod-Falmouth, an IHG Hotel
3.0 star property
7.6 out of 10, Good, (764)
"Nothing else to say."
The price is S$139
includes taxes & fees
24 Nov - 25 Nov
Holiday Inn Cape Cod-Falmouth, an IHG Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 69 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 Lucy Vincent Beach and Menemsha 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.