Photo by Wen C.

Chilmark Holiday Rentals

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Holiday Rentals in Chilmark

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (311)
"Tired unit. Primary bath water closet leaked around base. No soap or paper towels. "
The price is AU$252
includes taxes & fees
16 Feb - 17 Feb
The Club at New Seabury

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (74)
"Beautiful home and views"
The price is AU$1,745
includes taxes & fees
7 Feb - 8 Feb
Coastal chic meets French Provençal in this newly renovated oceanfront home.

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (158)
"This is the 4th time I've stayed at an Inn Season resort in Falmouth. There are 3 properties available and they are all quite nice. This visit was at Captains Quarters overlooking Heights Beach. It was a winter weekend with a steady fall of very fine snow. The accommodations are always spot on. It was picturesque and a perfect weekend getaway to relax and unwind. "
InnSeason Resorts Captain's Quarters

Sea Mist Resort by VRI Americas

3.0 star property
8.8 out of 10, Excellent, (113)
"We loved having two full bathrooms and kitchen "
Sea Mist Resort by VRI Americas

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

10.0 out of 10, Exceptional, (22)
"Thank you Thomas and Julie, had a great week, so convenient and Welcoming. "
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

8.6 out of 10, Excellent, (79)
"Great location but the place was dirty. Need a better cleaning service. "
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Large New Seabury Home with Heated Pool and Hot Tub

10.0 out of 10, Exceptional, (39)
"We stayed for a week over the Christmas holidays. The house easily accommodated our group of eight people and one dog. We enjoyed the easy walk to the National Wildlife Refuge and a quick drive for winter beach walks. We enjoyed spending time with a roaring fire and a few dips in the hot tub. Tori was very responsive to the couple of issues that arose. "
Large New Seabury Home with Heated Pool and Hot Tub

Charming Cape Cod get away on Great Pond with porch!

9.8 out of 10, Exceptional, (27)
"Reasonably priced and very comfortable."
Charming Cape Cod get away on Great Pond with porch!

4BD Tranquil Falmouth Breeze Escape w/ Pool

7.6 out of 10, Good, (7)
"Property was clean and Tally was very responsive to questions. Great location close to town and walkable. Very near Shining Sea bike Path"
4BD Tranquil Falmouth Breeze Escape w/ Pool

Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

10.0 out of 10, Exceptional, (56)
"This house is the perfect destination for a group get together. It is an easy walk to the ferry so cars are not needed on the island. we had a great time and are looking forward to our next stay."
Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (190)
"Once again, we enjoyed our family Christmas on the Cape in our favorite area. This house has everything you will need for a comfortable stay. The house is immaculate and completely stocked. The beds are extremely comfortable, there is plenty of room for our entire family to enjoy themselves and Roberta was so easy to communicate with if needed. We will definitely stay here again. "
The price is AU$835
includes taxes & fees
3 Feb - 4 Feb
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

The Beach Estate, Panoramic Ocean Views, 5700 sqft

10.0 out of 10, Exceptional, (5)
"This house is spectacular and we cannot wait to rent again. There’s nothing to complain about except we didn’t rent it longer. "
The price is AU$2,851
includes taxes & fees
12 Feb - 13 Feb
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

9.6 out of 10, Exceptional, (82)
"Wonderful property on the pond. We had a great time. Would rent again. "
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub

10.0 out of 10, Exceptional, (94)
"Great location, even with the weather being awful we were able to utilize some of the amenities. "
Beach front, fenced yard, pet friendly, central air, fire pit, kayaks, hot tub

Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

8.0 out of 10, Very good, (7)
"Cute property in a great location. The neighborhood felt very safe and it was a perfect spot for my family. House was clean and the space was great. "
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights

9.2 out of 10, Wonderful, (26)
"The property was very nice and in a great location. Everything was clean and had plenty of room for us to hang out in. Communication with the owner was excellent and quick. Highly recommend!"
3 Bed 2 Bath - Fully Renovated SS Granite kitchen walk to beach Falmouth heights

Newly Renovated Martha's Vineyard Vacation Rental!

9.8 out of 10, Exceptional, (40)
"This place was great. A quality home with great spaces and nice furnishings. Jenny was incredibly accommodating and responsive. We had a low stress, wonderful time and would certainly come here again. "
The price is AU$995
includes taxes & fees
2 Feb - 3 Feb
Newly Renovated Martha's Vineyard Vacation Rental!

The Costal Corner

2.0 star property
The Costal Corner

Stunning Falmouth Home w/ Deck: Half Mi to Beach

9.6 out of 10, Exceptional, (4)
"Perfect location in Falmouth, eight minute walk to old Silver Beach. Big spacious layout with a lovely yard and back patio."
Stunning Falmouth Home w/ Deck: Half Mi to Beach
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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Other types of properties in Chilmark you may be interested in

Sea Crest Beach Resort

3.5 star property
8.6 out of 10, Excellent, (41)
"Our stay was accomodating for 1 night. Hotel needed work as far as stairways , hallways, doors entering into the rooms looked pretty worn. Most of our guest were located in out building #3. We were in the main building. We asked if we could change rooms to building 3 and were told no rooms available. We found out though in visiting the other guest there was rooms available and 1 of the guest had issues in there room and had to switch to another room in building 3. "
The price is AU$304
includes taxes & fees
5 Feb - 6 Feb
Sea Crest Beach Resort

Harbor View Hotel

5.0 star property
8.8 out of 10, Excellent, (993)
"It doesn’t get any better than this! 🙂"
The price is AU$423
includes taxes & fees
6 Feb - 7 Feb
Harbor View Hotel

Admiralty Inn & Suites - a Red Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (163)
"Good"
The price is AU$189
includes taxes & fees
6 Feb - 7 Feb
Admiralty Inn & Suites - a Red Collection 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.

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.

What are some of the best holiday rentals that Chilmark has to offer?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This holiday home rental outside of Chilmark is located on the beach, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chilmark?

Choose from 70 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.