Photo by Wen C.

Chilmark Holiday Rentals

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Check prices for these dates

Tonight
16 Feb - 17 Feb
Tomorrow
17 Feb - 18 Feb
Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar

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, (311)
"Tired unit. Primary bath water closet leaked around base. No soap or paper towels. "
The price is AU$246
includes taxes & fees
18 Feb - 19 Feb
The Club at New Seabury
Sea Mist Resort
Exterior

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (114)
"We loved having two full bathrooms and kitchen "
Sea Mist Resort
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, (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. "
The price is AU$186
includes taxes & fees
17 Mar - 18 Mar
InnSeason Resorts Captain's Quarters
Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel cot

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

10.0 out of 10, Exceptional, (74)
"Beautiful home and views"
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Dining

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

10.0 out of 10, Exceptional, (34)
"This is the second year in a row that we have stayed in this home. We just love it so much. It has everything you need which makes packing much easier. Owners are great. We hope to stay again."
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Beach nearby, sun-loungers, beach towels

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

10.0 out of 10, Exceptional, (158)
"We had a wonderful, relaxing weekend in this lovely home. Well appointed and comfortable, with everything we needed to cook delicious meals and enjoy our cozy weekend!"
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Outdoor dining

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
Beach nearby

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Interior

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.6 out of 10, Exceptional, (78)
"This apartment was a great location to walk to the shops and restaurants in Oak Bluffs. We typically don't rent 1 bed/1 bath properties but we would rent this one again. It was very large and very clean and comfortable. The morning sun, coming in from over the ocean was beautiful each morning and we could sit out on the balcony with our coffee and people watch. We rented a car, only to explore the rest of the island and that, too, was a convenient walk, less than a block away. All in all,...
The price is AU$848
includes taxes & fees
1 Mar - 2 Mar
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Property grounds

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
Interior

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
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Fridge, microwave, oven, stovetop

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$813
includes taxes & fees
20 Feb - 21 Feb
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
On the beach

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

9.6 out of 10, Exceptional, (83)
"Wish it was warmer lol stayed and it snowed "
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
Outdoor dining

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
Newly Renovated Martha's Vineyard Vacation Rental!
Outdoor dining

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$981
includes taxes & fees
17 Feb - 18 Feb
Newly Renovated Martha's Vineyard Vacation Rental!
4BD Tranquil Falmouth Breeze Escape w/ Pool
Pool

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
Cozy getaway in a central location w/ a full kitchen & furnished deck
Beach

Cozy getaway in a central location w/ a full kitchen & furnished deck

6.8 out of 10, (22)
"You can see by the photos that the home is outdated. However, this home shouldn't even be rented. I rent homes on VBRO all the time and this is my first bad experience. The doors didn't shut, including the two bathrooms. The larger bathroom we tried to avoid. The toliet moved, you could rock back and forth on it if you wanted too. They put a chain lock on the back of the door to hold it shut. A screw in the light switch, to make the switch work. The door in the smaller bathroom didn't shut...
Cozy getaway in a central location w/ a full kitchen & furnished deck
Last minute deal - walk to the beach - 4 bedroom - super cute!
Outdoor dining

Last minute deal - walk to the beach - 4 bedroom - super cute!

9.6 out of 10, Exceptional, (76)
"We loved our 2 day stay in Falmouth. We came up for an October wedding. The VRBo was 3 minutes walking distance from the beautiful beach. There was plenty of room and the house was very clean. We would love to come up again and would definitely recommend staying here! "
Last minute deal - walk to the beach - 4 bedroom - super cute!
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Exterior

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$3,078
includes taxes & fees
4 Mar - 5 Mar
The Beach Estate, Panoramic Ocean Views, 5700 sqft
9-bedroom vacation home near Cape Cod Beaches
9 bedrooms, desk, iron/ironing board, free WiFi

9-bedroom vacation home near Cape Cod Beaches

9.6 out of 10, Exceptional, (17)
"My extended family has been gathering for Thanksgiving every year since the late sixties. In those days, we gathered at Aunt Cacky’s outside of Philadelphia. What I love about this house for Thanksgiving is that it has all the charm and ambience of Cacky’s house but with the amenities of two kitchens with modern appliances. Our hosts could not have been more welcoming, and the house definitely felt like we were home for the holiday. The house is perfect for any large family gathering, especially...
9-bedroom vacation home near Cape Cod Beaches
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
Indoor pool, seasonal outdoor pool

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$303
includes taxes & fees
25 Feb - 26 Feb
Sea Crest Beach Resort
Harbor View Hotel
Shower, designer toiletries, hair dryer, bathrobes

Harbor View Hotel

5.0 star property
8.8 out of 10, Excellent, (994)
"It doesn’t get any better than this! 🙂"
The price is AU$508
includes taxes & fees
17 Feb - 18 Feb
Harbor View Hotel
Admiralty Inn & Suites - a Red Collection Hotel
Lobby

Admiralty Inn & Suites - a Red Collection Hotel

3.0 star property
8.8 out of 10, Excellent, (167)
"The check in staff was very pleasant! Room was larger than expected! Only problem was the room key didn't work great. Needs updating. Otherwise this was a 10/10 place! "
The price is AU$186
includes taxes & fees
23 Feb - 24 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 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 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.