Photo by Wen C.

Chilmark Vacation Rentals

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Vacation Rentals in Chilmark

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

8.8 out of 10, Excellent, (9)
"Private with beach access minutes away."
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (165)
"Beautiful property. Lots of amenities. Excellent appliances. Great location. View of the ocean & pool. Peaceful."
The price is CA $220
CA $252 total
includes taxes & fees
Apr 27 - Apr 28
InnSeason Resorts Captain's Quarters

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (315)
"Perfect little cottage!"
The price is CA $279
CA $319 total
includes taxes & fees
May 15 - May 16
The Club at New Seabury

Sea Mist Resort

3.0 star property
8.8 out of 10, Excellent, (117)
"Cute and relaxing, just enough on property to do if you have little ones or want to relax with some options!"
Sea Mist Resort

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

10.0 out of 10, Exceptional, (77)
"Great stay! "
The price is CA $967
CA $1,980 total
includes taxes & fees
May 18 - May 19
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Summer home with expansive deck & wonderful location for beachgoers

6.6 out of 10, (17)
"The house was very cute, it was calming and peaceful and the view on the porch was just magnificent. I would definitely come back again!"
Summer home with expansive deck & wonderful location for beachgoers

Southcape Resort Mashpee a Ramada by Wyndham

3.0 star property
8.6 out of 10, Excellent, (193)
"Everything was good quality "
Southcape Resort Mashpee a Ramada by Wyndham

Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

8.8 out of 10, Excellent, (57)
"Good location. Would stay again."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

6.2 out of 10, (17)
"Great location and private beach access. Charming enclave perfect for our weekend getaway."
Cape Cod cottage with patio - near golf, 100 yards to private Mashpee Beach

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

10.0 out of 10, Exceptional, (22)
"Good location, pretty spot on pond. Nice deck plenty of room for family of 12"
The price is CA $208
CA $1,354 total
includes taxes & fees
Apr 21 - Apr 22
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

Spacious home near the beach with deck, W/D, AC, & central location

2.0 star property
Spacious home near the beach with deck, W/D, AC, & central location

Charming coastal home with large yard, firepit, & grill - pool and beach access

9.6 out of 10, Exceptional, (16)
"Our family was so impressed with this house! Every single element was thought of- the location was perfect and it was such a lovely stay. We hope to be back!"
Charming coastal home with large yard, firepit, & grill - pool and beach access

Beachside Village Resort

3.0 star property
9.2 out of 10, Wonderful, (90)
"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

5BD 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"
5BD Tranquil Falmouth Breeze Escape w/ Pool

Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC

9.8 out of 10, Exceptional, (6)
"Perfect location. Great size for 2-4 people."
Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC

Adorable waterfront home w/ boat access & a three-season sunroom

8.4 out of 10, Very good, (29)
"Came to the Cape to fish the bay and other areas. Had a great time and loved the use of the dock, which worked fine for my shallow draft boat. "
Adorable waterfront home w/ boat access & a three-season sunroom

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

10.0 out of 10, Exceptional, (163)
"Perfect place "
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Newly Renovated Martha's Vineyard Vacation Rental!

9.8 out of 10, Exceptional, (41)
"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 CA $277
CA $856 total
includes taxes & fees
Apr 21 - Apr 22
Newly Renovated Martha's Vineyard Vacation Rental!

Breathtaking Views with Private Dock & Pool!

9.2 out of 10, Wonderful, (21)
"Great location. Loved the deck overlooking the water, the dock, the kayaks and the pool right next to the house. We mostly stayed around the house and the bay. Local free beach was close by with no one there on cooler windy days. Host, Maria, was very responsive to questions we had."
Breathtaking Views with Private Dock & Pool!

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

9.6 out of 10, Exceptional, (78)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is CA $415
CA $742 total
includes taxes & fees
Apr 21 - Apr 22
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

8.8 out of 10, Excellent, (9)
"Private with beach access minutes away."
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Sea Crest Beach Resort

3.5 star property
8.4 out of 10, Very good, (60)
"Love this hotel"
The price is CA $183
CA $289 total
includes taxes & fees
May 1 - May 2
Sea Crest Beach Resort

Iris Hotel Cape Cod

3.0 star property
7.0 out of 10, Good, (6)
"Found my room clean, the staff help and the facility very guest friendly!"
The price is CA $141
CA $162 total
includes taxes & fees
Apr 23 - Apr 24
Iris Hotel Cape Cod
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 vacation rentals in Chilmark?

Yes, there are vacation rentals in Chilmark near Chilmark Chocolates, or you can select a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals that Chilmark has to offer?

Summer home with expansive deck & wonderful location for beachgoers: This vacation home near Chilmark is located near the bay and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals are there in Chilmark?

Choose from 69 Expedia vacation rentals in Chilmark for a memorable vacation.

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 vacation rental in Chilmark like?

A vacation rental is a private property where you can stay for a long or short time in Chilmark. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for a family getaway.