Chilmark Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Chilmark vacation rentals

Interior

Cottage in Dartmouth

Charming cottage overlooking the bay in Padanaram Village.
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful cottage ! Immaculately kept! Sunsets at night were amazing to watch. Very comfortable and inviting home. Definitely recommend a nice stay ! "
United States
ralpjh c.
The price is ￥38,622
￥67,370 total
includes taxes & fees
Mar 10 - Mar 11
Charming cottage overlooking the bay in Padanaram Village.
Property grounds

Cottage in New Seabury

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
8.6 out of 10, Excellent, (91 reviews)
"Property needs a refresh."
United States
Paul B.
The price is ￥46,815
￥96,980 total
includes taxes & fees
Mar 3 - Mar 4
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Interior

Apartment in Falmouth

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
8.2 out of 10, Very Good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is ￥27,933
￥47,508 total
includes taxes & fees
Mar 6 - Mar 7
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Interior

Vacation Home in Falmouth

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is ￥18,414
￥68,406 total
includes taxes & fees
Mar 3 - Mar 4
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Exterior

Vacation Home in Falmouth

Falmouth Oasis
The price is ￥28,089
￥76,976 total
includes taxes & fees
Mar 3 - Mar 4
Falmouth Oasis
Outdoor dining

Vacation Home in Dartmouth

Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1
10.0 out of 10, Exceptional, (17 reviews)
"Great location, clean house. Well stocked with supplies and beach items."
United States
Tyler M.
The price is ￥21,067
￥54,908 total
includes taxes & fees
Mar 15 - Mar 16
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1
Exterior

Vacation Home in Tisbury

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is ￥78,025
￥169,253 total
includes taxes & fees
Mar 7 - Mar 8
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Interior

Vacation Home in Oak Bluffs

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
10.0 out of 10, Exceptional, (7 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is ￥85,828
￥189,125 total
includes taxes & fees
Mar 3 - Mar 4
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

Apartment in Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
9.4 out of 10, Exceptional, (91 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is ￥42,134
￥77,741 total
includes taxes & fees
Mar 3 - Mar 4
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Smart TV, DVD player

Vacation Home in Katama

The Seashell Cove - Martha's Vineyard
9.8 out of 10, Exceptional, (25 reviews)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is ￥39,013
￥89,595 total
includes taxes & fees
Mar 30 - Mar 31
The Seashell Cove - Martha's Vineyard
TV, fireplace, books

Vacation Home in Oak Bluffs

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
9.4 out of 10, Exceptional, (3 reviews)
"This house was perfect for our getaway. Rebecca, the host, was extremely responsive and helpful during our trip. The house was as advertised. It was clean, well equipped, and the location was perfect as well "
United States
Louis R.
The price is ￥54,618
￥139,447 total
includes taxes & fees
Mar 7 - Mar 8
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Smart TV, books

Vacation Home in Dartmouth

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."
United States
Nick R.
The price is ￥126,741
￥218,612 total
includes taxes & fees
Mar 3 - Mar 4
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Terrace/patio

Vacation Home in Oak Bluffs

Oak Bluffs - Quiet neighborhood
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
The price is ￥46,815
￥104,586 total
includes taxes & fees
Mar 11 - Mar 12
Oak Bluffs - Quiet neighborhood
Fridge, microwave, oven, stovetop

Vacation Home in Falmouth

Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod
The price is ￥58,519
￥114,483 total
includes taxes & fees
Mar 16 - Mar 17
Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod
Outdoor dining

Vacation Home in New Seabury

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
10.0 out of 10, Exceptional, (8 reviews)
"Great place"
United States
Aaron Q.
The price is ￥98,171
￥179,334 total
includes taxes & fees
Mar 12 - Mar 13
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Terrace/patio

Vacation Home in Edgartown

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
9.8 out of 10, Exceptional, (16 reviews)
"Overall great experience"
United States
Scott P.
The price is ￥110,249
￥165,680 total
includes taxes & fees
Mar 3 - Mar 4
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Interior

Apartment in Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
9.4 out of 10, Exceptional, (88 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is ￥46,815
￥83,668 total
includes taxes & fees
Mar 7 - Mar 8
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Interior

Vacation Home in Falmouth

Cape Cod Escape at Casa de Leo!
The price is ￥105,334
￥239,681 total
includes taxes & fees
Mar 3 - Mar 4
Cape Cod Escape at Casa de Leo!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chilmark Hotel Reviews

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Room spotless . Bed super comfortable. Staff nice and made me feel as if I were just back from a trip away!! What’s not to love!!"
John 1-night trip
Posted 3 days ago
Vineyard Harbor Motel - Private Beach

Find out more about Chilmark

Search for holiday rentals in Chilmark on Expedia! You can easily find your home rentals, villas, holiday apartments in Chilmark using one of the methods below:

  • View our selection of featured holiday rentals in Chilmark
  • Use the map to find apartments and other holiday homes in the Chilmark neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chilmark while they last

Look no further and take a look at our great range of rental properties in Chilmark!

Explore a world of travel with Expedia

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?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This vacation home rental near Chilmark is located on the beach and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Chilmark?

Choose from 61 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 Edys Island 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.