Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
Apr 10 - Apr 12
In two months
May 22 - May 24
In three months
Jun 19 - Jun 21
In four months
Jul 17 - Jul 19

Our top choices for Chilmark vacation rentals

Property grounds

Cottage in New Seabury

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
$543 nightly
The price is $621
Mar 24 - Mar 25
Total with taxes and fees
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
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.
$322 nightly
The price is $360
Mar 24 - Mar 25
Total with taxes and fees
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1
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.
$387 nightly
The price is $432
Mar 24 - Mar 25
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
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.
$480 nightly
The price is $549
Mar 24 - Mar 25
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Exterior

Vacation Home in Falmouth

Falmouth Oasis
$434 nightly
The price is $497
Mar 24 - Mar 25
Total with taxes and fees
Falmouth Oasis
Interior

Apartment in Tisbury

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
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.
$446 nightly
The price is $498
Mar 24 - Mar 25
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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.
$1,085 nightly
The price is $1,212
Mar 24 - Mar 25
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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.
$600 nightly
The price is $670
Mar 28 - Mar 29
Total with taxes and fees
Oak Bluffs - Quiet neighborhood
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.
$800 nightly
The price is $894
Mar 24 - Mar 25
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
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.
$1,002 nightly
The price is $1,147
Mar 24 - Mar 25
Total with taxes and fees
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.
$946 nightly
The price is $1,056
Mar 24 - Mar 25
Total with taxes and fees
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
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.
$1,364 nightly
The price is $1,523
Mar 24 - Mar 25
Total with taxes and fees
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
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.
$446 nightly
The price is $498
Mar 24 - Mar 25
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Fridge, microwave, oven, stovetop

Vacation Home in Falmouth

Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod
$639 nightly
The price is $731
Apr 6 - Apr 7
Total with taxes and fees
Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod
Property grounds

Apartment in Falmouth

Beachside Village Resort
3.0 star property
9.4 out of 10, Exceptional, (101 reviews)
"Wonderful location, nice staff!"
United States
Claire
$999 nightly
The price is $1,143
Mar 24 - Mar 25
Total with taxes and fees
Beachside Village Resort
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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Top Chilmark Hotel Reviews

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

6/10 Okay
"Clean room. Good place to crash."
David 1-night trip
Posted 6 hours ago
Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Find out more about Chilmark

Everything you need to know about Chilmark vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chilmark vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chilmark vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chilmark. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chilmark in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $549 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chilmark rentals

At Expedia, we put the best Chilmark vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chilmark rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chilmark vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chilmark. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 62 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 Squibnocket Pond 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.