Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
Jan 30 - Feb 1
In two months
Mar 13 - Mar 15
In three months
Apr 10 - Apr 12
In four months
May 8 - May 10

Our top choices for Chilmark vacation rentals

Private beach nearby, beach bar

Condo resort in New Seabury

The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (345 reviews)
"The place was excellent"
United States
Delia
$144 nightly
The price is $165
Jan 19 - Jan 20
Total with taxes and fees
The Club at New Seabury
On the beach, white sand

Aparthotel in Falmouth Heights

InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (197 reviews)
"This is my go to hotel when I’m in Falmouth. Always clean and the staff are very friendly. The one bedroom units are very nice!"
United States
Jeff
$117 nightly
The price is $134
Jan 19 - Jan 20
Total with taxes and fees
InnSeason Resorts Captain's Quarters
Beach nearby

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.
$175 nightly
The price is $200
Jan 19 - Jan 20
Total with taxes and fees
Near Old Silver Beach Falmouth- Two bedroom , private bathroom and kitchenette.
Interior

Cottage in Dartmouth

Charming cottage overlooking the bay in Padanaram Village.
2.0 star property
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.
$390 nightly
The price is $435
Feb 1 - Feb 2
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
Exterior

Vacation Home in Falmouth

Falmouth Oasis
2.0 star property
$380 nightly
The price is $435
Jan 19 - Jan 20
Total with taxes and fees
Falmouth Oasis
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)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
$432 nightly
The price is $494
Jan 19 - Jan 20
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Smart TV, DVD player

Vacation Home in Katama

The Seashell Cove - Martha's Vineyard
9.8 out of 10, Exceptional, (24 reviews)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
$514 nightly
The price is $574
Jan 26 - Jan 27
Total with taxes and fees
The Seashell Cove - Martha's Vineyard
Terrace/patio

Vacation Home in Oak Bluffs

Oak Bluffs - Quiet neighborhood
9.4 out of 10, Exceptional, (43 reviews)
"perfect for our needs"
United States
Ed V.
$566 nightly
The price is $632
Jan 21 - Jan 22
Total with taxes and fees
Oak Bluffs - Quiet neighborhood
Terrace/patio

Vacation Home in Falmouth

Spring Escape in Hatchville – Sleeps 6 + Dogs!
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
$620 nightly
The price is $710
Jan 19 - Jan 20
Total with taxes and fees
Spring Escape in Hatchville – Sleeps 6 + Dogs!
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
Jan 19 - Jan 20
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.
$996 nightly
The price is $1,140
Jan 19 - Jan 20
Total with taxes and fees
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Interior

Vacation Home in Falmouth

Cape Cod Escape at Casa de Leo!
2.5 star property
$1,266 nightly
The price is $1,448
Jan 19 - Jan 20
Total with taxes and fees
Cape Cod Escape at Casa de Leo!
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.
$1,220 nightly
The price is $1,363
Jan 19 - Jan 20
Total with taxes and fees
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
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
Jan 19 - Jan 20
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Terrace/patio

Vacation Home in Edgartown

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
9.8 out of 10, Exceptional, (16 reviews)
"The hosts are excellent people, great communicators who want VBRO guests to have an outstanding experience. Chappy is a wonderful retreat from the rest of the world. That is my only word of caution, it requires a ferry to eat out or shop. Otherwise this is a great place to read write meditate beach and let go of everyday worries. It has a higher price tag because your paying for a premium location, guest service experience and higher quality accomodation."
United States
SparkleCappy
$950 nightly
The price is $1,061
Jan 31 - Feb 1
Total with taxes and fees
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
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.
$971 nightly
The price is $1,085
Jan 20 - Jan 21
Total with taxes and fees
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Exterior

Vacation Home in Mattapoisett

The Beach Estate, Panoramic Ocean Views, 5700 sqft
9.8 out of 10, Exceptional, (8 reviews)
"Great stay! Great property!"
United States
Liz A.
$1,573 nightly
The price is $1,663
Feb 11 - Feb 12
Total with taxes and fees
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Smart TV

Apartment in Oak Bluffs

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
9.4 out of 10, Exceptional, (88 reviews)
"Very happy. Thank you for the stay."
United States
Gillian S.
$599 nightly
The price is $669
Jan 19 - Jan 20
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
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.
$574 nightly
The price is $641
Jan 19 - Jan 20
Total with taxes and fees
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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Top Chilmark Hotel Reviews

Falmouth Tides

Falmouth Tides

10/10 Excellent
"The beachiest stay! Soothed by the sound of the ocean at night and wake up to the best views. "
Emily 2-night trip
Posted 17 hours ago
Falmouth Tides

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 $134 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?

9-bedroom vacation home near Cape Cod Beaches: This vacation home rental near Chilmark is located in the city center and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Chilmark?

Choose from 75 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.