Chilmark Vacation Rentals

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Our top choices for Chilmark vacation rentals

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.4 out of 10, Very Good, (25 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
$204 nightly
The price is $233
May 8 - May 9
Total with taxes and fees
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
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
May 8 - May 9
Total with taxes and fees
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (355 reviews)
"Our stay was great and Amy at the front desk is a god send she was absolutely the best."
United States
Jasmine
$232 nightly
The price is $265
Jun 3 - Jun 4
Total with taxes and fees
The Club at New Seabury

Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6
Popponesset
10.0 out of 10, Exceptional, (188 reviews)
"great stay! fantastic location."
United States
Emily P.
$729 nightly
The price is $834
May 17 - May 18
Total with taxes and fees
Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
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.
$397 nightly
The price is $443
May 13 - May 14
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (81 reviews)
"Host was super organized with clear instructions and easy check-in. The condo was well appointed and beautifully decorated. We enjoyed our brief stay!"
United States
Gina P.
$289 nightly
The price is $331
May 17 - May 18
Total with taxes and fees
New Seabury Cape Condo + Pool & Beach Escape

Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (25 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
$391 nightly
The price is $436
May 11 - May 12
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
$173 nightly
The price is $197
May 10 - May 11
Total with taxes and fees
Charming studio in tranquil Falmouth with AC

Falmouth Oasis

Falmouth Oasis
Falmouth
$429 nightly
The price is $491
May 10 - May 11
Total with taxes and fees
Falmouth Oasis

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
$742 nightly
The price is $829
May 26 - May 27
Total with taxes and fees
Charming Vacation Home in Oak Bluffs.

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
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
May 8 - May 9
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Edgartown Designer Cottage between Town & Beach.

Edgartown Designer Cottage between Town & Beach.
Katama
10.0 out of 10, Exceptional, (25 reviews)
"Wonderful week in MV! The cottage had everything we needed and was a great location to bike into town or to the beach. Would love to come back and stay again!"
United States
Lauren B.
$589 nightly
The price is $658
May 8 - May 9
Total with taxes and fees
Edgartown Designer Cottage between Town & Beach.

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (26 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
$743 nightly
The price is $830
May 10 - May 11
Total with taxes and fees
The Seashell Cove - Martha's Vineyard

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
$828 nightly
The price is $925
May 9 - May 10
Total with taxes and fees
4-bedroom house in lovely Edgartown..Centrally located

LUX on Main | Downtown | Parking | Sleeps 6, #201

LUX on Main | Downtown | Parking | Sleeps 6, #201
Falmouth
$565 nightly
The price is $652
May 9 - May 10
Total with taxes and fees
LUX on Main | Downtown | Parking | Sleeps 6, #201

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (216 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
$480 nightly
The price is $549
May 10 - May 11
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
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
May 8 - May 9
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Tisbury
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.
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
$646 nightly
The price is $739
May 8 - May 9
Total with taxes and fees
Spring Escape in Hatchville – Sleeps 6 + Dogs!

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
Westport
9.8 out of 10, Exceptional, (24 reviews)
"We loved our stay! The house was so comfortable and welcoming. Great location and wonderful space would definitely stay there again! "
United States
Kim D.
$520 nightly
The price is $581
May 11 - May 12
Total with taxes and fees
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
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

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 $233 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.

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?

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool. : This vacation home rental near Chilmark is located near the beach and has a patio, a private yard, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 65 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.