A dock with boats, a small wooden structure, and a forested shoreline.

Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chilmark vacation rentals

A two-story house with a swimming pool, a covered patio, and a fenced backyard.

1. Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (26 reviews)
"This is a great property for an individual or a couple looking to explore the island!"
United States
Jillian G.
$537 nightly
The price is $600
Oct 13 - Oct 14
Total with taxes and fees
Cozy efficiency apartment/heated pool
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

2. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
$147 nightly
The price is $169
Nov 1 - Nov 2
Total with taxes and fees
The Club at New Seabury
A modern kitchen with a marble countertop, a central island, and a hanging light fixture.

3. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (32 reviews)
"This property is quiet yet close enough to the business areas. Very clean, well maintained lovely unit with balcony. The host Joziane commutated with us from minutes after the booking to the end of stay, very helpful."
United States
Unspecified U.
$409 nightly
The price is $456
Oct 12 - Oct 13
Total with taxes and fees
Brand new! Lovely apartment-Vineyard Haven
A spacious living area with a high ceiling, a dining table, and a kitchen area.

4. A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.6 out of 10, Exceptional, (10 reviews)
"The host was very responsive.We definitely recommend this house as family friendly."
United States
Karen M.
$965 nightly
The price is $1,078
Oct 12 - Oct 13
Total with taxes and fees
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

5. Oak Bluffs 4BR • 5 Min Drive to Downtown

Oak Bluffs 4BR • 5 Min Drive to Downtown
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"This place was just what we needed! Would definitely stay again. Cozy and feels very homey! Thanks!"
United States
Chris S.
$685 nightly
The price is $765
Nov 11 - Nov 12
Total with taxes and fees
Oak Bluffs 4BR • 5 Min Drive to Downtown
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

6. Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (11 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.
$445 nightly
The price is $497
Oct 18 - Oct 19
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A living room with a flat-screen TV on a stand, a black leather chair, and a sofa. There are two windows with curtains, one of which offers a view of the sea.

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

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (97 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
$446 nightly
The price is $498
Oct 13 - Oct 14
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A residential area with a well-maintained lawn, a stone retaining wall, and a two-story house with a blue door.

8. New 4 BR house near center and beaches with bikes

New 4 BR house near center and beaches with bikes
Katama
9.8 out of 10, Exceptional, (12 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
$1,492 nightly
The price is $1,667
Oct 12 - Oct 13
Total with taxes and fees
New 4 BR house near center and beaches with bikes
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

9. Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
Oak Bluffs
9.8 out of 10, Exceptional, (10 reviews)
"The property was clean, private, and peaceful."
United States
Sherri R.
$1,222 nightly
The price is $1,365
Oct 12 - Oct 13
Total with taxes and fees
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

10. MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (12 reviews)
"This was an excellent stay at a beautiful property in Oak Bluffs! Rebecca was a great host who provided clear instructions and helped answer questions in a timely manner. Rooms were spacious, most tastefully decorated and we had everything that we needed. I definitely recommend staying here to have an unparalleled experience of the Vineyard."
United States
Priyanka D.
$1,917 nightly
The price is $2,141
Oct 12 - Oct 13
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A modern living room with a sofa, chairs, a coffee table, and a dining area.

11. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (92 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
$280 nightly
The price is $321
Oct 14 - Oct 15
Total with taxes and fees
New Seabury Cape Condo + Pool & Beach Escape
A backyard with a seating area, a white fence, and a variety of plants.

12. Delightful 3-bedroom house with AC in Oak Bluffs

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
$1,025 nightly
The price is $1,145
Oct 30 - Oct 31
Total with taxes and fees
Delightful 3-bedroom house with AC in Oak Bluffs
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

13. Walk to Beach & Lighthouse: Oak Bluffs Studio!

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (13 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
$557 nightly
The price is $622
Oct 12 - Oct 13
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

14. 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, (224 reviews)
"Great location "
United States
Stephanie B.
$455 nightly
The price is $521
Nov 1 - Nov 2
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A circular stone patio with Adirondack chairs and a small table in a forested area.

15. 1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
Oak Bluffs
7.0 out of 10, Good, (12 reviews)
"Loved this spot. Perfect central island location. Fantastic owner with an incredible response time. Would recommend this property to all5 stars"
United States
Eli R.
$635 nightly
The price is $709
Oct 12 - Oct 13
Total with taxes and fees
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

16. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfy place, a short drive to Falmouth center! Communication was very easy and check-in simple."
United States
Harry H.
$213 nightly
The price is $244
Oct 12 - Oct 13
Total with taxes and fees
Charming studio in tranquil Falmouth with AC
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

17. Beautiful Estate with salt water pool & pond with kayaks

Beautiful Estate with salt water pool & pond with kayaks
Oak Bluffs
10.0 out of 10, Exceptional, (3 reviews)
"Brenda and Derek were amazing hosts. They have a beautifully landscaped property with all the amenities needed for a relaxing family vacation. They are super responsive and take a lot of pride in giving their guests a top-notch experience. We will definitely consider staying at their properties again."
United States
Lamar A.
$3,399 nightly
The price is $3,797
Oct 12 - Oct 13
Total with taxes and fees
Beautiful Estate with salt water pool & pond with kayaks
A spacious living area with wooden beams, a dining table, and a sofa.

18. The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (31 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
$1,051 nightly
The price is $1,174
Oct 14 - Oct 15
Total with taxes and fees
The Seashell Cove - Martha's Vineyard
A deck with a fire pit, outdoor seating, and a blue umbrella.

19. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (9 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
$742 nightly
The price is $849
Oct 12 - Oct 13
Total with taxes and fees
Cozy Cottage walk to Menauhant Beach
A boat docked at a concrete pier with a sandy shore in the background.

20. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (44 reviews)
"Great stay!"
United States
Kian S.
$398 nightly
The price is $456
Oct 18 - Oct 19
Total with taxes and fees
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
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

Summercamp

Summercamp

10/10 Excellent
"Magical stay! This place was perfection for location… vibe…. Feel and moments."
Andre 1-night trip
Posted 11 hours ago
Summercamp

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 $169 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.

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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 Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: This vacation home near Chilmark is located near the beach 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.

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.