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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chilmark vacation rentals

A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

1. 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
The price is ￥27,328
￥31,276 total
includes taxes & fees
Nov 11 - Nov 12
The Club at New Seabury
A spacious living area with a high ceiling, a dining table, and a kitchen area.

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

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.8 out of 10, Exceptional, (11 reviews)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is ￥78,042
￥169,944 total
includes taxes & fees
Oct 31 - Nov 1
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
A modern kitchen with stainless steel appliances, a dining area with a wooden table set for six, and a living area with a sofa and TV.

3. 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.
The price is ￥42,426
￥111,317 total
includes taxes & fees
Nov 11 - Nov 12
Oak Bluffs 4BR • 5 Min Drive to Downtown
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.

4. 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, (99 reviews)
"Memorial Day weekend on the Vineyard was perfect."
United States
Cassandra
The price is ￥42,568
￥78,543 total
includes taxes & fees
Nov 1 - Nov 2
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
A wooden deck with wicker chairs and a round table with a sun design.

5. 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)
"Cute, Cozy, comfortable, clean and quiet small apartment with full kitchen, a comfortable king bed with views of the lake from the kitchen/living room area and bedroom. It also had a nice spot outside on a deck with two chairs and table where we read, and watched the boats go by! Our host Stephen was very nice and helpful he responded quickly to our texts! The apt is near the bus route which is fabulous on the vineyard it goes to all the major spots you’d want to go! And it’s free!! It is also...
United States
Liz C.
The price is ￥47,298
￥84,531 total
includes taxes & fees
Nov 8 - Nov 9
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A modern kitchen with a large island, a dining area with a table and chairs, and a view of a green garden through large windows.

6. Vineyard Luxury "Yurt"

Vineyard Luxury "Yurt"
Oak Bluffs
10.0 out of 10, Exceptional, (1 review)
"The yurt was clean and nice and served all of our needs."
United States
David C.
The price is ￥45,091
￥83,475 total
includes taxes & fees
Nov 11 - Nov 12
Vineyard Luxury "Yurt"
A single-story house with a covered porch, a hammock, and a brick pathway leading to the front door.

7. 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.
The price is ￥62,749
￥215,555 total
includes taxes & fees
Oct 31 - Nov 1
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

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

Walk to Beach & Lighthouse: Oak Bluffs Studio!
Oak Bluffs
7.6 out of 10, Good, (14 reviews)
"The unit was clean and sufficient for 2 people. Outside could use some attention."
United States
Donna R.
The price is ￥24,280
￥63,575 total
includes taxes & fees
Nov 1 - Nov 2
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.

9. 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, (225 reviews)
"Great location "
United States
Stephanie B.
The price is ￥28,379
￥82,463 total
includes taxes & fees
Nov 1 - Nov 2
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Exterior

10. Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
10.0 out of 10, Exceptional, (1 review)
"The house was very convenient to the beach, Aldi’s, Walmart, and local restaurants & shops. I wasn’t sure how private it was being a guest house, but I never felt that we didn’t have privacy. Our dogs enjoyed the little fenced in yard. We appreciated the updated bathroom and kitchen. The weather was so pleasant a small outdoor area would have been nice, and we missed not having a washer & dryer and dishwasher, but overall it was clean and cozy. We would stay there again! We loved the Cape,...
United States
Kandy W.
The price is ￥28,518
￥97,958 total
includes taxes & fees
Nov 1 - Nov 2
Charming Guesthouse | Walk to Beach | Downtown
A modern interior with a wooden staircase, a kitchen area, and a living space with a sofa and coffee table.

11. 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.
The price is ￥212,841
￥352,036 total
includes taxes & fees
Oct 31 - Nov 1
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

12. 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, (13 reviews)
"Wonderful home in a beautiful neighborhood. Loved our stay!"
United States
Susan M.
The price is ￥94,281
￥276,487 total
includes taxes & fees
Nov 15 - Nov 16
New 4 BR house near center and beaches with bikes
Room

13. Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard

Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
Oak Bluffs
The price is ￥17,185
￥41,033 total
includes taxes & fees
Oct 31 - Nov 1
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
A circular stone patio with Adirondack chairs and a small table in a forested area.

14. 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.
The price is ￥41,465
￥101,965 total
includes taxes & fees
Nov 1 - Nov 2
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!
A spacious living area with wooden beams, a dining table, and a sofa.

15. 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.
The price is ￥106,421
￥176,108 total
includes taxes & fees
Nov 1 - Nov 2
The Seashell Cove - Martha's Vineyard
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, (4 reviews)
"Very clean and comfy place, a short drive to Falmouth center! Communication was very easy and check-in simple."
United States
Harry H.
The price is ￥25,541
￥37,351 total
includes taxes & fees
Oct 31 - Nov 1
Charming studio in tranquil Falmouth with AC
A patio with wicker chairs and a small table, a grassy yard, a wooden fence, and a view of a body of water.

17. 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, (45 reviews)
"Great place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is ￥24,831
￥68,839 total
includes taxes & fees
Nov 1 - Nov 2
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A wooden deck overlooking a calm lake with trees and houses in the background.

18. Stunning 4-bedroom Private Fresh Water Beach Front

Stunning 4-bedroom Private Fresh Water Beach Front
East Falmouth
10.0 out of 10, Exceptional, (45 reviews)
"Great trip and time on the lake. Highly recommend this property for families looking for ease and convenience."
United States
Kathryn C.
The price is ￥43,278
￥107,633 total
includes taxes & fees
Nov 1 - Nov 2
Stunning 4-bedroom Private Fresh Water Beach Front
A patio with outdoor furniture, a tree, and a lattice fence.

19. Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Fairhaven
9.6 out of 10, Exceptional, (40 reviews)
"The most perfect spot! Our host and the neighbors were so nice and gave us great tips! Would definitely stay again"
United States
Jainessa
The price is ￥35,474
￥79,601 total
includes taxes & fees
Nov 30 - Dec 1
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

20. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (19 reviews)
"Jessica was absolutely amazing and so was the house! We stayed here for our family vacation and it was perfect. 5 stars all around!"
United States
Kelsey B.
The price is ￥59,780
￥145,648 total
includes taxes & fees
Nov 1 - Nov 2
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
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

Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven

8/10 Good
"X"
Carlos 1-night trip
Posted 16 hours ago
Hampton Inn by Hilton New Bedford/Fairhaven

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:

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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.