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

Holiday Rentals in Chilmark

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Our top choices for Chilmark holiday rentals

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 €177
includes taxes & fees
1 Nov - 2 Nov
The Club at New Seabury

2. 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.
The price is €434
includes taxes & fees
21 Oct - 22 Oct
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

3. Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
10.0 out of 10, Exceptional, (33 reviews)
"Fabulous property! Clean and very comfy."
United States
Claudia
The price is €470
includes taxes & fees
18 Oct - 19 Oct
Brand new! Lovely apartment-Vineyard Haven

4. 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.
The price is €298
includes taxes & fees
22 Oct - 23 Oct
New Seabury Cape Condo + Pool & Beach Escape

5. 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)
"A clean accommodating space with an accommodating host - I recommended!"
United States
Collins E.
The price is €970
includes taxes & fees
15 Oct - 16 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

6. 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 €672
includes taxes & fees
11 Nov - 12 Nov
Oak Bluffs 4BR • 5 Min Drive to Downtown

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

Delightful 3-bedroom house with AC in Oak Bluffs
Oak Bluffs
The price is €1,038
includes taxes & fees
30 Oct - 31 Oct
Delightful 3-bedroom house with AC in Oak Bluffs

8. 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.
The price is €546
includes taxes & fees
19 Oct - 20 Oct
Walk to Beach & Lighthouse: Oak Bluffs Studio!

9. Backyard Retreat / 5 Min > Beach & Main St

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
The price is €600
includes taxes & fees
19 Oct - 20 Oct
Backyard Retreat / 5 Min > Beach & Main St

10. 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 stay!"
United States
Kian S.
The price is €412
includes taxes & fees
8 Nov - 9 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

11. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
West Falmouth Family Retreat Near Chapoquoit Beach

12. 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 €1,222
includes taxes & fees
15 Oct - 16 Oct
Relax by Oak Bluffs Harbor, enjoy your 3-bedroom East Chip retreat

13. 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.
Charming studio in tranquil Falmouth with AC

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 €650
includes taxes & fees
19 Oct - 20 Oct
1 Mi to Ferry Terminal: Oak Bluffs Family Retreat!

15. 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.
The price is €467
includes taxes & fees
1 Nov - 2 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

16. 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
The price is €448
includes taxes & fees
15 Oct - 16 Oct
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

17. LUX on Main | Downtown | Parking | Sleeps 6, #203

LUX on Main | Downtown | Parking | Sleeps 6, #203
Falmouth
10.0 out of 10, Exceptional, (6 reviews)
The price is €679
includes taxes & fees
15 Oct - 16 Oct
LUX on Main | Downtown | Parking | Sleeps 6, #203

18. 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 €1,480
includes taxes & fees
15 Oct - 16 Oct
New 4 BR house near center and beaches with bikes

19. 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 €1,974
includes taxes & fees
15 Oct - 16 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

20. 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 €565
includes taxes & fees
15 Oct - 16 Oct
Charming Guesthouse | Walk to Beach | Downtown
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chilmark holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chilmark holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chilmark holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chilmark holiday rentals we have selected for you start as low as €177 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chilmark rentals

At Expedia, we put the best Chilmark holiday 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 holiday.

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 holiday rentals in Chilmark?

Yes, there are holiday rentals in Chilmark close to Chilmark Chocolates, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chilmark has to offer?

Coastal Retreat | Walk to Inkwell Beach, Dining & Flying Horses Carousel: This holiday home rental outside of Chilmark is located near the beach, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Chilmark?

Choose from 65 Expedia holiday rentals in Chilmark for a memorable holiday.

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 holiday rental in Chilmark like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chilmark. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a small group gathering.