Chilmark Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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
$147 nightly
The price is $169
Nov 18 - Nov 19
Total with taxes and fees
The Club at New Seabury
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

2. 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.
$343 nightly
The price is $383
Nov 8 - Nov 9
Total with taxes and fees
Walk to Beach & Lighthouse: Oak Bluffs Studio!
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.

3. 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.
$397 nightly
The price is $443
Nov 11 - Nov 12
Total with taxes and fees
Vineyard Luxury "Yurt"
Room

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

Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
Oak Bluffs
$240 nightly
The price is $268
Nov 11 - Nov 12
Total with taxes and fees
Sunlit Studio Retreat with Incredible Outdoor Deck on Martha’s Vineyard
A view through a window with a wooden frame, overlooking a garden with various plants and a body of water in the background.

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.
$473 nightly
The price is $528
Nov 11 - Nov 12
Total with taxes and fees
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
A rocky beach with clear water, a sandy shore, and a hilly landscape in the background.

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.
$618 nightly
The price is $690
Nov 11 - Nov 12
Total with taxes and fees
Oak Bluffs 4BR • 5 Min Drive to Downtown
A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

7. 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.
$202 nightly
The price is $231
Nov 5 - Nov 6
Total with taxes and fees
Charming studio in tranquil Falmouth with AC
A boat docked at a concrete pier with a sandy shore in the background.

8. 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.
$379 nightly
The price is $433
Nov 5 - Nov 6
Total with taxes and fees
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A room with a view of the sea through large windows, a wooden deck, and a pier with structures.

9. 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, (98 reviews)
"Great location. Clear instructions"
United States
Sherise M.
$423 nightly
The price is $472
Nov 5 - Nov 6
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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.
$518 nightly
The price is $593
Nov 6 - Nov 7
Total with taxes and fees
Charming Guesthouse | Walk to Beach | Downtown
A room with a white dresser, a lamp, a window with blinds, and a view of a deck and houses outside.

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

Backyard Retreat / 5 Min > Beach & Main St
Fairhaven
$491 nightly
The price is $548
Nov 9 - Nov 10
Total with taxes and fees
Backyard Retreat / 5 Min > Beach & Main St
An outdoor seating area with Adirondack chairs and a table, surrounded by trees.

12. Walk to Beach! Oak Bluffs Home & Studio

Walk to Beach! Oak Bluffs Home & Studio
Oak Bluffs
$737 nightly
The price is $823
Nov 5 - Nov 6
Total with taxes and fees
Walk to Beach! Oak Bluffs Home & Studio
A spacious kitchen with a central island, stainless steel appliances, and a dining area with a rug and chairs.

13. 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, (227 reviews)
"Great location "
United States
Stephanie B.
$457 nightly
The price is $523
Nov 5 - Nov 6
Total with taxes and fees
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
A modern kitchen with white cabinetry, a dining area with a wooden table and white chairs, and a large window providing natural light.

14. 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.
$1,492 nightly
The price is $1,667
Nov 15 - Nov 16
Total with taxes and fees
New 4 BR house near center and beaches with bikes
A modern kitchen with white cabinetry, a black stove, and a stainless steel sink.

15. West Falmouth Family Retreat Near Chapoquoit Beach

West Falmouth Family Retreat Near Chapoquoit Beach
Falmouth
$956 nightly
The price is $1,094
Nov 5 - Nov 6
Total with taxes and fees
West Falmouth Family Retreat Near Chapoquoit Beach
A water park with a large central pool, multiple slides, and a variety of play structures.

16. 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)
"Beautiful and relaxing location."
United States
Lauren F.
$429 nightly
The price is $479
Nov 30 - Dec 1
Total with taxes and fees
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!
Interior

17. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (17 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
$479 nightly
The price is $535
Nov 26 - Nov 27
Total with taxes and fees
Charming cottage overlooking the bay in Padanaram Village.
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.
$609 nightly
The price is $697
Nov 29 - Nov 30
Total with taxes and fees
Stunning 4-bedroom Private Fresh Water Beach Front
A two-story house with a stone facade, a covered patio, and a well-maintained garden.

19. 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.
$2,713 nightly
The price is $3,030
Nov 30 - Dec 1
Total with taxes and fees
Beautiful Estate with salt water pool & pond with kayaks
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.
$719 nightly
The price is $823
Dec 1 - Dec 2
Total with taxes and fees
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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Find vacation rentals that suit your style

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Top Chilmark Hotel Reviews

A modern kitchen with white cabinets, a stainless steel island, and bar stools.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach
Vineyard Haven

10/10 Excellent

Location, cleanliness, beachfront!
United States
Martina
Reviewed October 14, 2024
Vineyard Harbor Motel - Private Beach

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 $168 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?

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.

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