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Chilmark Holiday Rentals

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Our top choices for Chilmark holiday rentals

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
Cozy efficiency apartment/heated pool

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (341)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The Club at New Seabury

InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (193)
"Best scenery ever !"
United States
Jacqueline
The price is NZ$255
includes taxes & fees
4 Jan - 5 Jan 2026
InnSeason Resorts Captain's Quarters

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (11)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is NZ$675
includes taxes & fees
2 Jan - 3 Jan 2026
Charming cottage overlooking the bay in Padanaram Village.

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (8)
"This property was beautiful! The hosts were excellent and were always available to message. I would recommend a stay at this home."
United States
Lisa Mason D.
The price is NZ$926
includes taxes & fees
16 Jan - 17 Jan 2026
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath
Falmouth
8.2 out of 10, Very good, (24)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is NZ$345
includes taxes & fees
1 Jan - 2 Jan 2026
Near Old Silver Beach Falmouth-Private entrance, private bedroom & shared bath

Falmouth Oasis

Falmouth Oasis
2.0 star property
Falmouth
The price is NZ$749
includes taxes & fees
4 Jan - 5 Jan 2026
Falmouth Oasis

Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (88)
"This is an excellent home well-kept great location, and the Host is easy to communicate with. "
United States
Gary B.
The price is NZ$2,091
includes taxes & fees
3 Jan - 4 Jan 2026
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Newly Renovated Martha's Vineyard Vacation Rental!

Newly Renovated Martha's Vineyard Vacation Rental!
Katama
9.6 out of 10, Exceptional, (47)
"We really enjoyed our stay. The house was conveniently located near Edgartown and South Beach in a quiet neighborhood. The house had everything we needed and more and was in great shape. Would definitely stay here again. "
United States
Patrick S.
The price is NZ$1,263
includes taxes & fees
1 Jan - 2 Jan 2026
Newly Renovated Martha's Vineyard Vacation Rental!

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, (211)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
The price is NZ$851
includes taxes & fees
4 Jan - 5 Jan 2026
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is NZ$989
includes taxes & fees
5 Jan - 6 Jan 2026
The Seashell Cove - Martha's Vineyard

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
New Seabury
10.0 out of 10, Exceptional, (79)
"We were extremely happy with our stay. The condo was beautiful, had everything we needed. Looking forward to coming back again next year for a longer stay"
United States
Beth H.
The price is NZ$685
includes taxes & fees
2 Jan - 3 Jan 2026
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

Edgartown Designer Retreat

Edgartown Designer Retreat
2.0 star property
Katama
The price is NZ$3,883
includes taxes & fees
1 Jan - 2 Jan 2026
Edgartown Designer Retreat

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)
"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.
The price is NZ$1,539
includes taxes & fees
1 Jan - 2 Jan 2026
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)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
The price is NZ$1,868
includes taxes & fees
1 Jan - 2 Jan 2026
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

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, (91)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is NZ$1,101
includes taxes & fees
1 Jan - 2 Jan 2026
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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)
"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.
The price is NZ$2,087
includes taxes & fees
1 Jan - 2 Jan 2026
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

The Beach Estate, Panoramic Ocean Views, 5700 sqft

The Beach Estate, Panoramic Ocean Views, 5700 sqft
Mattapoisett
9.8 out of 10, Exceptional, (8)
"This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!"
United States
Catherine T.
The price is NZ$3,111
includes taxes & fees
14 Jan - 15 Jan 2026
The Beach Estate, Panoramic Ocean Views, 5700 sqft

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
New Seabury
10.0 out of 10, Exceptional, (8)
"Nice house! Great area. Close to nice beach !"
United States
Cally G.
The price is NZ$1,967
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Dartmouth
10.0 out of 10, Exceptional, (14)
"Beautiful home, well maintained, incredibly hospitable and responsive host. Kitchen is well equipped and amply stocked with cooking essential and extras for feeding your guests. Wonderful spacious yard great for outdoor fun."
United States
Nick R.
The price is NZ$2,487
includes taxes & fees
4 Jan - 5 Jan 2026
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
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, 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 NZ$255 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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Chilmark is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chilmark?

Choose from 76 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.