Photo by Wen C.

Chilmark Holiday Rentals

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Holiday Rentals in Chilmark

The Club at New Seabury

3.5 star property
Mashpee
9.0 out of 10, Wonderful, (336)
"Great stay! Didn't notice it being dated or dirty at all like some reviews said. We loved it!"
United States
Rachael
The Club at New Seabury

Charming cottage overlooking the bay in Padanaram Village.

2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (10)
"Beautiful property. The cottage is beautifully decorated and well maintained. Amazing location. Host was very good at communicating. "
United States
christine l.
The price is NZ$664
includes taxes & fees
13 Nov - 14 Nov
Charming cottage overlooking the bay in Padanaram Village.

Sea Mist Resort

3.0 star property
Mashpee
8.6 out of 10, Excellent, (140)
"We had a fabulous visit!"
United States
Joelle
Sea Mist Resort

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Falmouth
10.0 out of 10, Exceptional, (206)
"The house was even nicer than the pictures. We came in March for a long weekend with some friends and had a really great time. Walking distance to so many fun things- great house for all ages!"
United States
Briget R.
The price is NZ$878
includes taxes & fees
13 Nov - 14 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Westport
9.8 out of 10, Exceptional, (22)
"We enjoyed our stay and recommend It. Delightful back yard and patio area and a very pleasant front porch."
United States
Alan M.
The price is NZ$747
includes taxes & fees
13 Nov - 14 Nov
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village

Newly Renovated Martha's Vineyard Vacation Rental!

Katama
9.6 out of 10, Exceptional, (47)
"Very nice house that served our needs. Well located. Nicely appointed. The bedroom downstairs with twin beds accommodated my elderly mother who has trouble with stairs. No real maintenance issues other than, the gfci outlets in the bathrooms did not work."
United States
Silvia B.
The price is NZ$1,045
includes taxes & fees
25 Nov - 26 Nov
Newly Renovated Martha's Vineyard Vacation Rental!

Charming studio in tranquil Falmouth with AC

Falmouth
The price is NZ$367
includes taxes & fees
13 Nov - 14 Nov
Charming studio in tranquil Falmouth with AC

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Falmouth
10.0 out of 10, Exceptional, (11)
"We LOVED our stay. The home is gorgeous and comfortable with everything we needed. The kids loved the game barn. Nicely located. We loved the deck. Would stay again!"
United States
Enid G.
The price is NZ$1,278
includes taxes & fees
13 Nov - 14 Nov
Spring Escape in Hatchville – Sleeps 6 + Dogs!

The Seashell Cove - Martha's Vineyard

Katama
9.8 out of 10, Exceptional, (23)
"My family and I had a great stay in this lovely home!! The house had everything we needed and was a great starting point for all island adventures. Charles was so helpful throughout the entire trip. We would most certainly stay here again!"
United States
Caryn I.
The price is NZ$1,015
includes taxes & fees
8 Dec - 9 Dec
The Seashell Cove - Martha's Vineyard

NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

Tisbury
10.0 out of 10, Exceptional, (16)
"The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future."
United States
Betel G.
The price is NZ$1,918
includes taxes & fees
1 Dec - 2 Dec
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

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

East Falmouth
10.0 out of 10, Exceptional, (88)
"This is a lovely property for a family beach vacation! The property has a wonderful view of the ocean, easy access to a beach, and is close to many great restaurants and things to do. Our host was very responsive and accommodating throughout our stay. I would highly recommend. "
United States
Andrew H.
The price is NZ$1,797
includes taxes & fees
8 Dec - 9 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs
9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
United States
Leon R.
The price is NZ$1,580
includes taxes & fees
21 Nov - 22 Nov
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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

Mashpee
10.0 out of 10, Exceptional, (8)
"We had a great time in this rental. The house is a perfect set up for families and/or friends with bedrooms on lower level, and two en-suite masters. The location is perfect. Walking distance to a beach and beautiful neighborhood. Views of the water on the second floor balconies. Would rent again!"
United States
Michelle A.
The price is NZ$2,018
includes taxes & fees
25 Nov - 26 Nov
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Oak Bluffs
10.0 out of 10, Exceptional, (7)
"This home is truly that, a welcoming escape nestled in the woods. It’s elevated beach-style furnishings feel hand-picked. We traveled with a 14 month old — the house had high-quality baby must haves, pack and play and high chair. We had the pleasure of a responsive host and caretaker. Close to trails, YMCA and the island’s top attractions … !highly recommend!"
United States
Kerry-Ann H.
The price is NZ$2,143
includes taxes & fees
21 Nov - 22 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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

Dartmouth
10.0 out of 10, Exceptional, (13)
"Extremely well designed extremely comfortable and well appointed. Beautiful scenery, and very relaxing."
United States
David J.
The price is NZ$2,417
includes taxes & fees
26 Nov - 27 Nov
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views

Stones Throw Waterfront

Dartmouth
8.8 out of 10, Excellent, (6)
"According to the listing, the property has AC. That is not true. It had a tiny portable unit that wasn't on when we entered and didn't cool once it was turned on. It also had a window unit that had no place to plug in. There were bugs in multiple areas. The property was not habitable, so we ended up booking a hotel room in a nearby town. VRBO compensated us partially but the owner was unwilling to refund any of our money even though we did not stay in the property. "
United States
Ashley R.
The price is NZ$1,127
includes taxes & fees
24 Nov - 25 Nov
Stones Throw Waterfront

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

Oak Bluffs
9.4 out of 10, Exceptional, (88)
"Great location! No towels for shower "
United States
Jack B.
The price is NZ$881
includes taxes & fees
14 Nov - 15 Nov
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Cape cod getaway Close to Old Silver

Falmouth
The price is NZ$927
includes taxes & fees
17 Nov - 18 Nov
Cape cod getaway Close to Old Silver

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

Oak Bluffs
9.4 out of 10, Exceptional, (91)
"Location, the water view, delicious restaurants nearby. Apt was comfy, clean. For 1 night only used the fridge. "
United States
Brenda M.
The price is NZ$881
includes taxes & fees
15 Nov - 16 Nov
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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$881 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?

Newly Renovated Near Amazing Sunset Beach: This holiday home rental outside of Chilmark offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Chilmark?

Choose from 77 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 Lucy Vincent Beach 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.