Holiday Rentals in Chilmark

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Our top choices for Chilmark holiday rentals

Condo resort in New Seabury

The Club at New Seabury
3.5 star property
9.0 out of 10, Wonderful, (353 reviews)
"Everything was superb, accommodations, check in service, check out service!!"
United States
Dianna
The Club at New Seabury

Aparthotel in Falmouth Heights

InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (200 reviews)
"This is my go to hotel when I’m in Falmouth. Always clean and the staff are very friendly. The one bedroom units are very nice!"
United States
Jeff
InnSeason Resorts Captain's Quarters
8.2 out of 10, Very good, (24 reviews)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is €172
includes taxes & fees
6 Mar - 7 Mar
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
10.0 out of 10, Exceptional, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is €365
includes taxes & fees
3 Mar - 4 Mar
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
8.6 out of 10, Excellent, (91 reviews)
"Property needs a refresh."
United States
Paul B.
The price is €522
includes taxes & fees
12 Mar - 13 Mar
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
10.0 out of 10, Exceptional, (17 reviews)
"Great location, clean house. Well stocked with supplies and beach items."
United States
Tyler M.
The price is €325
includes taxes & fees
15 Mar - 16 Mar
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1

Holiday Home in Oak Bluffs

Oak Bluffs - Quiet neighborhood
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
The price is €574
includes taxes & fees
4 Mar - 5 Mar
Oak Bluffs - Quiet neighborhood
10.0 out of 10, Exceptional, (8 reviews)
"Great place"
United States
Aaron Q.
The price is €1,032
includes taxes & fees
29 Mar - 30 Mar
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful cottage ! Immaculately kept! Sunsets at night were amazing to watch. Very comfortable and inviting home. Definitely recommend a nice stay ! "
United States
ralpjh c.
The price is €366
includes taxes & fees
1 Mar - 2 Mar
Charming cottage overlooking the bay in Padanaram Village.
9.4 out of 10, Exceptional, (3 reviews)
"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 €750
includes taxes & fees
1 Mar - 2 Mar
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Holiday Home in Falmouth

Falmouth Oasis
The price is €416
includes taxes & fees
31 Mar - 1 Apr
Falmouth Oasis
10.0 out of 10, Exceptional, (7 reviews)
"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 €1,033
includes taxes & fees
1 Mar - 2 Mar
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
The price is €624
includes taxes & fees
16 Mar - 17 Mar
Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod

Holiday Home in Falmouth

Cape Cod Escape at Casa de Leo!
The price is €1,304
includes taxes & fees
1 Mar - 2 Mar
Cape Cod Escape at Casa de Leo!
10.0 out of 10, Exceptional, (16 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is €911
includes taxes & fees
29 Mar - 30 Mar
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
9.8 out of 10, Exceptional, (16 reviews)
"Overall great experience"
United States
Scott P.
The price is €912
includes taxes & fees
1 Mar - 2 Mar
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
9.4 out of 10, Exceptional, (91 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is €417
includes taxes & fees
1 Mar - 2 Mar
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
10.0 out of 10, Exceptional, (14 reviews)
"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 €1,205
includes taxes & fees
1 Mar - 2 Mar
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
9.4 out of 10, Exceptional, (88 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is €417
includes taxes & fees
1 Mar - 2 Mar
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
9.8 out of 10, Exceptional, (8 reviews)
"Great stay! Great property!"
United States
Liz A.
The price is €1,565
includes taxes & fees
9 Mar - 10 Mar
The Beach Estate, Panoramic Ocean Views, 5700 sqft
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 €365 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 chic meets French Provençal in this newly renovated oceanfront home. : This holiday home rental outside of Chilmark is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease 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 can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Chilmark?

Choose from 61 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.