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

Chilmark Holiday Rentals

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Our top choices for Chilmark holiday rentals

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (362 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is NZ$1,017
includes taxes & fees
5 July - 6 July
The Club at New Seabury

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (83 reviews)
"Great place, great location."
United States
James H.
The price is NZ$607
includes taxes & fees
26 July - 27 July
New Seabury Cape Condo + Pool & Beach Escape

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 reviews)
"Great place to stay in Oak Bluffs"
United States
Stephen S.
The price is NZ$1,322
includes taxes & fees
21 July - 22 July
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is NZ$466
includes taxes & fees
15 July - 16 July
Charming studio in tranquil Falmouth with AC

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
West Tisbury
The price is NZ$1,594
includes taxes & fees
12 July - 13 July
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (93 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is NZ$1,047
includes taxes & fees
13 July - 14 July
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Welcoming 2-bedroom, 1-bath condo, AC in Oak Bluffs on Circuit Ave. 2nd floor.

Welcoming 2-bedroom, 1-bath condo, AC in Oak Bluffs on Circuit Ave. 2nd floor.
Oak Bluffs
The price is NZ$2,513
includes taxes & fees
3 July - 4 July
Welcoming 2-bedroom, 1-bath condo, AC in Oak Bluffs on Circuit Ave. 2nd floor.

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (15 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
The price is NZ$870
includes taxes & fees
27 July - 28 July
Small One Bedroom Private Cottage on Large Quiet Property.

LUX on Main | Downtown | Parking | Sleeps 8, #202

LUX on Main | Downtown | Parking | Sleeps 8, #202
Falmouth
The price is NZ$1,950
includes taxes & fees
6 July - 7 July
LUX on Main | Downtown | Parking | Sleeps 8, #202

The Sky-High Beach House: Panoramic Waterfront views

The Sky-High Beach House: Panoramic Waterfront views
Fairhaven
The price is NZ$888
includes taxes & fees
14 July - 15 July
The Sky-High Beach House: Panoramic Waterfront views

Modern Cape Cod home in vibrant beach community - steps to beach; pool access!!

Modern Cape Cod home in vibrant beach community - steps to beach; pool access!!
Falmouth
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful home in a great area!"
United States
Jillian P.
The price is NZ$5,095
includes taxes & fees
25 July - 26 July
Modern Cape Cod home in vibrant beach community - steps to beach; pool access!!

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.6 out of 10, Exceptional, (48 reviews)
"A wonderful home in a fabulous setting. The home has spacious & well laid out with a variety of beautiful outdoor spaces. Comfortable, with sufficient spaces inside and out; everyone had space to enjoy the property. We stayed for a week and never tired of the outdoor views. Convenient to great shopping and excellent beaches."
United States
Eric S.
The price is NZ$2,476
includes taxes & fees
3 July - 4 July
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette
Falmouth
8.4 out of 10, Very good, (29 reviews)
"Very nice location in North Falmouth where things feel timeless. The only disadvantage was there is no living/sitting room. You can sit in the kitchen or be in the bedrooms. Host was attentive and available."
United States
Michelle
The price is NZ$736
includes taxes & fees
7 July - 8 July
Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Westport
9.8 out of 10, Exceptional, (47 reviews)
"Super quiet and private neighborhood which makes for great walks!"
United States
Caitlin J.
The price is NZ$678
includes taxes & fees
13 July - 14 July
Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill

Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill
Falmouth
The price is NZ$3,162
includes taxes & fees
30 July - 31 July
Spacious Cape Cod Escape • Stoney Beach, Ferry & Shining Sea Bikeway.Bike.Grill

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, (1 review)
"I can’t say enough about this beautiful property. pictures don’t do any justice for this piece of heaven. The flowers were everywhere , it’s so apparent that the property owners take such pride in this beautiful property. The place was spotless when we walked in the door. We met the owners on arrival , they surprised us with a beautiful ballon to celebrate my 50th birthday. My family enjoyed the pool and the fun Tiki. The outdoor fireplace was inviting after the sun went down. I was a little...
United States
Miriam D.
The price is NZ$7,643
includes taxes & fees
23 July - 24 July
Beautiful Estate with salt water pool & pond with kayaks

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (26 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is NZ$2,293
includes taxes & fees
29 July - 30 July
The Seashell Cove - Martha's Vineyard

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Oak Bluffs
9.2 out of 10, Wonderful, (5 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 NZ$4,627
includes taxes & fees
1 Aug - 2 Aug
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!

Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!
Katama
The price is NZ$2,163
includes taxes & fees
15 July - 16 July
Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.4 out of 10, Exceptional, (13 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is NZ$1,670
includes taxes & fees
7 July - 8 July
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
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$736 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 69 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.