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

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Our top choices for Chilmark holiday rentals

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, (35 reviews)
"We were looking for a weekend away from home, and we're lucky to find this place available. We got great recommendations for places to eat nearby, and were able to enjoy the area. We'd stay here again!"
United States
Zachary S.
The price is £392
includes taxes & fees
15 Jul - 16 Jul
Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

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 £325
includes taxes & fees
26 Jul - 27 Jul
New Seabury Cape Condo + Pool & Beach Escape

The Sky-High Beach House: Panoramic Waterfront views

The Sky-High Beach House: Panoramic Waterfront views
Fairhaven
The Sky-High Beach House: Panoramic Waterfront views

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, (92 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 £471
includes taxes & fees
12 Jul - 13 Jul
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

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 £385
includes taxes & fees
27 Jul - 28 Jul
Small One Bedroom Private Cottage on Large Quiet Property.

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is £204
includes taxes & fees
29 Jun - 30 Jun
Charming studio in tranquil Falmouth with AC

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

Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels
Westport
9.6 out of 10, Exceptional, (45 reviews)
"Super quiet and private neighborhood which makes for great walks!"
United States
Caitlin J.
The price is £287
includes taxes & fees
5 Jul - 6 Jul
Beautiful 'Saltbox Cape Cod' with Water Views on 3 Levels

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 £732
includes taxes & fees
7 Jul - 8 Jul
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

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

Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette
Falmouth
8.2 out of 10, Very good, (28 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 £286
includes taxes & fees
30 Jun - 1 Jul
Near Old Silver Beach Falmouth-Two bedroom, private bathroom and kitchenette

Elisa's Cottage - Your Family Vacation Destination

Elisa's Cottage - Your Family Vacation Destination
Woods Hole
10.0 out of 10, Exceptional, (7 reviews)
"We enjoyed the proximity to Woods Hole and Falmouth and the added snack touches. "
United States
Stefanie G.
The price is £713
includes taxes & fees
29 Jun - 30 Jun
Elisa's Cottage - Your Family Vacation Destination

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 £533
includes taxes & fees
30 Jun - 1 Jul
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

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, (218 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
The price is £559
includes taxes & fees
30 Jun - 1 Jul
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

LUX on Main | Downtown | Parking | Sleeps 6, #203

LUX on Main | Downtown | Parking | Sleeps 6, #203
Falmouth
The price is £753
includes taxes & fees
1 Jul - 2 Jul
LUX on Main | Downtown | Parking | Sleeps 6, #203

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Falmouth
9.0 out of 10, Wonderful, (2 reviews)
"Good location, close to ferry and restaurants. Quiet neighborhood."
United States
Kerry B.
The price is £582
includes taxes & fees
5 Jul - 6 Jul
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

Charming Guesthouse | Walk to Beach | Downtown

Charming Guesthouse | Walk to Beach | Downtown
Falmouth
The price is £586
includes taxes & fees
30 Jun - 1 Jul
Charming Guesthouse | Walk to Beach | Downtown

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
10.0 out of 10, Exceptional, (1 review)
"Awesome place! Clean! Great communication! Clean and well stocked. A pleasure to deal with."
United States
Kelly H.
The price is £1,365
includes taxes & fees
19 Jul - 20 Jul
4-bedroom house in lovely Edgartown..Centrally located

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 £1,104
includes taxes & fees
3 Jul - 4 Jul
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

Chappy - Family Beach House

Chappy - Family Beach House
Edgartown
10.0 out of 10, Exceptional, (15 reviews)
"Sun-filled, comfortable, and perfectly located!"
United States
Carmin R.
The price is £1,024
includes taxes & fees
26 Jul - 27 Jul
Chappy - Family Beach House

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 £935
includes taxes & fees
14 Jul - 15 Jul
Book your stay for Summer 2026 in this charming 2-bedroom house in Edgartown!

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 £709
includes taxes & fees
12 Jul - 13 Jul
serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower
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 £286 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.