Chilmark Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Chilmark holiday rentals

Outdoor pool, a heated pool

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (21 reviews)
"We loved this property and would love to return!"
United States
Clifford L.
The price is HK$2,310
HK$3,700 total
includes taxes & fees
30 Apr - 1 May
Cozy efficiency apartment/heated pool
Interior

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, (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 HK$1,010
HK$1,954 total
includes taxes & fees
13 Apr - 14 Apr
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Interior

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
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 HK$2,009
HK$3,495 total
includes taxes & fees
17 Apr - 18 Apr
Charming cottage overlooking the bay in Padanaram Village.
Property grounds

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, (91 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 HK$2,349
HK$4,867 total
includes taxes & fees
13 Apr - 14 Apr
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Smart TV, books

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 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 HK$7,122
HK$12,084 total
includes taxes & fees
13 Apr - 14 Apr
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Outdoor dining

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 reviews)
"Great place"
United States
Aaron Q.
The price is HK$4,926
HK$8,928 total
includes taxes & fees
13 Apr - 14 Apr
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Interior

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 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 HK$4,307
HK$9,491 total
includes taxes & fees
13 Apr - 14 Apr
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Terrace/patio

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is HK$2,255
HK$5,763 total
includes taxes & fees
13 Apr - 14 Apr
Spring Escape in Hatchville – Sleeps 6 + Dogs!
Marina

Edgartown Designer Cottage between Town & Beach.

Edgartown Designer Cottage between Town & Beach.
Katama
10.0 out of 10, Exceptional, (24 reviews)
"Wonderful week in MV! The cottage had everything we needed and was a great location to bike into town or to the beach. Would love to come back and stay again!"
United States
Lauren B.
The price is HK$2,623
HK$5,152 total
includes taxes & fees
1 May - 2 May
Edgartown Designer Cottage between Town & Beach.
Exterior

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is HK$1,410
HK$3,872 total
includes taxes & fees
13 Apr - 14 Apr
Falmouth Oasis
Terrace/patio

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!

Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Edgartown
9.8 out of 10, Exceptional, (16 reviews)
"Overall great experience"
United States
Scott P.
The price is HK$5,533
HK$8,314 total
includes taxes & fees
13 Apr - 14 Apr
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Smart TV, DVD player

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (25 reviews)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is HK$3,563
HK$6,552 total
includes taxes & fees
25 Apr - 26 Apr
The Seashell Cove - Martha's Vineyard
Exterior

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 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 HK$3,915
HK$8,493 total
includes taxes & fees
1 May - 2 May
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Pool

2BR Condo in Cape Cod w/ Patio & Laundry

2BR Condo in Cape Cod w/ Patio & Laundry
Mashpee
The price is HK$1,605
HK$2,114 total
includes taxes & fees
26 Apr - 27 Apr
2BR Condo in Cape Cod w/ Patio & Laundry
Interior

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.

Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
Tisbury
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful view of the lagoon; ideal place for a couple or single. Leisurely walk to town and close to public transportation."
United States
Adrienne W.
The price is HK$1,644
HK$3,298 total
includes taxes & fees
19 Apr - 20 Apr
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
TV, fireplace, books

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 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 HK$2,741
HK$6,998 total
includes taxes & fees
13 Apr - 14 Apr
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Outdoor spa tub

Trendy Great Pond Escape! HotTub Open! Sleeps 9!

Trendy Great Pond Escape! HotTub Open! Sleeps 9!
Falmouth
10.0 out of 10, Exceptional, (13 reviews)
"Very happy with our stay and definitely would rebook again in the future. "
United States
Reed W.
Trendy Great Pond Escape! HotTub Open! Sleeps 9!
1 bedroom, iron/ironing board, Internet, bed sheets

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is HK$1,057
HK$1,613 total
includes taxes & fees
15 Apr - 16 Apr
Charming studio in tranquil Falmouth with AC
Smart TV

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, (88 reviews)
"The location of this property cannot be beat! Our second time staying here."
United States
Ashley S.
The price is HK$2,114
HK$3,875 total
includes taxes & fees
13 Apr - 14 Apr
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Smart TV, fireplace

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, (95 reviews)
"Beautiful home with close access to everything Falmouth has to offer. The property was clean, comfortable, and perfect for a relaxing vacation. We truly enjoyed our stay and would highly recommend this home to anyone looking for a peaceful getaway in a great location."
United States
Kacie G.
The price is HK$6,257
HK$12,180 total
includes taxes & fees
10 May - 11 May
Coastal chic meets French Provençal in this newly renovated oceanfront home.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chilmark Hotel Reviews

Sea Mist Resort

Sea Mist Resort

10/10 Excellent
"Yes, everything was great in the property and its surroundings."
Nilza 2-night trip
Posted 2 days ago
Sea Mist Resort

Find out more about Chilmark

Search for holiday rentals in Chilmark on Expedia! You can easily find your home rentals, villas, holiday apartments in Chilmark using one of the methods below:

  • View our selection of featured holiday rentals in Chilmark
  • Use the map to find apartments and other holiday homes in the Chilmark neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chilmark while they last

Look no further and take a look at our great range of rental properties in Chilmark!

Explore a world of travel with Expedia

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 65 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.