Chilmark Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Chilmark holiday rentals

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$4,866 total
includes taxes & fees
19 May - 20 May
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Interior

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

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.4 out of 10, Very good, (25 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$932
HK$1,891 total
includes taxes & fees
17 May - 18 May
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Private beach nearby, beach bar

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (355 reviews)
"Our stay was great and Amy at the front desk is a god send she was absolutely the best."
United States
Jasmine
The price is HK$1,815
HK$2,077 total
includes taxes & fees
17 May - 18 May
The Club at New Seabury
TV

New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (81 reviews)
"Host was super organized with clear instructions and easy check-in. The condo was well appointed and beautifully decorated. We enjoyed our brief stay!"
United States
Gina P.
The price is HK$768
HK$2,600 total
includes taxes & fees
21 May - 22 May
New Seabury Cape Condo + Pool & Beach Escape
Dining

Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6

Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6
Popponesset
10.0 out of 10, Exceptional, (188 reviews)
"great stay! fantastic location."
United States
Emily P.
The price is HK$2,341
HK$6,497 total
includes taxes & fees
17 May - 18 May
Waterfront Gem: Hot Tub, Fire Pit & Private Beach! 3 Bed, 1.5 Baths, Sleeps 6
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$2,008
HK$3,372 total
includes taxes & fees
18 May - 19 May
Charming cottage overlooking the bay in Padanaram Village.
Exterior

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is HK$1,409
HK$3,871 total
includes taxes & fees
18 May - 19 May
Falmouth Oasis
Interior

Brand new! Lovely apartment-Vineyard Haven

Brand new! Lovely apartment-Vineyard Haven
Tisbury
9.8 out of 10, Exceptional, (25 reviews)
"Lovely and all brand new accommodation's that are clean and comfy! A quiet location too! "
United States
Nancy K.
The price is HK$1,677
HK$3,544 total
includes taxes & fees
18 May - 19 May
Brand new! Lovely apartment-Vineyard Haven
Sun-loungers, beach towels

Charming Vacation Home in Oak Bluffs.

Charming Vacation Home in Oak Bluffs.
Oak Bluffs
The price is HK$2,812
HK$6,088 total
includes taxes & fees
26 May - 27 May
Charming Vacation Home in Oak Bluffs.
Beach nearby

Loft Hideaway in Falmouth Village

Loft Hideaway in Falmouth Village
Falmouth
9.6 out of 10, Exceptional, (4 reviews)
"We really enjoyed our visit!! The location can’t be beat and Falmouth was a great place to explore. "
United States
Nancy F.
The price is HK$1,389
HK$2,746 total
includes taxes & fees
16 May - 17 May
Loft Hideaway in Falmouth Village
Smart TV, DVD player

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 HK$4,758
HK$8,071 total
includes taxes & fees
19 May - 20 May
The Seashell Cove - Martha's Vineyard
Interior

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, (216 reviews)
"Great place to stay for Christmas with our family. Cozy place with a convenient location. "
United States
Gail B.
The price is HK$1,566
HK$4,275 total
includes taxes & fees
18 May - 19 May
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
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$1,622 total
includes taxes & fees
17 May - 18 May
Charming studio in tranquil Falmouth with AC
Marina

Edgartown Designer Cottage between Town & Beach.

Edgartown Designer Cottage between Town & Beach.
Katama
10.0 out of 10, Exceptional, (25 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$5,108 total
includes taxes & fees
19 May - 20 May
Edgartown Designer Cottage between Town & Beach.
TV, fireplace

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

LUX on Main | Downtown | Parking | Sleeps 6, #203
Falmouth
The price is HK$1,177
HK$5,084 total
includes taxes & fees
18 May - 19 May
LUX on Main | Downtown | Parking | Sleeps 6, #203
Exterior

4-bedroom house in lovely Edgartown..Centrally located

4-bedroom house in lovely Edgartown..Centrally located
Edgartown
The price is HK$1,762
HK$7,242 total
includes taxes & fees
21 May - 22 May
4-bedroom house in lovely Edgartown..Centrally located
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.
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

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 HK$3,347
HK$5,471 total
includes taxes & fees
16 May - 17 May
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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$2,740
HK$6,997 total
includes taxes & fees
16 May - 17 May
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Exterior

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$2,584
HK$4,495 total
includes taxes & fees
30 May - 31 May
Cozy studio with water views. AC,WiFi, full kitchen, private entrance and patio.
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

Mansion House Inn And Spa

Mansion House Inn And Spa

10/10 Excellent
"Great location"
Michael 1-night trip
Posted 8 hours ago
Mansion House Inn And Spa

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:

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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?

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool. : This holiday home rental outside of Chilmark is located near the beach, and has a patio, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 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 books.

How many holiday rentals are there in Chilmark?

Choose from 67 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.