Photo by Shobha George

Chilmark Holiday Rentals

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Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Holiday Rentals in Chilmark

Beach
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

Chilmark
7.4 out of 10, Good, (6)
"This place is a nightmare!"
United States
Daniel K.
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Private beach nearby, beach bar
The Club at New Seabury

The Club at New Seabury

3.5 star property
Mashpee
9.0 out of 10, Wonderful, (338)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The price is HK$1,144
HK$1,310 total
includes taxes & fees
1 Dec - 2 Dec
The Club at New Seabury
Indoor pool, outdoor pool, pool loungers
Sea Mist Resort

Sea Mist Resort

3.0 star property
Mashpee
8.6 out of 10, Excellent, (141)
"Overall was a wonderful stay. Unit could use a hair dryer."
United States
Susan
Sea Mist Resort
5 bedrooms, desk, iron/ironing board, travel cot
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, (88)
"Great stay! "
United States
Michael M.
The price is HK$2,639
HK$7,421 total
includes taxes & fees
17 Dec - 18 Dec
Coastal chic meets French Provençal in this newly renovated oceanfront home.
On the beach, white sand
InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters

3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
InnSeason Resorts Captain's Quarters
Outdoor dining
Newly Renovated Near Amazing Sunset Beach

Newly Renovated Near Amazing Sunset Beach

Falmouth
9.8 out of 10, Exceptional, (73)
"Great stay"
United States
Michael S.
Newly Renovated Near Amazing Sunset Beach
Seasonal outdoor pool
Beachside Village Resort

Beachside Village Resort

3.0 star property
Falmouth
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort
Terrace/patio
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome

West Tisbury
9.0 out of 10, Wonderful, (35)
"Great spot for a get away. Private with easy access to activities."
United States
Philip E.
Uniquely designed island retreat with fast WiFi & private W/D - dogs welcome
Exterior
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs
6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Beach nearby, sun-loungers, beach towels
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth Heights
10.0 out of 10, Exceptional, (187)
"Great house with 4 bedrooms, good for couples. Walking distance to many places in Falmouth. Really enjoyed our stay here. Would stay again. "
United States
christine d.
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
On the beach
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

Mashpee
9.6 out of 10, Exceptional, (95)
"The beach is perfect for family fun in the sun, with many options for playing in the sand or water. The beds are comfortable, and having a washer and dryer was very helpful after a long day of water fun. The kitchen was adequate. "
United States
Linda D.
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!
Exterior
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

East Falmouth
10.0 out of 10, Exceptional, (112)
"The location and amenities were perfect. We are looking forward to returning next year."
United States
Trayce H.
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Terrace/patio
Stones Throw Waterfront

Stones Throw Waterfront

Dartmouth
8.8 out of 10, Excellent, (6)
"Great property very close to shops and restaurants in Padanaram. Very clean with lots of kitchen amenities. The portable AC units worked perfectly throughout the heatwave during our stay. Very quiet and peaceful location. We used the paddle boards and kayaks which was a nice bonus. It’s tricky getting them in the water especially at low tide."
United States
Becky S.
The price is HK$2,767
HK$5,021 total
includes taxes & fees
22 Nov - 23 Nov
Stones Throw Waterfront
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)
"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$4,281
HK$9,434 total
includes taxes & fees
21 Nov - 22 Nov
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Fridge, microwave, oven, stovetop
The quintessential MV home. Now booking for 2026!

The quintessential MV home. Now booking for 2026!

Oak Bluffs
9.8 out of 10, Exceptional, (55)
"Just a quick 4 minute drive to downtown. Listing was accurate and place was clean!"
United States
Jennifer D.
The quintessential MV home. Now booking for 2026!
Smart TV, fireplace, table football, ping pong
Sleeps 12, amazing view, tennis court, basketball court, beaches

Sleeps 12, amazing view, tennis court, basketball court, beaches

Edgartown
9.6 out of 10, Exceptional, (40)
"Great family friendly home with lots of living space and activities such as tennis, pickle ball, ping pong, and games all on the property. My family of 10, inclusive of 4 grandchildren had an awesome time."
United States
Bob B.
Sleeps 12, amazing view, tennis court, basketball court, beaches
Beach
Cozy getaway in a central location w/ a full kitchen & furnished deck

Cozy getaway in a central location w/ a full kitchen & furnished deck

Oak Bluffs
6.6 out of 10, (25)
"The furniture and amenities provided were good"
United States
Joseph T.
Cozy getaway in a central location w/ a full kitchen & furnished deck
Property grounds
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.

Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.

Falmouth Heights
10.0 out of 10, Exceptional, (53)
"Beautiful home in a great location! "
United States
Maurice R.
Classic Cape Cod - Ocean Views - Steps to Falmouth Heights Beach.
Interior
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach

Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach

2.0 star property
Falmouth
10.0 out of 10, Exceptional, (1)
"The location was great and the pullouts were comfortable. The only downside is the walk through bathroom."
United States
Matthew
Renovated One Bedroom Apartment Downtown Falmouth Minutes From the Beach
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)
"Awesome view"
United States
Dave B.
The price is HK$2,102
HK$3,878 total
includes taxes & fees
21 Nov - 22 Nov
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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

Inn on the Square

Inn on the Square

10/10 Excellent
"Convenient to all the shops and restaurants on main st"
Karen 1-night trip
Posted 3 days ago
Inn on the Square

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
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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?

Newly Renovated Near Amazing Sunset Beach: This holiday home rental outside of Chilmark offers a patio, a garden and a BBQ to help you feel perfectly comfortable 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 and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals are there in Chilmark?

Choose from 76 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 Lucy Vincent Beach 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.