Chilmark Holiday Rentals

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

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$2,350
HK$4,868 total
includes taxes & fees
1 Apr - 2 Apr
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
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$1,938
HK$3,381 total
includes taxes & fees
31 Mar - 1 Apr
Charming cottage overlooking the bay in Padanaram Village.
Exterior

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is HK$1,410
HK$3,881 total
includes taxes & fees
31 Mar - 1 Apr
Falmouth Oasis
Property grounds

Beachside Village Resort

Beachside Village Resort
3.0 star property
Falmouth
9.4 out of 10, Exceptional, (101 reviews)
"Wonderful location, nice staff!"
United States
Claire
The price is HK$7,669
HK$8,777 total
includes taxes & fees
7 Apr - 8 Apr
Beachside Village Resort
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$4,308
HK$9,492 total
includes taxes & fees
31 Mar - 1 Apr
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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, (214 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is HK$1,566
HK$4,285 total
includes taxes & fees
31 Mar - 1 Apr
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
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$1,167
HK$2,196 total
includes taxes & fees
31 Mar - 1 Apr
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
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, (88 reviews)
"Amazing location right in the heart of Oak Bluffs! Easy entry. Great balconies overlooking the ocean. Wonderful kitchen and great TV. Would absolutely stay here again!"
United States
Jenn S.
The price is HK$2,115
HK$3,884 total
includes taxes & fees
31 Mar - 1 Apr
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$2,741
HK$6,999 total
includes taxes & fees
31 Mar - 1 Apr
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
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$3,478
HK$6,439 total
includes taxes & fees
27 Apr - 28 Apr
The Seashell Cove - Martha's Vineyard
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$1,175
HK$1,793 total
includes taxes & fees
21 Apr - 22 Apr
Charming studio in tranquil Falmouth with AC
Pool

2BR Condo in Cape Cod w/ Patio & Laundry

2BR Condo in Cape Cod w/ Patio & Laundry
Mashpee
The price is HK$1,527
HK$1,993 total
includes taxes & fees
26 Apr - 27 Apr
2BR Condo in Cape Cod w/ Patio & Laundry
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$7,123
HK$11,929 total
includes taxes & fees
31 Mar - 1 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$4,927
HK$8,992 total
includes taxes & fees
31 Mar - 1 Apr
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Fridge, microwave, oven, stovetop

Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod

Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod
Falmouth
The price is HK$2,937
HK$5,746 total
includes taxes & fees
6 Apr - 7 Apr
Contemporary 4-bedroom ranch style home with AC in charming Falmouth, Cape Cod
Terrace/patio

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
United States
Damani B.
The price is HK$2,350
HK$5,249 total
includes taxes & fees
25 Apr - 26 Apr
Oak Bluffs - Quiet neighborhood
Living area

LUX on Main | Downtown | Parking | Sleeps 6, #201

LUX on Main | Downtown | Parking | Sleeps 6, #201
Falmouth
The price is HK$1,415
HK$5,411 total
includes taxes & fees
1 Apr - 2 Apr
LUX on Main | Downtown | Parking | Sleeps 6, #201
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$5,534
HK$8,316 total
includes taxes & fees
31 Mar - 1 Apr
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
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$2,115
HK$3,884 total
includes taxes & fees
31 Mar - 1 Apr
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
Living area

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

LUX on Main | Downtown | Parking | Sleeps 6, #203
Falmouth
The price is HK$1,415
HK$5,438 total
includes taxes & fees
31 Mar - 1 Apr
LUX on Main | Downtown | Parking | Sleeps 6, #203
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

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

6/10 Okay
"Beautiful house! The rooms were very clean and the location was great. There is no staff on site but it was relatively easy to contact people. The walls are very thin and you will hear every single thing happening around you. I love pet friendly places but there was a dog left in the room that cried for hours and when I tried contacting management about it no one ever replied. Parking is easy and overall it was a good experience. "
Frida Nohemi 2-night trip
Posted 3 hours ago
The Franklin Hotel Martha's Vineyard

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?

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 62 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 Squibnocket Pond 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.