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Chilmark Holiday Rentals

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Check prices for these dates

Tonight
28 Dec - 29 Dec
Tomorrow
29 Dec - 30 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Chilmark holiday rentals

Outdoor pool, a heated pool
Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool
Chilmark
9.6 out of 10, Exceptional, (21)
"We loved this property and would love to return!"
United States
Clifford L.
The price is HK$2,063
HK$3,277 total
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy efficiency apartment/heated pool
Private beach nearby, beach bar
The Club at New Seabury

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (341)
"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 Club at New Seabury
On the beach, white sand
InnSeason Resorts Captain's Quarters

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
The price is HK$1,007
HK$1,153 total
includes taxes & fees
1 Jan - 2 Jan 2026
InnSeason Resorts Captain's Quarters
Marina
Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
2.0 star property
Dartmouth
10.0 out of 10, Exceptional, (11)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is HK$1,679
HK$3,047 total
includes taxes & fees
2 Jan - 3 Jan 2026
Charming cottage overlooking the bay in Padanaram Village.
Indoor pool, outdoor pool, pool loungers
Sea Mist Resort

Sea Mist Resort

Sea Mist Resort
3.0 star property
Mashpee
8.6 out of 10, Excellent, (144)
"Just there for one night but very enjoyable stay."
United States
Shawna
Sea Mist Resort
Beach
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (8)
"This property was beautiful! The hosts were excellent and were always available to message. I would recommend a stay at this home."
United States
Lisa Mason D.
The price is HK$1,438
HK$4,278 total
includes taxes & fees
16 Jan - 17 Jan 2026
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Outdoor dining
Newly Renovated Martha's Vineyard Vacation Rental!

Newly Renovated Martha's Vineyard Vacation Rental!

Newly Renovated Martha's Vineyard Vacation Rental!
Katama
9.6 out of 10, Exceptional, (47)
"We really enjoyed our stay. The house was conveniently located near Edgartown and South Beach in a quiet neighborhood. The house had everything we needed and more and was in great shape. Would definitely stay here again. "
United States
Patrick S.
The price is HK$1,574
HK$4,839 total
includes taxes & fees
30 Dec - 31 Dec
Newly Renovated Martha's Vineyard Vacation Rental!
Fridge, microwave, oven, stovetop
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

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (211)
"Nicely furnished and very comfortable. Very private, yet convenient location. "
United States
John H.
The price is HK$1,259
HK$3,842 total
includes taxes & fees
4 Jan - 5 Jan 2026
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Exterior
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!

Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
New Seabury
10.0 out of 10, Exceptional, (79)
"We were extremely happy with our stay. The condo was beautiful, had everything we needed. Looking forward to coming back again next year for a longer stay"
United States
Beth H.
The price is HK$1,146
HK$3,100 total
includes taxes & fees
31 Dec - 1 Jan 2026
Sleeps 6 @ New Seabury w/ Pool - All Season Modern Condo!
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.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
East Falmouth
10.0 out of 10, Exceptional, (88)
"This is an excellent home well-kept great location, and the Host is easy to communicate with. "
United States
Gary B.
The price is HK$2,273
HK$6,853 total
includes taxes & fees
3 Jan - 4 Jan 2026
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Exterior
Falmouth Oasis

Falmouth Oasis

Falmouth Oasis
2.0 star property
Falmouth
The price is HK$1,119
HK$3,380 total
includes taxes & fees
30 Dec - 31 Dec
Falmouth Oasis
Terrace/patio
The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (24)
"Property was perfectly kept and very comfortable. "
United States
Steve D.
The price is HK$1,943
HK$4,462 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Seashell Cove - Martha's Vineyard
Exterior
The Beach Estate, Panoramic Ocean Views, 5700 sqft

The Beach Estate, Panoramic Ocean Views, 5700 sqft

The Beach Estate, Panoramic Ocean Views, 5700 sqft
Mattapoisett
9.8 out of 10, Exceptional, (8)
"This was the perfect getaway for our large family. Everything was immaculate and we had all the comforts of home. We had a great week!"
United States
Catherine T.
The price is HK$5,491
HK$14,043 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Beach Estate, Panoramic Ocean Views, 5700 sqft
TV, fireplace, books
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

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)
"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$2,720
HK$6,944 total
includes taxes & fees
30 Dec - 31 Dec
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
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

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Oak Bluffs
9.4 out of 10, Exceptional, (88)
"Very happy. Thank you for the stay."
United States
Gillian S.
The price is HK$2,098
HK$3,845 total
includes taxes & fees
30 Dec - 31 Dec
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View
Fridge, microwave, oven, stovetop
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!

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)
"The house is clean, peaceful and perfectly appointed with everything you need for a great week on the Vineyard."
United States
Celeste P.
The price is HK$3,886
HK$8,429 total
includes taxes & fees
30 Dec - 31 Dec
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

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$4,274
HK$9,418 total
includes taxes & fees
30 Dec - 31 Dec
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior
Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!
2.5 star property
Falmouth
The price is HK$4,721
HK$11,256 total
includes taxes & fees
13 Jan - 14 Jan 2026
Cape Cod Escape at Casa de Leo!
Fridge, microwave, oven, stovetop
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach

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)
"Nice house! Great area. Close to nice beach !"
United States
Cally G.
The price is HK$4,889
HK$8,877 total
includes taxes & fees
30 Dec - 31 Dec
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
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

10/10 Excellent
"Very clean, easy, great location, comfortable."
Marcia 2-night trip
Posted 2 days 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:

  • 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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Chilmark is located in the city centre, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 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.