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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 928 Vacation Homes in Chilmark with updated reviews, rates, and availability.

Coastal chic meets French Provençal in this newly renovated oceanfront home.
5 bedrooms, desk, iron/ironing board, travel crib

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (81)
"Great stay! "
The price is AED 1,928
AED 4,418 total
includes taxes & fees
4 Jun - 5 Jun
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
2 bedrooms, iron/ironing board, internet, bed sheets

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

9.0 out of 10, Wonderful, (11)
"Private with beach access minutes away."
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Fridge, microwave, oven, stovetop

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

9.6 out of 10, Exceptional, (49)
"This was a lovely home in a very nice location"
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Terrace/patio

Historic Oak Bluffs home, short walk to town, beach, and harbor.

9.6 out of 10, Exceptional, (28)
"We enjoy it all. "
Historic Oak Bluffs home, short walk to town, beach, and harbor.
Gorgeous Spacious Victorian Cape Code Beach View Retreat
Beach nearby

Gorgeous Spacious Victorian Cape Code Beach View Retreat

Gorgeous Spacious Victorian Cape Code Beach View Retreat
Charming coastal home with large yard, firepit, & grill - pool and beach access
Beach

Charming coastal home with large yard, firepit, & grill - pool and beach access

9.6 out of 10, Exceptional, (15)
"Our family was so impressed with this house! Every single element was thought of- the location was perfect and it was such a lovely stay. We hope to be back!"
Charming coastal home with large yard, firepit, & grill - pool and beach access
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Beach nearby, sun loungers, beach towels

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

10.0 out of 10, Exceptional, (168)
"Great house and location for stay during winter hockey tournament "
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC
Terrace/patio

Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC

9.8 out of 10, Exceptional, (8)
"The villa is well maintained and very clean. My stay was perfectly uneventful as I hoped it would be. Comfy accommodations, and conveniently located near to Mashpee Commons. The beach is a two minute walk, the property is lovely. "
Coastal townhome with easy beach access, beach gear, balconies, grill, W/D, & AC
Large New Seabury Home with Heated Pool and Hot Tub
Interior

Large New Seabury Home with Heated Pool and Hot Tub

10.0 out of 10, Exceptional, (41)
"Love the location and house is great! Lots of room to relax with the family"
Large New Seabury Home with Heated Pool and Hot Tub
Harbor Landing Resort
Exterior

Harbor Landing Resort

10.0 out of 10, Exceptional, (1)
"The kitchen facilities and out door grills made the vacation affordable. Not fancy, but very clean rooms. Would stay again for sure. Li"
Harbor Landing Resort
Our House in West Falmouth | House in Falmouth with private beach access
Beach nearby

Our House in West Falmouth | House in Falmouth with private beach access

9.4 out of 10, Exceptional, (9)
"The house was clean, well-furnished and felt very much like home. It is located on a quiet, picturesque street just a short walk to a small private beach This property is a perfect choice for a famiky vacation."
Our House in West Falmouth | House in Falmouth with private beach access
Edgartown Village Home w/ Pool. 4bdrm / 3.5bth
Fridge, microwave, oven, stovetop

Edgartown Village Home w/ Pool. 4bdrm / 3.5bth

10.0 out of 10, Exceptional, (2)
"Great, clean and up to date house close to town! Pool was great. Bedrooms were large with each room having a bathroom which made staying with a large group, much easier."
Edgartown Village Home w/ Pool. 4bdrm / 3.5bth
Summer home with expansive deck & wonderful location for beachgoers
Fridge, microwave, stovetop, dishwasher

Summer home with expansive deck & wonderful location for beachgoers

6.6 out of 10, (17)
"The house was very cute, it was calming and peaceful and the view on the porch was just magnificent. I would definitely come back again!"
Summer home with expansive deck & wonderful location for beachgoers
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
Beach nearby

New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖

9.4 out of 10, Exceptional, (12)
"Perfect for a family of 5! Well equipped and great location. "
New Home close to Beach, Bike Path, and Sleeps 10! ☀️ 🏖
Newly Renovated Martha's Vineyard Vacation Rental!
Outdoor dining

Newly Renovated Martha's Vineyard Vacation Rental!

9.8 out of 10, Exceptional, (41)
"This place was great. A quality home with great spaces and nice furnishings. Jenny was incredibly accommodating and responsive. We had a low stress, wonderful time and would certainly come here again. "
The price is AED 1,102
AED 2,720 total
includes taxes & fees
12 May - 13 May
Newly Renovated Martha's Vineyard Vacation Rental!
2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock
Outdoor dining

2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock

10.0 out of 10, Exceptional, (16)
"Great house. Plenty of room for games, TV and cooking (and eating) a feast! Beautiful sunsets!"
2 Acre Waterfront Home Overlooking Waquoit Bay with Spa and Swim Dock
Spacious home near the beach with deck, W/D, AC, & central location
Beach

Spacious home near the beach with deck, W/D, AC, & central location

2.0 star property
Spacious home near the beach with deck, W/D, AC, & central location
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Dining

Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs

10.0 out of 10, Exceptional, (34)
"Great house in a great location! Very clean and well stocked with any kitchen supplies, towels, etc"
Charming, cozy spacious home within 1 mile walking distance to Oak Bluffs
Guest House In Edgartown
Exterior

Guest House In Edgartown

10.0 out of 10, Exceptional, (3)
"Everything was great! Very clean, loved the decor! Everything you would ever need in the kitchen. Bed was very comfortable. Porch was lovely with comfortable seating. Living room had a great TV. We ate in a lot and had everything we needed.. Difficult to find. Glad we arrived before it got dark! Very peaceful. Hated to leave"
Guest House In Edgartown
Great Vacation Place Just Steps From The Beach
Sun loungers

Great Vacation Place Just Steps From The Beach

9.8 out of 10, Exceptional, (26)
"Thank you for a perfect week! Everything was great!"
Great Vacation Place Just Steps From The 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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Other property types in Chilmark

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
2 bedrooms, iron/ironing board, internet, bed sheets

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

9.0 out of 10, Wonderful, (11)
"Private with beach access minutes away."
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
The Club at New Seabury
Private beach nearby, beach bar

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (317)
"Perfect little cottage!"
The price is AED 613
AED 701 total
includes taxes & fees
13 May - 14 May
The Club at New Seabury
InnSeason Resorts Captain's Quarters
On the beach, white sand

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (168)
"Very peaceful "
InnSeason Resorts Captain's Quarters
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.