Photo by Wen C.

Search Vacation Homes in Chilmark

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 979 Vacation Homes in Chilmark with updated reviews, rates, and availability.

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

2.0 star property
6.0 out of 10, (1)
"House needs some TLC! Lots of potential! Would have been nice to have a welcome binder with instructions on the home. Was disappointing from the listing. Not all expected equipment worked in the house. Curb appeal was poor and could be greatly improved with painting front door and a good day of landscaping. Cleanliness could have been better!"
Spacious home near the beach with deck, W/D, AC, & central location

Newly Renovated Martha's Vineyard Vacation Rental!

9.8 out of 10, Exceptional, (42)
"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 1,286
AED 2,979 total
includes taxes & fees
15 Jun - 16 Jun
Newly Renovated Martha's Vineyard Vacation Rental!

STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

2.0 star property
10.0 out of 10, Exceptional, (7)
"This beach town home is elegant and charming. The location is unbeatable; we enjoyed easy access to the beach, as well as nearby shops and restaurants. We spent our days beaching it up, and exploring the local area (all fun stuff within walking distance). From the moment we booked to the day we departed, the host always had prompt, friendly and helpful communication, and provided us with great recommendations for things to do for the whole family. THANK YOU FOR AN UNFORGETTABLE vacation, we just...
The price is AED 2,938
AED 4,801 total
includes taxes & fees
28 Jun - 29 Jun
STEP DIRECTLY ONTO YOUR PRIVATE MAUSHOP VILLAGE BEACH AT THIS SEASIDE TOWNHOME

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

6.0 out of 10, (19)
"This property is quite dated, with older furniture and finishes (paint was constantly peeling off the coffee table, old carpeting, etc.). There was also an unpleasant odor coming from the sink through our whole stay. Important to note that the property is not really walkable to Oak Bluffs or any beaches without walking on very busy roads (riding bikes to Oak Bluffs was a pretty easy trip). Overall, there are better options on MV for this price point."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (193)
"Wonderful location for Main Street shops/restaurants and a short drive to the beach. The bedrooms are spacious and the backyard is great. "
The price is AED 1,260
AED 2,686 total
includes taxes & fees
22 Jun - 23 Jun
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

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

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

9.6 out of 10, Exceptional, (85)
"Wish it was warmer lol stayed and it snowed "
Beachfront On John's Pond, Indoor HEATED Pool, and Dock!

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

9.6 out of 10, Exceptional, (16)
"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

Updated house close to town and beach with patio, AC, and games

2.0 star property
10.0 out of 10, Exceptional, (3)
"Great location, walking distance to beach, restaurants and shops!"
Updated house close to town and beach with patio, AC, and games

Historic Home with Gorgeous Antiques & Mondern Conveniences

6.4 out of 10, (18)
"Walking distance to beach, ferry, and town"
Historic Home with Gorgeous Antiques & Mondern Conveniences

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.

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

8.0 out of 10, Very Good, (3)
"This small house provided a big relief in our trip. Located steps from the best lobster roll in town and about a block from the water, this is a FANTASTIC spot for getting away."
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK

Island bliss located near shops and eateries-several island beaches also nearby

9.0 out of 10, Wonderful, (30)
"The cottage was perfect for our 4 day stay. Comfortable bedroom and relaxing living room. The street where the house is located is quiet and peaceful. We will be back."
Island bliss located near shops and eateries-several island beaches also nearby

Near Beaches & Trails: Home in East Falmouth

Near Beaches & Trails: Home in East Falmouth

Inviting dog-friendly home with furnished deck & firepit, near golf

9.8 out of 10, Exceptional, (14)
"House was just right, clean and convenient."
Inviting dog-friendly home with furnished deck & firepit, near golf

The Vienyard Haven Hideaway Apt

9.6 out of 10, Exceptional, (4)
"The property is clean and spacious. Great location and quiet."
The Vienyard Haven Hideaway Apt

Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8

Newly renovated 2BR house, FREE CAR w/beach sticker, pet friendly, sleeps 8

Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

8.8 out of 10, Excellent, (57)
"Good location. Would stay again."
Newly built bayview home, steps to dock/launch on Great Pond - small dogs OK

Dog-friendly Bournes Pond home minutes to downtown Falmouth with grill

9.2 out of 10, Wonderful, (11)
"Kitchen was great."
Dog-friendly Bournes Pond home minutes to downtown Falmouth with grill

Peaceful and Relaxing Cape Cod Ranch located 7 Min. from the Beach.

10.0 out of 10, Exceptional, (12)
"had a great weekend at the house and the area... might be back again"
Peaceful and Relaxing Cape Cod Ranch located 7 Min. 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.
Save an average of 15% on thousands of hotels when you're signed in