Photo by Wen C.

Holiday Homes in Chilmark

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Featured Holiday Homes in Chilmark

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
10.0 out of 10, Exceptional, (35)
"The location was a perfect fit for our needs. "
The price is AU$1,483
includes taxes & fees
28 Oct - 29 Oct
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
9.0 out of 10, Wonderful, (2)
"The house was lovely. Very clean and orderly. Beautiful back porch that we enjoyed very much. The beds were very comfortable. Our only complaint was the Master bathroom needs some updating. The shower head desperately needs to be changed and the lighting is extremely poor. Also, only 1 half size mirror on the whole first floor. Other than that, it was perfect."
The price is AU$1,041
includes taxes & fees
21 Oct - 22 Oct
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
Newly Renovated Martha's Vineyard Vacation Rental!
9.6 out of 10, Exceptional, (46)
"Stay was nice, property is very clean and in close distance to most everything. Just wish they had made the lack of towels and linens more obvious in the listing. "
The price is AU$970
includes taxes & fees
17 Oct - 18 Oct
Newly Renovated Martha's Vineyard Vacation Rental!
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!
10.0 out of 10, Exceptional, (17)
"Home was excellent. Well appointed and everything to make my stay comfortable. Thanks to the hosts and hope to stay again."
The price is AU$587
includes taxes & fees
2 Nov - 3 Nov
Quaint 1 Bed 1 bath private beach home. Long term renters welcome for winter!
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
9.8 out of 10, Exceptional, (21)
"We enjoyed our stay and recommend It. Delightful back yard and patio area and a very pleasant front porch."
The price is AU$679
includes taxes & fees
3 Nov - 4 Nov
☼ Westport Point ☼ beach house on 1/2 acre easy access to beach/historic village
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
10.0 out of 10, Exceptional, (203)
"Loved this spot. So easy to get to downtown and Surf Beach. It was fabulous and clean!"
The price is AU$795
includes taxes & fees
3 Nov - 4 Nov
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Great Harbors Summer Home
The price is AU$1,744
includes taxes & fees
28 Oct - 29 Oct
Great Harbors Summer Home
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
10.0 out of 10, Exceptional, (15)
"The house is beautiful and conveniently located. The host, Melissa, was accessible and super helpful. We thoroughly enjoyed our time here and hope to be back in the future."
The price is AU$1,724
includes taxes & fees
18 Oct - 19 Oct
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
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."
The price is AU$1,882
includes taxes & fees
20 Oct - 21 Oct
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Beautiful Estate with salt water pool & pond with kayaks
2.5 star property
The price is AU$6,219
includes taxes & fees
17 Oct - 18 Oct
Beautiful Estate with salt water pool & pond with kayaks
The Seashell Cove - Martha's Vineyard
9.8 out of 10, Exceptional, (23)
"Property was perfectly kept and very comfortable. "
The price is AU$1,114
includes taxes & fees
19 Oct - 20 Oct
The Seashell Cove - Martha's Vineyard
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
10.0 out of 10, Exceptional, (7)
"Nice house! Great area. Close to nice beach !"
The price is AU$1,583
includes taxes & fees
19 Oct - 20 Oct
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Coastal chic meets French Provençal in this newly renovated oceanfront home.
10.0 out of 10, Exceptional, (87)
"Great stay! "
The price is AU$1,942
includes taxes & fees
27 Oct - 28 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Stones Throw Waterfront
8.8 out of 10, Excellent, (6)
"We've selected this place for two main reasons - 1) Kayaks included, and 2) pets are welcome (at least, a dog - check the rules). Apart from the two kayaks, three standup boards (SUB) were also available. The property is located near a small cove, so it's perfect for SUB beginners, as there are no waves due to power motorboats, jet skis, etc. Note that launching the boats ISN'T a walk in the park. You'll have to deal with a narrow and relatively steep path, dealing with shrubs, rocks, and...
The price is AU$1,199
includes taxes & fees
27 Oct - 28 Oct
Stones Throw Waterfront
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
10.0 out of 10, Exceptional, (13)
"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."
The price is AU$2,090
includes taxes & fees
27 Oct - 28 Oct
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen
10.0 out of 10, Exceptional, (56)
"Lovely home in quiet up island area. Short drive to beaches."
The price is AU$2,907
includes taxes & fees
4 Nov - 5 Nov
Historic Captains House - Newly Renovated Primary Bathroom and Upgraded Kitchen
The Beach Estate, Panoramic Ocean Views, 5700 sqft
9.8 out of 10, Exceptional, (6)
"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!"
The price is AU$2,840
includes taxes & fees
4 Nov - 5 Nov
The Beach Estate, Panoramic Ocean Views, 5700 sqft
Beautiful Home in Falmouth Village
10.0 out of 10, Exceptional, (9)
"Amazing property! Suited our needs perfectly with all en suite bathrooms!! Hosts were very responsive, knowledgeable, and kind 3. Much appreciated the hospitality! We plan to book again!! "
The price is AU$2,150
includes taxes & fees
22 Oct - 23 Oct
Beautiful Home in Falmouth Village
Cape cod getaway Close to Old Silver
The price is AU$812
includes taxes & fees
21 Oct - 22 Oct
Cape cod getaway Close to Old Silver
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

Top Chilmark Hotel Reviews

Find out more about Chilmark

Chilmark Holiday Homes information

Number of reviews
481
Accommodation
909 Holiday Homes
Lowest Price
AU$587
Highest Price
AU$2,907

Explore a world of travel with Expedia