Holiday Homes in Chilmark

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Chilmark holiday homes

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 NZ$1,857
includes taxes & fees
4 Feb - 5 Feb
Spacious Coastal New Seabury Home - Kayak Launch Across Street! Walk to Beach
Terrace/patio

Oak Bluffs - Quiet neighborhood

Oak Bluffs - Quiet neighborhood
Oak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"perfect for our needs"
United States
Ed V.
The price is NZ$1,083
includes taxes & fees
5 Feb - 6 Feb
Oak Bluffs - Quiet neighborhood
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, (212 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 NZ$808
includes taxes & fees
4 Feb - 5 Feb
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Exterior

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is NZ$728
includes taxes & fees
4 Feb - 5 Feb
Falmouth Oasis
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 NZ$1,955
includes taxes & fees
4 Feb - 5 Feb
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Beach

Beautiful Home in Falmouth Village

Beautiful Home in Falmouth Village
Falmouth
10.0 out of 10, Exceptional, (10 reviews)
"Great house and good location. "
United States
Jeannie E.
Beautiful Home in Falmouth Village
Exterior

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 reviews)
"We had an amazing time at this beautiful home. Great, clean space to spend an evening visit with friends and family. Great location with easy access around the island. Would highly recommend! "
United States
Jennifer T.
The price is NZ$1,749
includes taxes & fees
5 Feb - 6 Feb
NEW! Renovated Family-Friendly Vineyard Haven Home, Close to town!
Terrace/patio

Spring Escape in Hatchville – Sleeps 6 + Dogs!

Spring Escape in Hatchville – Sleeps 6 + Dogs!
Falmouth
10.0 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay. Everything was clean and well kept. "
United States
Lynn S.
The price is NZ$1,190
includes taxes & fees
4 Feb - 5 Feb
Spring Escape in Hatchville – Sleeps 6 + Dogs!
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 NZ$1,425
includes taxes & fees
4 Feb - 5 Feb
A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!
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)
"The hosts are excellent people, great communicators who want VBRO guests to have an outstanding experience. Chappy is a wonderful retreat from the rest of the world. That is my only word of caution, it requires a ferry to eat out or shop. Otherwise this is a great place to read write meditate beach and let go of everyday worries. It has a higher price tag because your paying for a premium location, guest service experience and higher quality accomodation."
United States
SparkleCappy
The price is NZ$1,711
includes taxes & fees
4 Feb - 5 Feb
Charming Chappaquiddick Retreat: Steps from Private Beach & Edgartown's Best!
Interior

Cape Cod Escape at Casa de Leo!

Cape Cod Escape at Casa de Leo!
Falmouth
The price is NZ$2,437
includes taxes & fees
4 Feb - 5 Feb
Cape Cod Escape at Casa de Leo!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chilmark Hotel Reviews

Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven

10/10 Excellent
"Rooms clean. Staff was amazing making sure snow was cleared. "
Arthur 1-night trip
Posted 8 days ago
Hampton Inn by Hilton New Bedford/Fairhaven

Find out more about Chilmark

Chilmark Holiday Homes information

Number of reviews
293
Accommodation
887 Holiday Homes
Lowest Price
NZ$808
Highest Price
NZ$2,437