Holiday Homes in Chilmark
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chilmark holiday homes
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1
Quaint 1 Bed 1 bath private beach home. Long term renter welcome Dec 1Dartmouth
10.0 out of 10, Exceptional, (17 reviews)
"Great location, clean house. Well stocked with supplies and beach items."
Tyler M.
The price is AU$497
includes taxes & fees
15 Mar - 16 Mar
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."
Swathanthra M.
The price is AU$1,650
includes taxes & fees
3 Mar - 4 Mar
The price is AU$678
includes taxes & fees
3 Mar - 4 Mar
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 BeachFalmouth
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!"
Annemarie G.
The price is AU$603
includes taxes & fees
3 Mar - 4 Mar
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! "
Jennifer T.
The price is AU$1,478
includes taxes & fees
3 Mar - 4 Mar
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning Views
Scenic 4BR/3BA Waterfront Getaway with private dock, kayaks & Stunning ViewsDartmouth
10.0 out of 10, Exceptional, (14 reviews)
"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."
Nick R.
The price is AU$1,949
includes taxes & fees
3 Mar - 4 Mar
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 "
Louis R.
The price is AU$1,213
includes taxes & fees
3 Mar - 4 Mar
Oak Bluffs - Quiet neighborhood
Oak Bluffs - Quiet neighborhoodOak Bluffs
9.4 out of 10, Exceptional, (43 reviews)
"Perfectly situated!"
Damani B.
The price is AU$930
includes taxes & fees
4 Mar - 5 Mar
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.
Find holiday rentals that suit your style
Private holiday homes
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Chilmark Hotel Reviews
Iris Hotel Cape Cod
10/10 Excellent
Find out more about Chilmark
Chilmark Holiday Homes information
Number of reviews | 361 |
|---|---|
Accommodation | 887 Holiday Homes |
Lowest Price | AU$497 |
Highest Price | AU$2,110 |
Explore a world of travel with Expedia
- Holiday Parks in Aquinnah
- Aquinnah Hotels
- Inns in Aquinnah
- Holiday Homes in Chappaquiddick Island
- Chappaquiddick Island Hotels
- Luxury Hotels in Edgartown
- Edgartown Hotels
- Inns in Edgartown
- Condo Rentals in Fairhaven
- Holiday Homes in Fairhaven
- B&B in Falmouth
- Caravan Parks in Falmouth
- Holiday Homes in Falmouth
- Beach Hotels in Falmouth
- Cheap Hotels in Falmouth
- Luxury Hotels in Falmouth
- Falmouth Hotels
- Motels in Falmouth
- Hotels near Inkwell Beach
- Beach Hotels in Katama
- Katama Hotels
- Hotels near Long Point Beach
- Hotels near Martha's Vineyard
- Apartments in Martha's Vineyard
- B&B in Martha's Vineyard
- Condo Rentals in Martha's Vineyard
- Cottages in Martha's Vineyard
- Country House in Martha's Vineyard
- Guest Houses in Martha's Vineyard
- Holiday Homes in Martha's Vineyard
- Hostels in Martha's Vineyard
- Beach Hotels in Martha's Vineyard
- Boutique Hotels in Martha's Vineyard
- Cheap Hotels in Martha's Vineyard
- Hotels with Pool in Martha's Vineyard
- Luxury Hotels in Martha's Vineyard
- Marriott Hotels & Resorts in Martha's Vineyard
- Spa Hotels in Martha's Vineyard
- Martha's Vineyard Hotels
- Lodges in Martha's Vineyard
- Resort in Martha's Vineyard
- Treehouses in Martha's Vineyard
- B&B in New Seabury
- B&B in Oak Bluffs
- Boutique Hotels in Oak Bluffs
- Lgbt Welcoming Hotels in Oak Bluffs
- Luxury Hotels in Oak Bluffs
- Oak Bluffs Hotels
- Inns in Oak Bluffs
- B&B in Seabrook
- Holiday Homes in Seabrook
- Motels in Seabrook
- Caravan Parks in Vineyard Haven
- Vineyard Haven Hotels
- West Tisbury Hotels
- Hotels near Woods Hole Ferry Terminal
- Woods Hole Hotels
- Lodges in Woods Hole
- Hotels near Woods Hole Terminal
- Town Houses in Woods Hole
- Flights to Dukes County
- Flights to Aquinnah
- Flights to Edgartown
- Flights to Falmouth
- Flights to Martha's Vineyard
- Flights to Martha's Vineyard
- Flights from New York to Martha's Vineyard
- Flights from Boston (BOS) to Vineyard Haven (MVY)
- Flights from New York (JFK) to Vineyard Haven (MVY)
- Flights from New York (LGA) to Vineyard Haven (MVY)
- Flights from Philadelphia (PHL) to Vineyard Haven (MVY)
- Avis Rental Cars in Martha's Vineyard
- Car hire in Avis 1870 W Broad St
- Car hire near Edgartown Beach
- Car hire Falmouth
- Rental cars Martha's Vineyard airport
- Car hire near Martha's Vineyard
- Car hire near Surf Drive Beach
- Car hire near The Yard
- Car hire near Vineyard Haven Terminal
- Car hire Vineyard Haven
- Car hire near Woods Hole Ferry Terminal
- Car hire Woods Hole
- Discount Car Rentals Rental Cars in Martha's Vineyard
- Enterprise Rental Cars in Martha's Vineyard
- Hertz Rental Cars in Martha's Vineyard
- Locauto Rental Cars in Martha's Vineyard
- Rent A Wreck Rental Cars in Martha's Vineyard