A dock with boats, a small wooden structure, and a forested shoreline.

Search Cottages 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
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Chilmark cottages

Property grounds

The Sky-High Beach House: Panoramic Waterfront views

The Sky-High Beach House: Panoramic Waterfront views
Fairhaven
The price is €440
includes taxes & fees
14 Jul - 15 Jul
The Sky-High Beach House: Panoramic Waterfront views
Property grounds

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (93 reviews)
The price is €540
includes taxes & fees
14 Jul - 15 Jul
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Exterior

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (15 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
The price is €454
includes taxes & fees
27 Jul - 28 Jul
Small One Bedroom Private Cottage on Large Quiet Property.
Terrace/patio

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (49 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is €1,225
includes taxes & fees
31 Jul - 1 Aug
WATERFRONT Downtown Cottage w/ Beach
Property grounds

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (34 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is €848
includes taxes & fees
14 Jul - 15 Jul
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Exterior

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Tisbury
10.0 out of 10, Exceptional, (58 reviews)
"We loved the location and place was great!"
United States
Eileen M.
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Exceptional location - quick walk to the VH ferry. Bus stops right outside the motel as well. Staff went above and beyond and the room decor was so cute!! Will def stay here again. Only thing that would put it over the top would be to get the outside shower working."
Colleen 1-night trip
Posted less than an hour ago
Vineyard Harbor Motel - Private Beach

Find out more about Chilmark

Chilmark Cottages information

Number of reviews
249
Accommodation
161 Cottages
Lowest Price
€440
Highest Price
€1,225

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between €440 and €1,225 per night for cottages in Chilmark. No matter your budget, a fantastic stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chilmark with Expedia?
We think that holidays should be a walk in the park, so if you're searching for cottages in Chilmark at an affordable price, Expedia can help. Keep the budget under control and pick a low-cost option far away from the city rush, or book a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Chilmark?
With Expedia's filter tool, sourcing cheap cottages in Chilmark is a snap. To find properties that'll make your wallet smile, narrow down your search by star rating, budget and amenities.
What is there to do in Chilmark near my cottage?
Whatever you're interested in, Chilmark has lots of things to keep you entertained. Menemsha Beach, Lucy Vincent Beach and The Yard are on many visitors' trip plans. Don't forget about Chilmark Chocolates, Waskosim's Rock Reservation and Fulling Mill Brook Preserve either. With Expedia's hotel deals in Chilmark, you'll be able to discover more neat attractions like these with the money you save.