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
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chilmark cottages

Property grounds

1. Make Lasting Memories In This Adorable Vineyard Cottage!

Make Lasting Memories In This Adorable Vineyard Cottage!
Oak Bluffs
9.8 out of 10, Exceptional, (155 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is HK$1,961
HK$4,004 total
includes taxes & fees
2 Sept - 3 Sept
Make Lasting Memories In This Adorable Vineyard Cottage!
Beach

2. 3 Bedroom Cottage just steps to Private Beach! Pet Friendly!

3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Mattapoisett
9.6 out of 10, Exceptional, (52 reviews)
"The area was beautiful! We went mid August and the neighborhood had gorgeous flowers blooming everywhere. The beach area was private and so relaxing. Our pup loved exploring the doggy beach. Good area for restaurants too… we really enjoyed Turk’s!"
United States
Helen R.
The price is HK$1,961
HK$3,697 total
includes taxes & fees
6 Sept - 7 Sept
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Terrace/patio

3. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (15 reviews)
"Super location, very nice accommodations, very clean, modern and comfortable "
United States
Cathie K.
The price is HK$2,471
HK$4,109 total
includes taxes & fees
24 Aug - 25 Aug
Charming cottage overlooking the bay in Padanaram Village.
Terrace/patio

4. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (54 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is HK$7,765
HK$11,389 total
includes taxes & fees
8 Sept - 9 Sept
WATERFRONT Downtown Cottage w/ Beach
Property grounds

5. 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, (40 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is HK$6,659
HK$8,480 total
includes taxes & fees
6 Sept - 7 Sept
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Outdoor dining

6. Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (18 reviews)
"What a gorgeous location, my family and I had a wonderful time on Chappy, will definitely be back!"
United States
Clinton G.
The price is HK$7,059
HK$12,335 total
includes taxes & fees
23 Aug - 24 Aug
Chappy cottage with private 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.
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

Summercamp

Summercamp

10/10 Excellent
"Beautiful"
Camille Y 3-night trip
Posted 5 hours ago
Summercamp

Find out more about Chilmark

Chilmark Cottages information

Number of reviews
4,036
Accommodation
157 Cottages
Lowest Price
HK$955
Highest Price
HK$4,696

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between HK$955 and HK$4,696 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.

Explore a world of travel with Expedia