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

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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

A wooden deck with a white railing, two chairs, and a small table.

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 NZ$817
includes taxes & fees
2 Sept - 3 Sept
Make Lasting Memories In This Adorable Vineyard Cottage!
A sandy beach with a bench, a signpost, and a view of the ocean.

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 NZ$778
includes taxes & fees
6 Sept - 7 Sept
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
A wooden deck with Adirondack chairs and a table, surrounded by potted plants and overlooking a body of water.

3. Charming cottage overlooking the bay in Padanaram Village.

Charming cottage overlooking the bay in Padanaram Village.
Dartmouth
10.0 out of 10, Exceptional, (16 reviews)
"This property was beautiful, peaceful, and so relaxing! The communication and check-in were effortless, the house was spotless, and the views were fabulous! We definitely want to return!"
United States
Judith M.
The price is NZ$908
includes taxes & fees
10 Sept - 11 Sept
Charming cottage overlooking the bay in Padanaram Village.
A wooden deck with wicker furniture, a table with a vase of flowers, and a view of a marina with boats.

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 NZ$2,324
includes taxes & fees
8 Sept - 9 Sept
WATERFRONT Downtown Cottage w/ Beach
A residential property with a stone staircase leading to a wooden door, surrounded by well-maintained grass and shrubs.

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 NZ$1,801
includes taxes & fees
6 Sept - 7 Sept
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
A wooden deck with a table and chairs, a red umbrella, and a view of the water.

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.
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.
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Top Chilmark Hotel Reviews

Summercamp

Summercamp

10/10 Excellent
"Summer Camp is an awesome choice for a short stay or a week. Convenient to everything. I would definitely stay again."
Andrea 3-night trip
Posted 4 hours ago
Summercamp

Find out more about Chilmark

Chilmark Cottages information

Number of reviews
317
Accommodation
157 Cottages
Lowest Price
NZ$778
Highest Price
NZ$2,324

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between NZ$778 and NZ$2,324 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.
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.