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

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Check prices for these dates

In two weeks
25 Sep - 27 Sep
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Chilmark cottages

Cottage (2 Bedrooms) | Interior

1. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
3.0 star property
East Falmouth
The price is AED 643
AED 2,278 total
includes taxes & fees
5 Oct - 6 Oct
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
Property grounds

2. 4 Mi to Bristol Beach! Coastal Retreat w/ Pond

4 Mi to Bristol Beach! Coastal Retreat w/ Pond
East Falmouth
9.4 out of 10, Exceptional, (3 reviews)
"We had a wonderful stay at this charming New England home. The house was spotless, beautifully maintained, and full of character. It had all the comforts we needed, inviting spaces to relax in after exploring the area. The location was perfect—close to local shops, scenic spots, and great dining. Our host was friendly, responsive, and made us feel right at home. We honestly couldn’t have asked for a better experience, and we look forward to returning."
United States
Shaun G.
The price is AED 485
AED 2,333 total
includes taxes & fees
5 Oct - 6 Oct
4 Mi to Bristol Beach! Coastal Retreat w/ Pond
Beach nearby, sun loungers, beach umbrellas, beach towels

3. 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, (53 reviews)
"We had a great stay! The community the home is located in was so quiet. The place was so clean, you would not know it was pet friendly! Our hosts had everything we needed and then some, from extra dog supplies to books to keep our toddler occupied. And our hosts kept the check in, stay and check out instructions simple. We would definitely book this place again!"
United States
Shawn A.
3 Bedroom Cottage just steps to Private Beach! Pet Friendly!
Property grounds

4. 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, (42 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is AED 2,935
AED 3,746 total
includes taxes & fees
9 Sep - 10 Sep
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Outdoor dining

5. Chappy cottage with private beach

Chappy cottage with private beach
Edgartown
10.0 out of 10, Exceptional, (19 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
Terrace/patio

6. 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 AED 2,531
AED 3,935 total
includes taxes & fees
8 Sep - 9 Sep
WATERFRONT Downtown Cottage w/ Beach
Terrace/patio

7. 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 AED 1,157
AED 1,900 total
includes taxes & fees
10 Sep - 11 Sep
Charming cottage overlooking the bay in Padanaram Village.
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

Green Harbor Waterfront Lodging

Green Harbor Waterfront Lodging

8/10 Good
"Great location. Staff was very friendly and accommodating."
Nicole 2-night trip
Posted 1 hour ago
Green Harbor Waterfront Lodging

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between AED 2,278 and AED 2,278 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 vacations 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.