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

Search Chilmark Cottage Rentals from CA $705

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Check prices for these dates

In two weeks
Jul 24 - Jul 26
In two months
Sep 4 - Sep 6
In three months
Oct 2 - Oct 4
In four months
Oct 30 - Nov 1

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 CA $339
CA $705 total
includes taxes & fees
Jul 14 - Jul 15
The Sky-High Beach House: Panoramic Waterfront views
Terrace/patio

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (50 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is CA $1,159
CA $1,750 total
includes taxes & fees
Jul 13 - Jul 14
WATERFRONT Downtown Cottage w/ Beach
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, (16 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 CA $425
CA $723 total
includes taxes & fees
Jul 27 - Jul 28
Small One Bedroom Private Cottage on Large Quiet Property.
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 CA $1,060
CA $1,353 total
includes taxes & fees
Jul 14 - Jul 15
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, (59 reviews)
"We loved the location and place was great!"
United States
Eileen M.
The price is CA $1,131
CA $1,443 total
includes taxes & fees
Jul 18 - Jul 19
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.
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Top Chilmark Hotel Reviews

Falmouth Inn

Falmouth Inn

10/10 Excellent
"Clean and well taken care of"
Chiara 4-night trip
Posted 5 hours ago
Falmouth Inn

Find out more about Chilmark

Chilmark Cottages information

Number of reviews
159
Accommodation
161 Cottages
Lowest Price
CA $705
Highest Price
CA $1,750

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between CA $705 and CA $1,750 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.
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.

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