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

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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 NZ$873
includes taxes & fees
14 July - 15 July
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)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is NZ$1,042
includes taxes & fees
25 July - 26 July
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 NZ$868
includes taxes & fees
27 July - 28 July
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 NZ$2,396
includes taxes & fees
31 July - 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 NZ$1,649
includes taxes & fees
14 July - 15 July
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.
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Top Chilmark Hotel Reviews

Inn on the Square

Inn on the Square

8/10 Good
"perfect location , great staff . It only needs some newer furniture in the rooms but for an Inn it is really good."
Iulian 3-night trip
Posted less than an hour ago
Inn on the Square

Find out more about Chilmark

Chilmark Cottages information

Number of reviews
249
Accommodation
157 Cottages
Lowest Price
NZ$868
Highest Price
NZ$2,396

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between NZ$868 and NZ$2,396 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.