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

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 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, (154 reviews)
"Cute, compact, and had everything we needed for ourstay. I'd definitely stay there again."
United States
Karen C.
The price is £376
includes taxes & fees
2 Sept - 3 Sept
Make Lasting Memories In This Adorable Vineyard Cottage!
Terrace/patio

2. 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 £387
includes taxes & fees
24 Aug - 25 Aug
Charming cottage overlooking the bay in Padanaram Village.
Terrace/patio

3. WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (52 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is £1,061
includes taxes & fees
20 Aug - 21 Aug
WATERFRONT Downtown Cottage w/ Beach
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, (38 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is £794
includes taxes & fees
6 Sept - 7 Sept
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Exterior

5. Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Falmouth
9.4 out of 10, Exceptional, (3 reviews)
"Good location, close to ferry and restaurants. Quiet neighborhood."
United States
Kerry B.
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
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

8/10 Good
"C"
Kayin 2-night trip
Posted 1 hour ago
Falmouth Inn

Find out more about Chilmark

Chilmark Cottages information

Number of reviews
108
Accommodation
153 Cottages
Lowest Price
£376
Highest Price
£1,061

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between £376 and £1,061 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.