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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chilmark cottages

A covered outdoor area with a wooden deck, seating, and a view of the water.

1. Summercamp

Summercamp
3.5 star property
Oak Bluffs
9.4 out of 10, Exceptional, (1,010 reviews)
"Love this place!!!"
United States
Earl
The price is CA $291
CA $333 total
includes taxes & fees
Oct 29 - Oct 30
Summercamp
An aerial view of a residential area with houses, a river, and a parking lot.

2. The Coonamessett

The Coonamessett
3.5 star property
Falmouth
8.8 out of 10, Excellent, (704 reviews)
"Good restaurant."
United States
richard
The price is CA $134
CA $154 total
includes taxes & fees
Nov 2 - Nov 3
The Coonamessett
A covered porch with wicker furniture and a vase of flowers.

3. Lamberts Cove Inn

Lamberts Cove Inn
3.5 star property
Vineyard Haven
9.4 out of 10, Exceptional, (89 reviews)
"What a nice place, the staff and property were welcoming and such a nice slice of heaven!"
United States
Ashley
The price is CA $435
CA $486 total
includes taxes & fees
Oct 13 - Oct 14
Lamberts Cove Inn
A balcony with a table and chairs, overlooking a marina with boats and a distant shoreline.

4. Mansion House Inn And Spa

Mansion House Inn And Spa
3.5 star property
Vineyard Haven
9.4 out of 10, Exceptional, (1,000 reviews)
"Lovely place"
United States
Robyn
The price is CA $248
CA $298 total
includes taxes & fees
Nov 2 - Nov 3
Mansion House Inn And Spa
A patio with a wooden table and chairs, a hanging flower pot with red and yellow flowers, and a view of the sea with boats in the background.

5. Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach
2.5 star property
Vineyard Haven
9.0 out of 10, Wonderful, (820 reviews)
"Clean and had a nice beach access"
United States
Michael
The price is CA $250
CA $279 total
includes taxes & fees
Nov 11 - Nov 12
Vineyard Harbor Motel - Private Beach
A long dining table with a glass centerpiece, surrounded by chairs and a buffet setup.

6. Iris Hotel Cape Cod

Iris Hotel Cape Cod
3.0 star property
Falmouth
8.4 out of 10, Very good, (421 reviews)
"It was a perfect location for us, it was clean, updated and we slept great!"
United States
Jennie
The price is CA $184
CA $211 total
includes taxes & fees
Nov 1 - Nov 2
Iris Hotel Cape Cod
A large, two-story building with a stone facade, a prominent sign reading "Inn on the Square," and a patio area with outdoor seating.

7. Inn on the Square

Inn on the Square
3.5 star property
Falmouth
8.8 out of 10, Excellent, (1,001 reviews)
"This was a comfortable stay, quiet and convenient to shopping and dining"
United States
Jeanine
The price is CA $171
CA $232 total
includes taxes & fees
Oct 25 - Oct 26
Inn on the Square
A wooden dock extending into a body of water, with a building featuring a gabled roof and white trim.

8. Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel

Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel
3.0 star property
Edgartown
8.4 out of 10, Very good, (643 reviews)
"Enjoyed our stay, quiet, convenient to everything in Edgartown!"
United States
Lisa
The price is CA $257
CA $289 total
includes taxes & fees
Nov 1 - Nov 2
Edgar Hotel Martha's Vineyard, an Ascend Collection Hotel
A two-story house with a brick pathway leading to the front door, surrounded by a well-maintained lawn and green Adirondack chairs.

9. The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard
2.0 star property
Edgartown
9.2 out of 10, Wonderful, (217 reviews)
"Great place to stay. Very nice and private room. We stayed in room 19 and it had a private patio with a kitchenette in our room. Place was easy to find and had plenty of parking. Would recommend again"
United States
Alex
The price is CA $242
CA $270 total
includes taxes & fees
Nov 11 - Nov 12
The Franklin Hotel Martha's Vineyard
A Hampton Inn with a covered outdoor area, a parking lot, and well-maintained landscaping.

10. Hampton Inn by Hilton New Bedford/Fairhaven

Hampton Inn by Hilton New Bedford/Fairhaven
2.5 star property
Fairhaven
9.0 out of 10, Wonderful, (1,003 reviews)
"The facility was excellent and we had a nice stay"
United States
james
The price is CA $156
CA $175 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn by Hilton New Bedford/Fairhaven
A covered outdoor seating area with a white sofa, two wicker rocking chairs, and a round table.

11. Faraway Martha's Vineyard

Faraway Martha's Vineyard
4.0 star property
Edgartown
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff was great. Lovely and location excellent."
United States
Thomas
The price is CA $334
CA $391 total
includes taxes & fees
Nov 1 - Nov 2
Faraway Martha's Vineyard
A spacious outdoor seating area with sofas and chairs, a central table, and a view of the landscape.

12. AutoCamp Cape Cod

AutoCamp Cape Cod
4.0 star property
Falmouth
9.2 out of 10, Wonderful, (407 reviews)
"Great place to stay. Loved it."
United States
John
The price is CA $124
CA $199 total
includes taxes & fees
Oct 25 - Oct 26
AutoCamp Cape Cod
A large, multi-story house with a covered porch and a well-maintained lawn.

13. Shore Haven Inn

Shore Haven Inn
3.0 star property
Falmouth
9.6 out of 10, Exceptional, (255 reviews)
"Wonderful room and inn. Close to beach and town. Highly recommend"
United States
Mike
The price is CA $235
CA $276 total
includes taxes & fees
Oct 13 - Oct 14
Shore Haven Inn
A row of white lounge chairs with blue cushions, arranged under a white canopy, overlooking the sea.

14. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
The price is CA $210
CA $240 total
includes taxes & fees
Nov 1 - Nov 2
The Club at New Seabury
Exterior

15. Red Horse Inn

Red Horse Inn
2.5 star property
Falmouth Heights
9.2 out of 10, Wonderful, (650 reviews)
"Fabulous place to stay !"
United States
Thomas
The price is CA $241
CA $276 total
includes taxes & fees
Oct 12 - Oct 13
Red Horse Inn
A brick building with a sign for 'The Admiralty Inn' and a covered entrance.

16. Admiralty Inn & Suites - a Red Collection Hotel

Admiralty Inn & Suites - a Red Collection Hotel
3.0 star property
East Falmouth
8.6 out of 10, Excellent, (556 reviews)
"Great location and a great place to stay!"
United States
Toleeya
The price is CA $160
CA $201 total
includes taxes & fees
Nov 1 - Nov 2
Admiralty Inn & Suites - a Red Collection Hotel
A hotel with a well-maintained garden, a central fire feature, and a sign reading "Sea Crest".

17. Sea Crest Beach Resort

Sea Crest Beach Resort
3.5 star property
North Falmouth
7.6 out of 10, Good, (530 reviews)
"Clean Room,staff was ok"
United States
Michael
The price is CA $160
CA $265 total
includes taxes & fees
Nov 1 - Nov 2
Sea Crest Beach Resort
A deck with a wicker sofa, a table with a bottle of champagne, and a tray of snacks.

18. Harbor View Hotel

Harbor View Hotel
5.0 star property
Edgartown
8.8 out of 10, Excellent, (1,001 reviews)
"Top notch hotel!"
United States
Eryn
The price is CA $417
CA $503 total
includes taxes & fees
Oct 25 - Oct 26
Harbor View Hotel
A modern building with a covered entrance and a sign reading "Bar 3".

19. Falmouth Inn

Falmouth Inn
2.0 star property
Falmouth
8.0 out of 10, Very good, (1,000 reviews)
"Clean room, very friendly and helpful staff. This is a modest motel, but a great bargain."
United States
Robert G
The price is CA $164
CA $216 total
includes taxes & fees
Oct 20 - Oct 21
Falmouth Inn
A balcony with two lounge chairs, a small round table, and a view of the beach and ocean.

20. Morgan Hotel

Morgan Hotel
2.5 star property
Oak Bluffs
8.6 out of 10, Excellent, (271 reviews)
"Very well maintained and located close to shops and restaurants."
United States
Valerie
The price is CA $247
CA $283 total
includes taxes & fees
Nov 11 - Nov 12
Morgan Hotel
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
"Magical stay! This place was perfection for location… vibe…. Feel and moments."
Andre 1-night trip
Posted 4 hours ago
Summercamp

Find out more about Chilmark

Chilmark Cottages information

Number of reviews
5,406
Accommodation
141 Cottages
Lowest Price
CA $154
Highest Price
CA $503

Frequently asked questions

How much do cottages in Chilmark cost?
You can expect to pay between CA $154 and CA $503 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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