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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Chilmark

Frederick William House
Enjoy a classic design with a view of lush greenery from the large window, a dining table, comfortable chair, and cabinet with decorative items.

Frederick William House

3.5 star property
9.6 out of 10, Exceptional, (278)
"Wonderful stay! Close to access Main Street and other things we wanted to do. "
$221 nightly
The price is $253
Aug 26 - Aug 27
Total includes taxes and fees
Frederick William House
The Christopher, The Edgartown Collection
Stately two-story building with a central entrance and symmetrical facade, surrounded by well-maintained landscaping.

The Christopher, The Edgartown Collection

3.0 star property
9.8 out of 10, Exceptional, (220)
"Lovely little place. Great location!"
$524 nightly
The price is $585
Sep 1 - Sep 2
Total includes taxes and fees
The Christopher, The Edgartown Collection
Inn on the Sound
Enjoy a seaside patio with ocean views, outdoor tables, and wicker chairs.

Inn on the Sound

3.5 star property
9.8 out of 10, Exceptional, (205)
"Quiet, charming, nice breakfast, right across from beach"
$469 nightly
The price is $537
Aug 11 - Aug 12
Total includes taxes and fees
Inn on the Sound
Delano Homestead Bed & Breakfast
Traditional two-story home surrounded by lush greenery and a stone wall.

Delano Homestead Bed & Breakfast

3.0 star property
9.6 out of 10, Exceptional, (144)
"Lovely specious facility with a friendly inn keeper. Welcoming with heathy breakfast served in a beautiful dining room where FDR and his family once sat. "
$212 nightly
The price is $237
Aug 6 - Aug 7
Total includes taxes and fees
Delano Homestead Bed & Breakfast
The Palmer House Inn
Guests can enjoy a serene beach experience with calm waters and scenic views.

The Palmer House Inn

3.5 star property
9.6 out of 10, Exceptional, (175)
"Superb staff and bkfsts Wonderful porch"
$359 nightly
The price is $411
Sep 1 - Sep 2
Total includes taxes and fees
The Palmer House Inn
Relax by the sea! Bed & Breakfast room near Horseneck State Beach
Relax in a cozy outdoor space with a fire pit, wicker chairs, and tables.

Relax by the sea! Bed & Breakfast room near Horseneck State Beach

9.0 out of 10, Wonderful, (2)
"We have a group of 9 business owners in our forum that all wanted their own room. We rented the whole Inn! It was a great set up for our groups agenda. Great restaurants and oyster shack very close which was nice for a couple of our meals! Highly recommend this fun place. It was a great taste of Cape Cod history and culture! "
Relax by the sea! Bed & Breakfast room near Horseneck State Beach
Crocker Inn
Cozy attic bedroom with a sloped ceiling, featuring a comfortable bed and a patterned rug.

Crocker Inn

3.0 star property
Crocker Inn
The 1720 House
Relax on a wicker sofa with blue and white cushions, surrounded by a beautiful mural and natural light.

The 1720 House

2.5 star property
6.8 out of 10, (41)
"Overpriced dirty rundown great location"
The 1720 House
Narragansett House
Step up to this charming Victorian-style home, featuring a welcoming porch with white balustrades and a cozy seating area.

Narragansett House

2.5 star property
8.8 out of 10, Excellent, (47)
"very clean and very helpful staff. breakfast only continental not very good for celiacs. stairs not good for older people"
Narragansett House
Captain Lawrence Inn
Beach nearby

Captain Lawrence Inn

3.5 star property
9.0 out of 10, Wonderful, (64)
Captain Lawrence Inn
The Dexter
Deluxe Single Room | 1 bedroom, free WiFi

The Dexter

3.0 star property
The Dexter
The Little B&B in Aquinnah
Property grounds

The Little B&B in Aquinnah

2.0 star property
The Little B&B in Aquinnah
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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

10/10 Excellent
"Good location. Enjoyed private beach"
Endia 1-night trip
Posted 13 hours ago
Vineyard Harbor Motel - Private Beach

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Chilmark?
Prices for B&Bs in Chilmark often vary, but you can find a great deal from $237 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chilmark B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed and Breakfast in Chilmark?
The most popular time to book a B&B in Chilmark is during the summer months, particularly July, when the island comes alive with visitors eager to experience its stunning beaches and vibrant local culture. The peak season stretches from June to August, offering a wealth of outdoor activities, including hiking the picturesque trails of the nearby Manuel F. Correllus State Forest and enjoying the sun-soaked shores of Chilmark's renowned beaches.

During July, expect warm temperatures averaging in the mid-70s to low 80s Fahrenheit, creating an inviting environment for swimming, sailing, and exploring the charming coastal town. This lively season attracts families, couples, and adventure seekers who relish the rich atmosphere filled with art, music, and culinary delights.

For those looking to travel on a budget, consider visiting in October. This month provides a quieter experience, with milder temperatures and the chance to witness the beautiful fall foliage that transforms the island's landscape. It's a great opportunity for leisurely strolls along the beach or exploring the local art galleries without the summer crowds.
What is the difference between a Chilmark Bed and Breakfast and a hotel?
Every Chilmark B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chilmark B&Bs.