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

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Chilmark bed & breakfast

A two-story house with a stone facade, a balcony, and a well-maintained garden.

1. Frederick William House

Frederick William House
3.5 star property
Falmouth
9.6 out of 10, Exceptional, (330 reviews)
"Loved the property and our room!"
United States
Kathy
$158 nightly
The price is $181
Nov 1 - Nov 2
Total with taxes and fees
Frederick William House
A two-story house with a front porch, a stone wall, and a well-maintained garden.

2. Delano Homestead Bed & Breakfast

Delano Homestead Bed & Breakfast
3.0 star property
Fairhaven
9.6 out of 10, Exceptional, (181 reviews)
"Beautiful home and friendly staff! Great breakfast"
United States
Richard
$150 nightly
The price is $168
Nov 1 - Nov 2
Total with taxes and fees
Delano Homestead Bed & Breakfast
A cozy room with wicker furniture, a stone fireplace, and a view of the ocean.

3. Inn on the Sound

Inn on the Sound
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (232 reviews)
"It was a great place to stay!"
United States
Dustin
$339 nightly
The price is $388
Oct 25 - Oct 26
Total with taxes and fees
Inn on the Sound
An outdoor patio with a fire table, seating, and a table set for a meal.

4. The Palmer House Inn

The Palmer House Inn
3.5 star property
Falmouth
9.8 out of 10, Exceptional, (178 reviews)
"Quiet and charming B&B. The rooms are great, staff is nice and owners and their dog are great! Walking distance to the Main Street with coffee, restaurants and shops. We stayed a few days with a quick day trip to Martha’s (which we walked to the ferry)"
United States
Jordi
$251 nightly
The price is $287
Nov 1 - Nov 2
Total with taxes and fees
The Palmer House Inn
Front of property - evening/night

5. The Christopher, The Edgartown Collection

The Christopher, The Edgartown Collection
3.0 star property
Edgartown
9.8 out of 10, Exceptional, (288 reviews)
"Friendly and helpful staff - super great location."
United States
Clayton
The Christopher, The Edgartown Collection
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

InnSeason Resorts Surfside

InnSeason Resorts Surfside

10/10 Excellent
"The whole place was very clean. Had a very relaxing time. Views were great too!"
Christine 4-night trip
Posted 1 day ago
InnSeason Resorts Surfside

Find out more about Chilmark

Chilmark B&B information

Number of reviews
879
Accommodation
11 B&B
Lowest Price
$168
Highest Price
$388

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 $168 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.

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