Chilmark Holidays

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Your Chilmark Holiday

With a reputation for its unspoiled nature and spectacular views, Chilmark is a perfect getaway destination. Book one of our Chilmark holiday packages and enjoy all that this fascinating city has to offer. If a sightseeing tour is on the agenda during your trip to Chilmark, look around major attractions like Aquinnah Cliffs, Gay Head Lighthouse and Menemsha Beach. No matter your travel plans or the size of your budget, putting together the ultimate tailored Chilmark holiday is a cinch with Expedia.

Chilmark Beach Holiday

Whether you're travelling solo or with the whole gang, it'll be easy to find rest and relaxation on your Chilmark holiday. Search around for shiny rocks and shells or simply sit and watch the sunset. Whatever you choose to do, your trip to Chilmark will certainly be memorable. Lucy Vincent Beach, located 1 mile from the town centre, is perfect for those after convenience. Many visitors also lock in Chilmark holiday packages closer to Menemsha Beach, another great nearby option.

Chilmark Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Martha's Vineyard Airport (MVY)
Population
860
Max Temp Winter
4ºC
Max Temp Summer
21ºC
Top Sights
Marthas Vineyard Museum, Lamberts Cove Beach and South Beach

Top hotels in Chilmark

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Chilmark, MA
9.8/10 Exceptional! (49 reviews)
Excellent Location in Chilmark. Great accommodation.
"We spent two weeks on Cape Cod and Martha’s Vineyard this summer, and the few days we spent here were the best. The communication with the host reserving the property, getting great advice regarding scheduling ferries, and information on Lucy Vincent Beach was incredible! We were able to go to Lucy ..."

Reviewed on 5 Jul 2025

Get rates
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is £170 per night from 4 Aug to 5 Aug
£170
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (54 reviews)
Did the trick
"Clean room, building and rooms are a bit dated. Would return, fairly priced."

Reviewed on 13 Jul 2025

Iris Hotel Cape Cod
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road, Vineyard Haven, MA
The price is £255 per night from 31 Aug to 1 Sept
£255
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (471 reviews)
"Very nice stay"

Reviewed on 30 Jul 2025

Vineyard Harbor Motel - Private Beach
See all 2,316 properties in Chilmark
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Lucy Vincent Beach

If a restful holiday is part of your travel plans, Lucy Vincent Beach might be the perfect place to visit during your trip to Chilmark. Take in the festivals and sunsets in the area.

Lucy Vincent Beach

What to do in Chilmark

Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

£11
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

£37
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
All Island Bus Tour

All Island Bus Tour

£56
per adult
80% of travellers recommend
All Island Bus Tour
See all activities in Chilmark

Frequently asked questions

Why should I book my Chilmark holiday with Expedia?
Expedia has you covered for every detail of your Chilmark getaway. You'll always get the best deal possible, but when you bundle your hotel, flights and/or hire car into a holiday package, you'll score even bigger savings. Want to truly make the most of your escape? Add some exciting activities and tours to your package. We offer flexible cancellation policies on most bookings, so you won't need to worry if your travel plans change. Visit our Customer Service Portal link to discover more.
When is the best time of year to holiday in Chilmark?
Into sightseeing but don't like queuing up for attractions? Organise your Chilmark getaway for November, December and January. Typically, it's a lot quieter than in June, July and August. With average daytime temperatures of 1ºC, January is the coolest period in Chilmark. The warmest time of year is August, when you can experience averages of 22ºC throughout the day. Whatever the temperature, you'll find plenty to keep you occupied here.
What is the top hotel for my holiday in Chilmark?
Boston Park Plaza is a perfect base for an unforgettable holiday in Chilmark, offering all the comforts and amenities you need and more.
How do I get a cheap holiday to Chilmark?
One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, hire cars, flights and activities — we've got them all. Pick and choose a combination that suits your style and see your savings grow. Of course, holidays are never one-size-fits-all. That's why we offer more than 400 air carriers and 321,000 hotel options globally, so you can customise your Chilmark holiday your way. Learn more about how you can save money on your next holiday when you combine your flight and hotel bookings with Expedia.
What should I do on my Chilmark holiday?
There are lots of things to do and see while enjoying a holiday in Chilmark. Aquinnah Cliffs, Lamberts Cove Beach, Gay Head Lighthouse and Marthas Vineyard Preservation Trust Historic Buildings are among this city's major attractions.
What is the best area to stay in when on holiday in Chilmark?
If you plan to visit Aquinnah Cliffs, maximise your time sightseeing and book a stay nearby. It's one of the most popular attractions in Chilmark.
Do I need a visa for my Chilmark holiday?
Check the most up-to-date information on official government websites. Your nationality and whether you're travelling for leisure, study or business will determine if you'll need a visa for Chilmark. Make yourself familiar with the application process, including any required documentation, turnaround times and fees. Finalise your application well in advance to allow enough time for processing. Some visas can take many weeks or even months to obtain, depending on the country.
What should I wear on my Chilmark holiday?
Do a little research into the sorts of things people in Chilmark wear, and maybe even look up fashion pages on social media for inspiration. Whatever your look, try to create a versatile travel wardrobe filled with pieces that work for your destination and showcase your unique sense of style. Check the local weather forecast so you can pack accordingly. The warmest month in Chilmark is August, with average daytime temperatures of 22ºC. If you're visiting in the coolest month of January, the mercury averages 1ºC during the day.
What does an Expedia Chilmark holiday include?
Expedia has all you need to plan your Chilmark getaway, but what your package looks like is your choice. Choose from any combination of flights, hotels and hire cars. Searching for some activities to keep you on the go? Once you've made your booking, you can add them too. No matter your budget or style, there's a holiday package to meet your needs. Explore a huge range of property types and pick one that suits your group size. The most popular rentals here are private holiday homes and cottages. With Expedia, you can easily tailor-make your Chilmark retreat however you like.
Does Expedia offer Book Now, Pay Later Chilmark holidays?
Yes, we do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply choose the payment plan that suits best during the checkout process and take the stress out of budgeting for your trip. Make sure you bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Browse our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all types of budgets, so you can have that well-deserved holiday sooner.
  • No-deposit holidays: If no upfront fee for your getaway makes clicking that "book now" button easier, opt for a no-deposit holiday plan from Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Chilmark Expedia holiday?
Yes, definitely. Expedia has more than 400 partner airlines to choose from all over the world. With so much choice, finding the ideal carrier to fly you to Chilmark won't be hard.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.