Chilmark Trips (flight + hotel)

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Chilmark Beach Vacation

Whether you're traveling solo or with the whole gang, it'll be easy to find rest and relaxation on your Chilmark vacation. 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 2 kilometers from the town center, is perfect for those after convenience. Many visitors also lock in Chilmark vacation packages closer to Menemsha Beach, another great nearby option.

Top hotels in Chilmark

Sea Crest Beach Hotel
Sea Crest Beach Hotel
3.5 out of 5
350 Quaker Rd, North Falmouth, MA
The price is P7,317 per night from 5 May to 6 May
P7,317
per night
5 May - 6 May
7.8/10 Good! (1,003 reviews)
"Loved you front desk stafff"

Reviewed on Apr 27, 2024

Sea Crest Beach Hotel
Harbor View Hotel
Harbor View Hotel
5 out of 5
131 N Water Street Marthas Vineyard, Edgartown, MA
The price is P22,821 per night from 2 May to 3 May
P22,821
per night
2 May - 3 May
8.8/10 Excellent! (941 reviews)
Great location; beautiful views. Peaceful retreat
"We had a beautiful room in the old house with amazing views over the ocean. Very special."

Reviewed on Apr 19, 2024

Harbor View Hotel
Summercamp
Summercamp
3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is P11,381 per night from 6 May to 7 May
P11,381
per night
6 May - 7 May
9/10 Wonderful! (575 reviews)
Very accommodating staff
"The front desk completely accommodated our desire to be in the main building vs the annex. They provided us with a king room with a view on the 3rd floor despite not being fully opened on the upper floors. Everyone was super hospitable & friendly. We will definitely return for another stay."

Reviewed on Apr 21, 2024

Summercamp
See all 2,207 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.

Frequently asked questions

How much does a Chilmark vacation package cost?
Our Chilmark vacation packages, which start from as low as , are an easy way to save precious money. All you have to do is choose your preferred hotels, flights and more to create a customized escape.
How do I get a cheap travel package to Chilmark?
Creating your own Chilmark vacation package with Expedia is one of the best ways to save. We have over 550 partner airlines and 1,000,000 hotels globally. With such a broad range to choose from, you’ll have no hassles creating your dream adventure.
Where should I stay in Chilmark?
With lots to explore in Chilmark, we suggest you lock in a hotel close to its attractions. Lucy Vincent Beach, Menemsha Beach and The Yard are some popular ones to put on your to-do list.
What are the top hotels in Chilmark?
Make a reservation at Menemsha Inn & Cottages. It’s one of the area’s most popular hotels. Another highly rated option in Chilmark is Cozy Efficiency Apartment/heated Pool.
How far in advance should I book my Chilmark vacation?
Reward yourself with the widest variety at the cheapest prices by booking your trip to Chilmark nice and early. Air carriers tend to release tickets around 12 months prior to departure, so secure your spot as soon as you can. Having said that, Expedia is committed to giving you the best bargains around, so it’s never a bad time to book your dream vacation!
What does an Expedia Chilmark travel package include?
Expedia has everything you need to lock in Chilmark trip, but what goes into your package is your choice. Select from a combination of flights, rental cars and hotels. After some tours or activities to keep you entertained? Once you’ve made your booking, you can add them on too. No matter your budget or style, there’s a package deal to meet your needs.
What should I know before booking a Chilmark travel package?
Booking all the parts of your trip together is an excellent way to save. Bundle your car rentals, flights and hotels into a handy little package. But hotels aren’t your only option. Expedia has all types of properties, including vacation rentals like oceanfront condos and spacious residences. You’ve got choices galore!
Can I choose my airline with a Chilmark Expedia vacation package?
Yes, and with more than 550 airlines to choose from around the world, you have plenty of choice. Take a look at the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Chilmark vacation package?
If your vacation plans in Chilmark have changed, it’s a relief to know that it is possible to amend or cancel your booking. If you made your booking in the last 24 hours, you may be able to receive a refund. If your booking is older than that, your airline, hotel or car rental company may impose a cancellation fee. To learn more, check our Customer Service Portal.

Popular places to visit

Image for Menemsha Beach

Menemsha Beach

Why not spend a carefree afternoon at Menemsha Beach during your travels in Chilmark? Take in the festivals and sunsets in the area.

Menemsha Beach
Image for Lucy Vincent Beach

Lucy Vincent Beach

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

Lucy Vincent Beach
Image for Chilmark Chocolates

Chilmark Chocolates

Enjoy an outing to Chilmark Chocolates during your stay in Chilmark. While in this walkable area, you can savor the wineries.

Chilmark Chocolates

What to do in Chilmark

Image for Martha’s Vineyard Self-Guided (APP/GPS) Audio Walking Tour

Martha’s Vineyard Self-Guided (APP/GPS) Audio Walking Tour

P429
Per adult
Martha’s Vineyard Self-Guided (APP/GPS) Audio Walking Tour
Image for Marthas Vineyard Tour: Self-Guided Drive

Marthas Vineyard Tour: Self-Guided Drive

P746
Per adult
86% of travellers recommend
Marthas Vineyard Tour: Self-Guided Drive
Image for Martha's Vinyard Driving & Walking GPS-Guided Audio Tour

Martha's Vinyard Driving & Walking GPS-Guided Audio Tour

P829
Per adult
Martha's Vinyard Driving & Walking GPS-Guided Audio Tour
See all activities in Chilmark

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.