Chilmark Packages (Flight + Hotel)

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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 2 kilometres 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.

Top hotels in Chilmark

Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is ฿4,852 per night from 1 Sept to 2 Sept
฿4,852
฿6,042 total
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (1,011 reviews)
"I like how centrally-located the hotel was to the Falmouth Road Race and other important areas in town. Also LOVED the onsite restaurant."

Reviewed on 20 Aug 2025

Falmouth Inn
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
23 Kelly Street, Martha's Vineyard, Edgartown, MA
8.8/10 Excellent! (1,001 reviews)
"Wonderful staff!"

Reviewed on 16 Aug 2025

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Faraway Martha's Vineyard
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd, North Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is ฿5,675 per night from 14 Sept to 15 Sept
฿5,675
฿8,359 total
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (168 reviews)
"Great for families as everything is close, inside/outside pool and beach. Beach water was clean, small waves, a little rocky area as you walk in but after that it’s soft sand. Pool bathrooms were full of flies, dead and alive. Room was okay, killed 2 flies and 1 spider, but daily cleanings. Fridge/freezer, ..."

Reviewed on 18 Aug 2025

Sea Crest Beach Resort
See all 2,268 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.

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

New Budget Friendly Shared 4 hour African American Heritage Tour

New Budget Friendly Shared 4 hour African American Heritage Tour

฿4,258
per adult
New Budget Friendly Shared 4 hour African American Heritage Tour
Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

฿491
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
Martha’s Vineyard Self-Guided

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

฿319
per adult
Martha’s Vineyard Self-Guided (APP/GPS) Audio Walking Tour
See all activities in Chilmark

Frequently asked questions

How much does a Chilmark holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday to Chilmark costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chilmark?
January, February and November are great times to look for cheap Chilmark holiday packages. Choosing to travel in less busy months means you can usually find lower prices on accommodation and flights.
How many days is enough for Chilmark?
The ideal duration for your Chilmark holiday depends on what you'd like to do and see. Generally, a few days to a week will give you time to check out all the main sights and discover some hidden gems along the way.
Is it worth booking a holiday package to Chilmark?
Chilmark offers everything you need for an unforgettable trip. Begin your Chilmark holiday on a high note by visiting popular attractions like Lucy Vincent Beach.
How to find the best Chilmark package deals?
Landing a cheap Chilmark package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Chilmark package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Chilmark holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging stays and flights separately. Better still, you can personalise your Chilmark getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a holiday package to Chilmark?
If you've got your Chilmark travel dates finalized, book as early as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Chilmark?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Chilmark.
  2. Set a budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to Chilmark. Then, pick a hotel that suits your budget, whether that's an affordable stay or a deluxe getaway.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Chilmark. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Chilmark holiday package that brings all your bookings together.

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