Chilmark Trips (flight + hotel)

Photo by Wen C.

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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

Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
60 Beach Road, Vineyard Haven, MA
9/10 Wonderful! (471 reviews)
"Very nice stay"

Reviewed on Jul 30, 2025

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Vineyard Harbor Motel - Private Beach
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 P8,666 per night from Sep 1 to Sep 2
P8,666
P10,791 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,026 reviews)
"Ee"

Reviewed on Aug 1, 2025

Falmouth Inn
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 P10,888 per night from Sep 2 to Sep 3
P10,888
P12,462 total
Sep 2 - Sep 3
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 Jul 13, 2025

Iris Hotel Cape Cod
See all 2,313 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.

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

P7,371
per adult
New Budget Friendly Shared 4 hour African American Heritage Tour
4 hours Hop-on Hop-off Jawsome Jaws Tour

4 hours Hop-on Hop-off Jawsome Jaws Tour

P6,685
per adult
4 hours Hop-on Hop-off Jawsome Jaws Tour
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

P2,834
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
See all activities in Chilmark

Frequently asked questions

How much does a Chilmark vacation package cost?
You can snap up a vacation package to this destination on Expedia. However, how much your vacation 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 vacation packages. Choosing to travel in less busy months means you can usually find lower prices on accommodations and flights.
How many days is enough for Chilmark?
The ideal duration for your Chilmark vacation 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 vacation package to Chilmark?
Chilmark offers everything you need for an unforgettable trip. Begin your Chilmark vacation 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 traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Chilmark vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging stays and flights separately. Better still, you can personalize 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 vacation 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 vacation 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.