Chilmark Vacations

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Photo by Wen C.

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    Save up to ₩234,741 when you book a flight and hotel together*
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Find the Best Chilmark Vacation Packages

Chilmark Hotel Deals

Sea Crest Beach Resort
Sea Crest Beach Resort
3.5 out of 5
350 Quaker Rd, North Falmouth, MA
The price is ₩366,192 per night from Jun 25 to Jun 26
₩366,192
₩497,539 total
Jun 25 - Jun 26
includes taxes & fees
8.2/10 Very Good! (100 reviews)
"Had a great time"

Reviewed on Jun 20, 2025

Sea Crest Beach Resort
Summercamp
Summercamp
3.5 out of 5
70 Lake Avenue, Oak Bluffs, MA
The price is ₩582,925 per night from Jun 30 to Jul 1
₩582,925
₩651,128 total
Jun 30 - Jul 1
includes taxes & fees
9.2/10 Wonderful! (998 reviews)
"I gave an overall rating of 4 because my room was so small, I was totally miserable. This Queen ocean view room, in the older part of the hotel is not worth the rate of over $550 per night. I regret not reserving a king room. I definitely will not make that mistake again. The property itself is an ..."

Reviewed on Jun 22, 2025

Summercamp
Vineyard Harbor Motel - Private Beach
Vineyard Harbor Motel - Private Beach
2.5 out of 5
60 Beach Road, Vineyard Haven, MA
The price is ₩398,386 per night from Jul 9 to Jul 10
₩398,386
₩444,998 total
Jul 9 - Jul 10
includes taxes & fees
8.8/10 Excellent! (419 reviews)
"Friendly and clean"

Reviewed on Jun 22, 2025

Vineyard Harbor Motel - Private Beach
See all 2,289 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?
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.

Discover the most popular places to visit in Chilmark

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