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Your Chilmark Vacation

With a reputation for its unspoiled nature and spectacular views, Chilmark is a perfect getaway destination. Book one of our Chilmark vacation 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 vacation is a cinch with Expedia.

The Latest Chilmark Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Attleboro House
The Edgartown Inn, The Edgartown Collection
The Christopher, The Edgartown Collection
Morgan Hotel
The Coco, The Edgartown Collection

Find the Best Chilmark Vacation Packages

Chilmark Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Martha's Vineyard Airport (MVY)
Population
860
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Marthas Vineyard Museum, Lamberts Cove Beach and South Beach

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Chilmark Hotel Deals

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Chilmark
6/10 (2 reviews)
Wonderful stay in Chilmark
"We had such a lovely time staying at this house. It was absolutely immaculate inside and appointed with everything we could need and more. The house is light and airy inside, which helped when we had a few days of rain. The location is secluded in the woods (be careful, we did find ticks on us) but ..."

Reviewed on Aug 9, 2024

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
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 $193 per night from May 11 to May 12
$193
includes taxes & fees
$169 per night
May 11 - May 12
8/10 Very Good! (70 reviews)
Beautiful location, beat up room
"Beautiful resort overall. Our room was beat up though. The door was cracked (like 6 inches) at the door lock. Looks like someone tried to break in or out and the door hadn’t been replaced. Door still locked but gave me the creeps a little. Also, mislead by “ocean front.” This does not mean your room ..."

Reviewed on Apr 28, 2025

Sea Crest Beach Resort
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 $140 per night from May 8 to May 9
$140
includes taxes & fees
$122 per night
May 8 - May 9
7.6/10 Good! (10 reviews)
"I understand the property is undergoing maintenance and upgrades. The hotel is fine, though we found it to smell a bit musty and be showing some age. Rooms were acceptable and kids enjoyed the pool. Convenient location."

Reviewed on Apr 25, 2025

Iris Hotel Cape Cod
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 from $472 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?
If you’d like to snag a cheap Chilmark vacation package, consider traveling in November, December and January. You’ll usually find lower rates on flights and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Chilmark?
The ideal duration of your Chilmark vacation depends on what you’d like to do. Usually, a handful of days to a week will give you time to visit all the top sights and discover some hidden spots along the way.
Is it worth booking a vacation package to Chilmark?
Chilmark offers everything you need for a wonderful getaway. Get your Chilmark vacation off to a flying start by exploring popular attractions like Menemsha 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. Choose your travel dates: What you want to do in Chilmark and your preferred season will help you decide when to travel.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Chilmark.
  3. Use Expedia’s trip planning tool to discover Chilmark: Research every aspect of your trip to Chilmark with this handy planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how many days away: Start by listing all the activities and sights you want to get to in Chilmark. Then, estimate how long you’ll need for each, along with any travel time.
  5. Combine your airfare and accommodations: After you’ve settled on your dates and duration, book the right Chilmark vacation package for you.
  6. Add on excursions and experiences: Have a look at our travel guide to find some fun things to do in Chilmark. Book tickets or make reservations in advance to save time and avoid the hassle of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Chilmark vacation packages?
Your Chilmark getaway is meant to be an escape from your daily routine, not a reason for money worries. So to give you more flexibility, we’ve partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren’t any hidden or late payment fees to worry about.

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