Chilmark Vacations from $1,362

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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.
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
per person
Nov 7 - Nov 11
found 4 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Vineyard Haven (MVY)
9/10 Wonderful! (1,003 reviews)
Beautifully decorated and nice workspace. Staff was not helpful with baggage at check-in. For the price, the toilet paper was cheap and no slippers. It was very nice that they allowed you to use the pool and property after the 11am checkout.

Reviewed on Aug 9, 2025

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
9.2/10 Wonderful! (149 reviews)
We thoroughly enjoyed or stay here.

Reviewed on Aug 10, 2025

Summercamp

Summercamp

3.5 out of 5
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
9.2/10 Wonderful! (1,000 reviews)
The guests were there to have a good time; that made folks friendly. That, in turn, made the experience nice.

Reviewed on Aug 11, 2025

Morgan Hotel

Morgan Hotel

2.5 out of 5
per person
Sep 24 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
8.4/10 Very Good! (164 reviews)
AC is a bit noisy in this tiny room, but location is great.

Reviewed on Aug 11, 2025

The Coco, The Edgartown Collection

The Coco, The Edgartown Collection

3 out of 5
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Vineyard Haven (MVY)
9.8/10 Exceptional! (53 reviews)
Staff was very accomodating..Breakfast was excellent..room was beautiful. Close to lots of restaurants and shops..i loved it all.

Reviewed on Jul 21, 2025

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Discover the most popular places to visit in Chilmark

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

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

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

New Budget Friendly Shared 4 hour African American Heritage Tour

New Budget Friendly Shared 4 hour African American Heritage Tour

$130
per adult
New Budget Friendly Shared 4 hour African American Heritage Tour
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

$50
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Chilmark

Chilmark Hotel Deals

Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $178 total per night from Sep 15 to Sep 16
$178 total
Sep 15 - Sep 16
Total includes taxes and fees
7.8/10 Good! (1,011 reviews)
"Restaurant right next door. Convenient breakfast. Easy check in and out. Good customer service- quick resolve of missing towels. Bathroom showerhead height too short- had to bend to wash hair. Overall good experience."

Reviewed on Aug 12, 2025

Falmouth Inn
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
$239 nightly
The price is $273 total per night from Sep 3 to Sep 4
$273 total
Sep 3 - Sep 4
Total includes taxes and fees
7.8/10 Good! (159 reviews)
"Our room constantly smelled like someone just used the bathroom other than that pretty good stay"

Reviewed on Aug 9, 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
$164 nightly
The price is $188 total per night from Sep 15 to Sep 16
$188 total
Sep 15 - Sep 16
Total includes taxes and fees
7.8/10 Good! (63 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 2,297 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.

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 1 mile (2 km) 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.

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Frequently asked questions

How much does a Chilmark vacation package cost?
You can snap up a vacation package to this destination from $1,362 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.