Chilmark Vacations from $1,558
Book a Hotel + Flight or Car together to unlock savings
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.
Vineyard Harbor Motel - Private Beach
$1,620
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Vineyard Haven (MVY)
9/10 Wonderful! (812 reviews)
Loved the motel. Next time I’ll call them straight away. Expedia took me for an extra $60.00. I won’t be using Expedia again.
Reviewed on Oct 25, 2026
Stay near popular Chilmark attractions
Menemsha Beach
This serene beach offers gentle surf and a front-row seat to Martha's Vineyard's most spectacular sunsets. Purchase fresh seafood from nearby markets to create a memorable oceanside dining experience.
The Yard
This renowned contemporary dance center on Martha's Vineyard showcases innovative choreography in an intimate 100-seat theater. Arrive early to enjoy the charming Shell Garden with pre-show drinks under twinkling lights.
Middle Road Sanctuary
Walk through glacial history on trails winding past massive boulders and steep ridges. The sanctuary offers serene views of three ponds, perfect for nature photography and bird watching.
Fulling Mill Brook Preserve
This tranquil 66-acre preserve offers diverse habitats from dense woodlands to wetlands along a scenic brook. Explore the loop trail to spot nesting songbirds like yellow warblers while crossing charming footbridges.
Stonewall Beach
Stonewall Beach offers a secluded rocky shoreline with mesmerizing wave patterns. Bring sturdy footwear to explore this tranquil Chilmark hideaway with minimal crowds but maximum natural beauty.
Squibnocket Beach
Why not spend a lazy afternoon at Squibnocket Beach during your trip to Chilmark? Stroll along the beaches or experience the area's festivals.
Wades Field
You can take time to visit Wades Field during your travels to Chilmark. Amble around the area's beaches or experience its festivals.
Waskosim's Rock Reservation
You can take time to visit Waskosim's Rock Reservation during your travels to Chilmark. Stroll along the area's waterfront, or simply savor its wineries.
What to do in Chilmark
Massachusetts Self-Guided GPS Audio Tour Bundle (11 Tours)
$50
per adult
Edgartown Martha’s Vineyard Self-Guided (GPS) Audio Walking Tour
$10
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
$50
per traveler
Chilmark Hotel Deals
Cozy efficiency apartment/heated pool
Chilmark MA
9.6/10 Exceptional! (26 reviews)
"Beautiful property with an amazing pool. Great place to stay!"
Reviewed on Aug 30, 2026
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
$169 nightly
$193 total
Nov 8 - Nov 9
Total with taxes and fees
7.6/10 Good! (540 reviews)
"Nice room. Didnt have a balcony and our view was of the other building. Spacious rooms and clean !"
Reviewed on Oct 25, 2026
Inn on the Square
40 North Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
$152 nightly
$174 total
Nov 24 - Nov 25
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
"We enjoyed having a glass of wine by the fire pit in the courtyard area, and the adjoining restaurant for breakfast. Our primary interest was proximity to the Shining Sea Bikeway which was just a block away. Easy stroll to the downtown area with lots of shops and restaurants. We did not use the indoor ..."
Reviewed on Oct 24, 2026
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.
Find the Best Chilmark Vacation Packages
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.
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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Frequently asked questions
How much does a Chilmark vacation package cost?
You can snap up a vacation package to this destination from $1,558 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?
- Choose your travel dates: What you want to do in Chilmark and your preferred season will help you decide when to travel.
- 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.
- 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.
- 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.
- Combine your airfare and accommodations: After you've settled on your dates and duration, book the right Chilmark vacation package for you.
- 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.