Chilmark Vacations from $585
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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.
Vineyard Harbor Motel - Private Beach
$585
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (773 reviews)
We had a great stay. Place was clean and walkable to the ferry. Staff was nice and helpful, gave us great service and suggestions. The bus stop was close which made easy to go around. Close to grocery store and some shops. Beautiful property
Reviewed on Sep 12, 2026
The Island Inn on Martha's Vineyard
$734
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.4/10 Very Good! (53 reviews)
The worst place we stayed at. The bed was broken and we had to sleep on living room couch…the bathroom doors didn’t look and one bathroom door didn’t close. We complained to front desk in person next day but were not much help and didn’t even bother to change room forget about the upgrade for the inconvenience. It’s nice property but not being maintained by staff and staff not really there to help as they are just there to do minimum and collect their check!
Reviewed on Sep 10, 2026
Harbor View Hotel
$804
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
We had a fantastic week at the Harbor View. Staff were all excellent and helpful!
Loved sitting on the veranda having coffee. Beds and room amenities were great.
The only thing I would have been happier with is if there had been a separate baby pool for the youngest kids. I really enjoyed the pool but once lots of kids and babies started using it I was not interested and felt I was unable to enjoy it.
Reviewed on Sep 12, 2026
Faraway Martha's Vineyard
$675
per person
Dec 6 - Dec 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
It’s a beautiful hotel. Would highly recommend, everyone was lovely and it’s very beautiful to sit outside and to relax
Reviewed on Sep 11, 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.
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.
Chilmark Town Hall
Chilmark Town Hall embodies Martha's Vineyard's understated New England charm while serving as the heart of local governance. Visit during the annual Town Meeting in April to experience authentic island community life.
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.
Chilmark Chocolates
9.4/10 (3 reviews)
This beloved Martha's Vineyard institution crafts exquisite handmade chocolates while employing people with disabilities. Visitors patiently queue for their selection of artisanal treats, often bringing cash.
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.
What to do in Chilmark
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
$50
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
$50
per traveler
Chilmark Hotel Deals
Cozy efficiency apartment/heated pool
Chilmark MA
$452 nightly
$504 total
Sep 14 - Sep 15
Total with taxes and fees
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 refundable
$231 nightly
$264 total
Oct 12 - Oct 13
Total with taxes and fees
7.6/10 Good! (498 reviews)
"I had an amazing time. I love this hotel."
Reviewed on Sep 12, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
$133 nightly
$152 total
Oct 12 - Oct 13
Total with taxes and fees
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 $585 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.
Explore a world of travel with Expedia
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- Flights from New York (LGA) to Vineyard Haven (MVY)
- Flights from New York (LGA) to Nantucket (ACK)
- Flights from Philadelphia (PHL) to Vineyard Haven (MVY)
- Flights from San Francisco (SFO) to Vineyard Haven (MVY)
- Flights from Atlanta (ATL) to Vineyard Haven (MVY)
- Flights from Newark Liberty Intl. Airport (EWR) to Vineyard Haven (MVY)
- Flights from Hartford (BDL) to Vineyard Haven (MVY)
- Flights from White Plains (HPN) to Vineyard Haven (MVY)
- Flights from Baltimore (BWI) to Vineyard Haven (MVY)
- Flights from Boston (BOS) to Vineyard Haven (MVY)
- Flights from New York (JFK) to Vineyard Haven (MVY)
- Flights to Nantucket Island
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- Flights from Martha's Vineyard
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- Flights from Chicago (ORD) to Vineyard Haven (MVY)
- Flights from Washington (DCA) to Vineyard Haven (MVY)
- Flights to Cape Cod
- Flights from Los Angeles (LAX) to Vineyard Haven (MVY)
- Visit Martha's Vineyard
- Fulling Mill Brook Preserve
- Tisbury Town Hall & Katharine Cornell Memorial Theater
- Martha's Vineyard Film Center
- Visit Hyannis Port
- Inkwell Beach
- Katama Beach
- Tisbury Town Beach
- Felix Neck Wildlife Sanctuary
- Visit Falmouth
- Nantucket Vacations
- Nobska Lighthouse
- Island Cove Adventures
- Oak Bluffs Vacations
- Gay Head Lighthouse
- Martha's Vineyard Chamber of Commerce
- Dr Daniel Fisher House
- Visit Chilmark
- Visit Menemsha
- Surf Drive Beach
- Aquinnah Cliffs
- Chilmark Chocolates
- Long Point Beach
- Lucy Vincent Beach
- Menemsha Beach
- Martha's Vineyard Museum
- All inclusive Vacation Packages Martha's Vineyard
- Long Point Wildlife Refuge
- Joseph Sylvia State Beach
- Circuit Avenue
- Gus Ben David's World of Reptiles and Birds Park
- Farm Neck Golf Club
- Vineyard Haven Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
