Chilmark Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 2 kilometers 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 Hotel Deals
Cozy efficiency apartment/heated pool
Chilmark MA
￥49,925
￥78,807 total
Sep 9 - Sep 10
includes taxes & 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 refundableReserve now, pay when you stay
￥43,119
￥58,293 total
Oct 4 - Oct 5
includes taxes & fees
7.6/10 Good! (481 reviews)
"It was a magical stay with my loving life Partner Diane,great beach, great views of the shoreline,great food at the lantern.Very courteous and pleasant staff on all fedepartments,from the start till the end of our vacation.. Loved it and can't to return Greg Freitas and Diane Talbot Wood.."
Reviewed on Sep 5, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
￥25,714
￥29,430 total
Oct 4 - Oct 5
includes taxes & fees
8.2/10 Very Good! (374 reviews)
"The bedding in this property has been significantly upscaled. The beds, linens and pillows are all absolutely comfortable. The rooms were clean and very large. The breakfast that came with the room was far beyond any continental I’ve ever had. Everything was fresh. There were high-end pastries, and ..."
Reviewed on Sep 5, 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.
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.
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.
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.
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
￥7,910
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
￥8,003
per traveler
Martha's Vineyard Private 4 hour Tour for groups up to 6 people
￥112,063
per traveler
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?
- 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.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
