Chilmark Holidays
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Chilmark Beach Holiday
Whether you're travelling solo or with the whole gang, it'll be easy to find rest and relaxation on your Chilmark holiday. 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 kilometres from the town centre, is perfect for those after convenience. Many visitors also lock in Chilmark holiday packages closer to Menemsha Beach, another great nearby option.
Top hotels in Chilmark
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
S$199
7 Sept - 8 Sept
includes taxes & fees
8.4/10 Very good! (330 reviews)
"Check in was easy and staff was friendly. Rooms were okay, the floors weren’t cleaned well but the bed was comfy."
Reviewed on 9 Aug, 2026
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundable
S$516
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (425 reviews)
"The property has a charming character, but it could use some updates and repairs to make it perfect. On the bright side, the beach nearby is wonderful, and all the amenities are fantastic. It’s a lovely place with lots of potential!"
Reviewed on 10 Aug, 2026
Falmouth Inn
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
S$221
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (1,035 reviews)
"The rooms were very clean but the pool was nasty, almost like swamp water. It wasn't clean, the area was hot and musty smelling. The water was so dirty, you couldn't see the bottom of the pool and it appeared to be oil floating on top of the water. You would have thought it was an outdoor pool but ..."
Reviewed on 11 Aug, 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 mesmerising wave patterns. Bring sturdy footwear to explore this tranquil Chilmark hideaway with minimal crowds but maximum natural beauty.
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.
The Yard
This renowned contemporary dance centre on Martha's Vineyard showcases innovative choreography in an intimate 100-seat theatre. 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 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.
Chilmark Public Library
This charming community hub houses an impressive collection of books and hosts enriching cultural events. Browse local literature or attend a seasonal art exhibition in this welcoming Martha's Vineyard sanctuary.
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.
What to do in Chilmark
Martha's Vineyard: Self-Guided Driving Audio Tour
S$19
per traveller
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
S$65
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
S$64
per traveller
Frequently asked questions
How much does a Chilmark holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday 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 holiday packages. Choosing to travel in less busy months means you can usually find lower prices on accommodation and flights.
How many days is enough for Chilmark?
The ideal duration for your Chilmark holiday 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 holiday package to Chilmark?
Chilmark offers everything you need for an unforgettable trip. Begin your Chilmark holiday 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Chilmark holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging stays and flights separately. Better still, you can personalise 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 holiday 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
