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

Cozy efficiency apartment/heated pool

Cozy efficiency apartment/heated pool

Chilmark MA
9.6/10 Exceptional! (22 reviews)
"Great location and pass to the most beautiful beach. Pool was lovely to have as well."

Reviewed on 1 Jul 2026

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Cozy efficiency apartment/heated pool
Private Hilltop Chilmark Estate with private tennis court, gym and hot tub

Private Hilltop Chilmark Estate with private tennis court, gym and hot tub

Chilmark MA
2/10 (1 review)
Vacationing while black
"The owner agreed to let me have a few guests onsite but then became belligerent, rude, and nasty when his neighbors alleged I had an event 3 days after said date. I was told i was not welcomed in Chilmark and thrown off the property. VRBO sided with the property owner. Seems to be the practice when ..."

Reviewed on 23 Aug 2022

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Private Hilltop Chilmark Estate with private tennis court, gym and hot tub
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is €218 per night from 19 Jul to 20 Jul
€218
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (285 reviews)
"Great and friendly lady that maintained our room. Front desk was difficult to reach - had to call over and over and no one would respond - the front desk girl was not that friendly- the tub would clog- bed was super comfortable - it was just ok for me."

Reviewed on 11 Jul 2026

Iris Hotel Cape Cod
See all 2,280 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.

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.
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What to do in Chilmark

Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

€13
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

€43
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

€43
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
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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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.

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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.