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

Sea Crest Beach Resort
Sea Crest Beach Resort
3.5 out of 5
350 Quaker Rd, North Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is S$284 per night from 16 Apr to 17 Apr
S$284
includes taxes & fees
16 Apr - 17 Apr
8.4/10 Very Good! (54 reviews)
"Every staff member we encountered was very nice, professional, and accommodating. Pool was clean. Stairs and hallway leading to the rooms needs more attention with cleaning. The room itself was clean and comfortable. The bathroom wall needed some spot cleaning. Overall we were happy and would stay ..."

Reviewed on 25 Mar,2025

Sea Crest Beach Resort
Admiralty Inn & Suites - a Red Collection Hotel
Admiralty Inn & Suites - a Red Collection Hotel
3 out of 5
51 Teaticket Highway, East Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is S$174 per night from 7 Apr to 8 Apr
S$174
includes taxes & fees
7 Apr - 8 Apr
8.6/10 Excellent! (174 reviews)
"Was decent"

Reviewed on 23 Mar,2025

Admiralty Inn & Suites - a Red Collection Hotel
Falmouth Tides
Falmouth Tides
2.5 out of 5
267 Clinton Ave, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is S$273 per night from 2 Apr to 3 Apr
S$273
includes taxes & fees
2 Apr - 3 Apr
9.2/10 Wonderful! (537 reviews)
Clean, comfortable room by the Ocean!
"Loved the location and the value love the comfort in the room, and the record player was especially fun!"

Reviewed on 29 Mar,2025

Falmouth Tides
See all 2,216 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.

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.

What to do in Chilmark

4 hours Hop-on Hop-off Jawsome Jaws Tour

4 hours Hop-on Hop-off Jawsome Jaws Tour

S$160
per adult
4 hours Hop-on Hop-off Jawsome Jaws Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts Self-Guided Driving and Walking Tours Bundle

S$67
per adult
Massachusetts Self-Guided Driving and Walking Tours Bundle
Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

S$18
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
See all activities in Chilmark

* 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.