Chilmark Vacation Packages

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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.

Top Chilmark Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Summercamp

Summercamp

3.5 out of 5
Price was CA $1,112, price is now CA $797 per person
CA $797
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Syracuse (SYR) to Vineyard Haven (MVY)
9.2/10 Wonderful! (1,000 reviews)
Staff was knowledgeable and personal. Hotel was convenient and met all of my needs.

Reviewed on Aug. 20, 2025

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Price was CA $1,486, price is now CA $894 per person
CA $894
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Syracuse (SYR) to Vineyard Haven (MVY)
9.2/10 Wonderful! (149 reviews)
It’s a nice boutique hotel but it is in the middle of no where the restaurant across the street is less than desirable. The walk to town is too long on a main street

Reviewed on Aug. 16, 2025

Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
Price was CA $1,506, price is now CA $1,065 per person
CA $1,065
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Syracuse (SYR) to Vineyard Haven (MVY)
9/10 Wonderful! (1,003 reviews)
Beautifully decorated and nice workspace. Staff was not helpful with baggage at check-in. For the price, the toilet paper was cheap and no slippers. It was very nice that they allowed you to use the pool and property after the 11am checkout.

Reviewed on Aug. 9, 2025

Morgan Hotel

Morgan Hotel

2.5 out of 5
Price was CA $1,153, price is now CA $822 per person
CA $822
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Syracuse (SYR) to Vineyard Haven (MVY)
8.4/10 Very Good! (164 reviews)
great location, small but modern

Reviewed on Aug. 19, 2025

The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was CA $1,102, price is now CA $859 per person
CA $859
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip flight included
Syracuse (SYR) to Vineyard Haven (MVY)
8.4/10 Very Good! (8 reviews)
Great spot, very clean and convenient.

Reviewed on Aug. 13, 2025

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 kilometres 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.

Ready to book your vacation to Chilmark?

 

Choose your dates

Chilmark Hotel Deals

Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
The price is CA $200 per night from Sep 1 to Sep 2
CA $200
CA $250 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Conviently located and affordable"

Reviewed on Aug. 17, 2025

Falmouth Inn
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
23 Kelly Street, Martha's Vineyard, Edgartown, MA
The price is CA $568 per night from Sep 15 to Sep 16
CA $568
CA $666 total
Sep 15 - Sep 16
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Wonderful staff!"

Reviewed on Aug. 16, 2025

Faraway Martha's Vineyard
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd, North Falmouth, MA
The price is CA $242 per night from Sep 14 to Sep 15
CA $242
CA $356 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (164 reviews)
"A nice beach front get away. We did not like the extra charge for the second car or the resort fee."

Reviewed on Aug. 16, 2025

Sea Crest Beach Resort
See all 2,302 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

What to do in Chilmark

New Budget Friendly Shared 4 hour African American Heritage Tour

New Budget Friendly Shared 4 hour African American Heritage Tour

CA $179
per adult
New Budget Friendly Shared 4 hour African American Heritage Tour
Massachusetts Highlights: Freedom Trail, Salem & More Tour

Massachusetts Highlights: Freedom Trail, Salem & More Tour

CA $69
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Martha's Vineyard Self-Driving Audio Tour

Martha's Vineyard: Self-Guided Driving Audio Tour

CA $21
per traveller
Martha's Vineyard: Self-Guided Driving Audio Tour
See all activities in Chilmark

Frequently asked questions

How much does a Chilmark vacation package cost?
You'll find cheap prices from CA $797 on Expedia for your Chilmark escape. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Chilmark costs.
What are the cheapest months to go to Chilmark?
January, February and November are great times to look for cheap Chilmark vacation packages. Opting to travel in quieter periods means you can usually find reduced prices on flights and hotels.
How many days is enough for Chilmark?
With a well-organized schedule, you can easily tick off the main Chilmark sights in a handful of days. But if you want to discover hidden gems or go on day trips, think about booking your Chilmark vacation for longer.
Is it worth booking a vacation package to Chilmark?
Chilmark is a good vacation destination with attractions like Lucy Vincent Beach among the many things to keep you busy. Whether you're travelling with the family or planning a trip with friends, a Chilmark vacation promises a good time for everyone.
How to find the best Chilmark package deals?
Use Expedia's filters to find some great Chilmark package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Chilmark package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Chilmark vacation as a package?
You can enjoy significant savings on your next Chilmark escape by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to view some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chilmark?
If you're considering a spontaneous Chilmark adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Chilmark?

  1. Choose when to travel: Check your diary and get packing. Your favourite time of year and the activities available will also help you decide when to vacation in Chilmark.
  2. Plan your budget wisely: In addition to the price of your stay, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside a little extra for unexpected expenses that may arise during your trip to Chilmark.
  3. Decide how long to go for: Now that you know more about Chilmark, you can work out the perfect length of your break. Pull together a rough itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick 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.