A dock with boats, a small wooden structure, and a forested shoreline.

Chilmark Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
  • Dec 27 - Dec 30

    The Franklin Hotel Martha's Vineyard + Flight

    Edgartown
    3 nights
    2.0 star property
    9.0/10 - Wonderful (222 reviews)
    Roundtrip • Toronto (YYZ) - Vineyard Haven (MVY)
    YYZ - HYA • 2 stops HYA - YYZ • 2 stops
    CA $2,084
    CA $2,044
    per traveller
    found 1 day ago
    The Franklin Hotel Martha's Vineyard
  • Dec 27 - Dec 30

    Vineyard Harbor Motel - Private Beach + Flight

    Vineyard Haven
    3 nights
    2.5 star property
    9.0/10 - Wonderful (841 reviews)
    Roundtrip • Toronto (YYZ) - Vineyard Haven (MVY)
    YYZ - HYA • 2 stops HYA - YYZ • 2 stops
    CA $2,207
    CA $2,104
    per traveller
    found 1 day ago
    Vineyard Harbor Motel - Private Beach
  • Dec 27 - Dec 30

    Harbor View Hotel + Flight

    Edgartown
    3 nights
    5.0 star property
    8.8/10 - Excellent (1,000 reviews)
    "Loved the heated saltwater pool. Was disappointed there was not comfortable sitting in the room, esp on a rainy day or not feeling well, and watching a movie. Was surprised no elevator and we were on the third floor. The “grab and go” breakfast option was no more than a few pastries. That was disappointing. For early departure to catch ferry at 0530, no coffee was available."
    Reviewed October 22, 2026
    Roundtrip • Toronto (YYZ) - Vineyard Haven (MVY)
    YYZ - HYA • 2 stops HYA - YYZ • 2 stops
    CA $2,410
    CA $2,335
    per traveller
    found 1 day ago
    Harbor View Hotel

Discover the most popular places to visit in Chilmark

What to do in Chilmark

Chilmark Hotel Deals

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 vacation package cost?

You'll find cheap prices from CA $2,044 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.