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.
Faraway Martha's Vineyard
CA $4,201
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,000 reviews)
We LOVED our stay at Faraway - the pool was amazing, staff was super helpful. They had a very convenient messaging system for requests. The staff recommended the Pelican Club for dinner, which is basically right on-site, but we tried to get in multiple times and there was always a wait! The food at their snack bar was really good for lunch. The location was incredible - it was our first time in Martha's Vineyard and we feel we got so spoiled!!
Reviewed on Aug 11, 2026
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?
Chilmark Hotel Deals
Cozy efficiency apartment/heated pool
Chilmark MA
CA $488
CA $740 total
Sep 10 - Sep 11
includes taxes & fees
9.6/10 Exceptional! (22 reviews)
"Great location and pass to the most beautiful beach. Pool was lovely to have as well."
Reviewed on Jul 1, 2026
Iris Hotel Cape Cod
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
CA $190
CA $217 total
Sep 8 - Sep 9
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 Aug 9, 2026
Sea Crest Beach Resort
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
CA $421
CA $561 total
Sep 7 - Sep 8
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 Aug 10, 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
Why not spend a carefree afternoon at Menemsha Beach during your travels in Chilmark? Take in the festivals and sunsets in the area.
Stonewall Beach
Why not spend a lazy afternoon at Stonewall Beach during your trip to Chilmark? Stroll along the beaches or discover the area's sunsets.
Chilmark Town Hall
After visiting Chilmark Town Hall, make a plan to see the other sights and activities in Chilmark. Wander the beaches or discover the area's sunsets.
The Yard
Walk around the campus at The Yard during your stay in Chilmark. Stroll along the area's waterfront, or simply savor its wineries.
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)
Enjoy an outing to Chilmark Chocolates during your stay in Chilmark. While in this walkable area, you can savor the wineries.
Chilmark Public Library
After visiting Chilmark Public Library, make a plan to see the other sights and activities in Chilmark. Amble around the area's beaches or experience its festivals.
Middle Road Sanctuary
You can take time to visit Middle Road Sanctuary during your travels to Chilmark. Take in the festivals and sunsets in the area.
What to do in Chilmark
Martha's Vineyard: Self-Guided Driving Audio Tour
CA $21
per traveller
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
CA $70
per adult
Massachusetts: Smartphone-Based Audio Tour Bundle
CA $71
per traveller
Frequently asked questions
How much does a Chilmark vacation package cost?
You'll find cheap prices from CA $2,698 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?
- 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.
- 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.
- 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.
- 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.
