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
CA $1,601
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.4/10 Exceptional! (1,000 reviews)
Small room, no coffee in room. Parking fine, additional cost. Had showers available when room no longer was which was good, doors have traditional keys and didn’t seem very secure. Overall good vibe and fantastic staff just not quite at value for the cost of almost $900 a night
Reviewed on Aug 6, 2026
Morgan Hotel
CA $1,730
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.6/10 Excellent! (243 reviews)
The first room we were in was right next to the street and lobby and was quite loud. They were very accommodating and moved us upstairs to a quiet room. Overall a great hotel with great service.
Reviewed on Aug 4, 2026
Faraway Martha's Vineyard
CA $3,168
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9/10 Wonderful! (1,004 reviews)
We came here on our anniversary and could not have picked a better place. The boutique-yet-full-service hotel is elegant and beautiful, with great taste everywhere and amazing ocean views. The heated (perfect temperature) pool and jacuzzi were a perfect spot to take a break at any time in the day, with relaxing and happy lounge music. Most importantly, the staff is highly well trained, educated, and devoted to service with a smile without the attitude sometimes found in premium hotels sometimes. Mattia (spelling?), Duna, Julian were amazing. Coffee in the room a great plus! Short walk from the ferry (3 minutes!) and in the center of the action makes this hard to beat. I would only add more obvious breakfast choices (most guests just go out to great options short walks away) to make this even more perfect. We will certainly be back.
Reviewed on Jul 28, 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
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 7 - Sep 8
includes taxes & fees
8.4/10 Very good! (327 reviews)
"Great location & love Falmouth. Not the greatest place to stay though… & certainly not consummate to the price. Room & accommodations were fine, but old/poorly maintained. Hair in places, etc speak to cleanliness. Biggest issue was design/configuration of bath room where steam, condensation, spray ..."
Reviewed on Aug 8, 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! (418 reviews)
"This was our second time staying at Sea Crest. And left this year very disappointed. Our first room had a hole in the wall in the bathroom and front desk staff were not helpful or concerned with us wanting to switch rooms. The check in process was not smooth and check out was the same. We were charged ..."
Reviewed on Aug 8, 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.
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.
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.
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.
Wades Field
You can take time to visit Wades Field during your travels to Chilmark. Amble around the area's beaches or experience its 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.
Fulling Mill Brook Preserve
Enjoy an outing to Fulling Mill Brook Preserve during your stay in Chilmark. Wander the area's waterfront or simply enjoy one of its wineries.
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 $1,601 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.
