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.
The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
per person
Oct 30 - Nov 2
found 3 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Vineyard Haven (MVY)
9.2/10 Wonderful! (149 reviews)
Nice clean property and walking distance to downtown edgartown. Only issue was shower head was not very powerful at all. But that was no big deal for me

Reviewed on Jul. 19, 2025

The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
per person
Sep 12 - Sep 17
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
7.8/10 Good! (6 reviews)
Overall a nice cozy property. Stayed there from Monday and left Friday. No complaints or concerns. Property was clean and quite. Microwave wasnt working called the office ans it was replaced within 24 hours. Will stay again.

Reviewed on Aug. 3, 2025

Morgan Hotel

Morgan Hotel

2.5 out of 5
per person
Sep 12 - Sep 14
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
8.4/10 Very Good! (164 reviews)
I only disliked the traffic. To many vehicles on the Island.

Reviewed on Jul. 29, 2025

The Richard, The Edgartown Collection

The Richard, The Edgartown Collection

3.5 out of 5
per person
Sep 12 - Sep 14
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.6/10 Exceptional! (153 reviews)
The rooms we stayed in was small but expected for a boutique . The 3 girls that attended the desk were fabulous. Beds were comfortable. It was great for a short stay.

Reviewed on Jul. 31, 2025

Summercamp

Summercamp

3.5 out of 5
per person
Sep 12 - Sep 14
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Vineyard Haven (MVY)
9.2/10 Wonderful! (1,003 reviews)
This was our first time staying a Summercamp. My granddaughters & I come every year to the Vineyard for an overnight and we were extremely pleased with our accommodations.

Reviewed on Aug. 3, 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?

 

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Chilmark Hotel Deals

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Chilmark
9.8/10 Exceptional! (51 reviews)
Excellent Location in Chilmark. Great accommodation.
"We spent two weeks on Cape Cod and Martha’s Vineyard this summer, and the few days we spent here were the best. The communication with the host reserving the property, getting great advice regarding scheduling ferries, and information on Lucy Vincent Beach was incredible! We were able to go to Lucy ..."

Reviewed on Jul. 5, 2025

Get rates
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Sep 1 to Sep 2
CA $189
CA $238 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,005 reviews)
"Restaurant new looks good!"

Reviewed on Aug. 3, 2025

Falmouth Inn
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 CA $260 per night from Sep 2 to Sep 3
CA $260
CA $376 total
Sep 2 - Sep 3
includes taxes & fees
8/10 Very Good! (145 reviews)
"Great place to stay- lots of Amenities!! Front desk staff 100/10. They were fantastic! Got an upgrade to an Ocean Access Room ( not what it’s called but close enough lol) Great time! Will be back"

Reviewed on Aug. 1, 2025

Sea Crest Beach Resort
See all 2,313 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
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Family Vacations
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What to do in Chilmark

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
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
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

CA $69
per traveller
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Chilmark

Frequently asked questions

How much does a Chilmark vacation package cost?
You'll find cheap prices from CA $851 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.