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 2 - Oct 5
found 19 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

Summercamp

Summercamp

3.5 out of 5
per person
Sep 8 - Sep 11
found 22 hours ago
Roundtrip flight included
Ottawa (YOW) to Vineyard Haven (MVY)
9.2/10 Wonderful! (1,000 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

Morgan Hotel

Morgan Hotel

2.5 out of 5
per person
Sep 8 - Sep 11
found 22 hours ago
Roundtrip flight included
Ottawa (YOW) 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 8 - Sep 11
found 22 hours ago
Roundtrip flight included
Ottawa (YOW) to Vineyard Haven (MVY)
9.6/10 Exceptional! (155 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

Harbor View Hotel

Harbor View Hotel

5 out of 5
per person
Sep 8 - Sep 11
found 22 hours ago
Roundtrip flight included
Ottawa (YOW) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
The Harbor View Hotel is exactly what holiday dreams are made of. The property is absolutely stunning, beautifully maintained with breathtaking views and elegant charm throughout. From the moment we arrived, the staff went above and beyond. Everyone was warm, attentive, and incredibly polite, making us feel truly welcomed. The entire hotel smells amazing, like a luxury spa. Our room was spacious, beautifully decorated, and spotlessly clean. Did I mention how gorgeous the entire property is? Our trip to Martha’s Vineyard wouldn’t have been half as magical without this hotel. It was truly the highlight of our stay. This is hands down the place to stay when visiting the Vineyard. I already can’t wait to return!

Reviewed on Jun. 26, 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.

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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 $186 per night from Sep 1 to Sep 2
CA $186
CA $234 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,014 reviews)
"Clean"

Reviewed on Aug. 4, 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 $259 per night from Sep 1 to Sep 2
CA $259
CA $375 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (150 reviews)
"Kids enjoyed. Nightlife is lacking, we wished the indoor pool was open later."

Reviewed on Aug. 4, 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
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Beach Vacations
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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 $178
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 $895 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.