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.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
per person
Sep 14 - Sep 17
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
9/10 Wonderful! (484 reviews)
Being on a private beach was a definite plus. There were places to eat and public transportation to key locations. Very peaceful and quiet. Already asked for reservation for next year.

Reviewed on Aug. 9, 2025

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
per person
Sep 14 - Sep 17
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
9.2/10 Wonderful! (149 reviews)
We thoroughly enjoyed or stay here.

Reviewed on Aug. 10, 2025

Summercamp

Summercamp

3.5 out of 5
per person
Sep 14 - Sep 17
found 2 hours ago
Roundtrip flight included
Detroit (DTW) to Vineyard Haven (MVY)
9.2/10 Wonderful! (1,000 reviews)
Good place to a short stay

Reviewed on Aug. 10, 2025

Morgan Hotel

Morgan Hotel

2.5 out of 5
per person
Sep 14 - Sep 17
found 2 hours ago
Roundtrip flight included
Detroit (DTW) 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 14 - Sep 17
found 2 hours ago
Roundtrip flight included
Detroit (DTW) 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

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

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 $187 per night from Sep 1 to Sep 2
CA $187
CA $235 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Excellent staff and service."

Reviewed on Aug. 9, 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 1 to Sep 2
CA $260
CA $376 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (154 reviews)
"Kids enjoyed. Nightlife is lacking, we wished the indoor pool was open later."

Reviewed on Aug. 4, 2025

Sea Crest Beach Resort
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Aug 26 to Aug 27
CA $212
CA $242 total
Aug 26 - Aug 27
includes taxes & fees
7.8/10 Good! (60 reviews)
Did the trick
"Clean room, building and rooms are a bit dated. Would return, fairly priced."

Reviewed on Jul. 13, 2025

Iris Hotel Cape Cod
See all 2,299 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
Beach Vacations
Family Vacations
Family Vacations

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 $681 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.