Chilmark Vacations from $552

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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.

The Latest Chilmark vacation packages

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
Save 100% on your flight
Price was $778, price is now $552 per person
$552
per person
Oct 12 - Oct 16
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9.2/10 Wonderful! (152 reviews)
It’s a nice boutique hotel but it is in the middle of no where the restaurant across the street is less than desirable. The walk to town is too long on a main street

Reviewed on Aug 16, 2025

Summercamp

Summercamp

3.5 out of 5
Save 100% on your flight
Price was $974, price is now $672 per person
$672
per person
Oct 12 - Oct 16
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9.2/10 Wonderful! (1,001 reviews)
My husband and I celebrated our 46th wedding anniversary. The hotel surprised us with silk rose petals, champagne, and balloons. We really appreciated it. The only complaint is the people above our room(203) were very noisy into the wee hours of the night and early morning.

Reviewed on Aug 22, 2025

Morgan Hotel

Morgan Hotel

2.5 out of 5
Save 100% on your flight
Price was $790, price is now $603 per person
$603
per person
Oct 12 - Oct 16
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.4/10 Very Good! (167 reviews)
great location, small but modern

Reviewed on Aug 19, 2025

Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
Save 100% on your flight
Price was $1,149, price is now $906 per person
$906
per person
Oct 12 - Oct 16
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
9/10 Wonderful! (1,001 reviews)
Beautifully decorated and nice workspace. Staff was not helpful with baggage at check-in. For the price, the toilet paper was cheap and no slippers. It was very nice that they allowed you to use the pool and property after the 11am checkout.

Reviewed on Aug 9, 2025

Harbor View Hotel

Harbor View Hotel

5 out of 5
Save 100% on your flight
Price was $1,231, price is now $1,032 per person
$1,032
per person
Oct 12 - Oct 16
found 2 days ago
Roundtrip non-stop flight included
Atlanta (ATL) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,000 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

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Discover the most popular places to visit in Chilmark

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.

Menemsha Beach

Lucy Vincent Beach

If a restful vacation is part of your travel plans, Lucy Vincent Beach might be the perfect place to seek out during your trip to Chilmark. Take in the festivals and sunsets in the area.

Lucy Vincent Beach

Chilmark Chocolates

Enjoy an outing to Chilmark Chocolates during your stay in Chilmark. While in this walkable area, you can savor the wineries.

Chilmark Chocolates

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

$130
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

$50
per adult
Massachusetts Highlights: Freedom Trail, Salem & More Tour
Massachusetts Self-Guided Driving and Walking Tours Bundle

Massachusetts: Smartphone-Based Audio Tour Bundle

$50
per traveler
Massachusetts: Smartphone-Based Audio Tour Bundle
See all activities in Chilmark

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
$150 nightly
The price is $170 total per night from Sep 8 to Sep 9
$170 total
Sep 8 - Sep 9
Total with taxes and fees
7.8/10 Good! (1,000 reviews)
"The hotel is convoy to down town, clean and seemed updated since last visit. The price was right."

Reviewed on Aug 21, 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
$221 nightly
The price is $253 total per night from Sep 1 to Sep 2
$253 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (177 reviews)
"."

Reviewed on Aug 21, 2025

Sea Crest Beach Resort
Faraway Martha's Vineyard

Faraway Martha's Vineyard

3.5 out of 5
23 Kelly Street, Martha's Vineyard, Edgartown, MA
$709 nightly
The price is $792 total per night from Sep 1 to Sep 2
$792 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Very well updated"

Reviewed on Aug 21, 2025

Faraway Martha's Vineyard
See all 2,268 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.

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 1 mile (2 km) 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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Frequently asked questions

How much does a Chilmark vacation package cost?
You can snap up a vacation package to this destination from $552 on Expedia. However, how much your vacation to Chilmark costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Chilmark?
If you'd like to snag a cheap Chilmark vacation package, consider traveling in November, December and January. You'll usually find lower rates on flights and hotels during these quieter months — perfect for travelers wishing to save money.
How many days is enough for Chilmark?
The ideal duration of your Chilmark vacation depends on what you'd like to do. Usually, a handful of days to a week will give you time to visit all the top sights and discover some hidden spots along the way.
Is it worth booking a vacation package to Chilmark?
Chilmark offers everything you need for a wonderful getaway. Get your Chilmark vacation off to a flying start by exploring popular attractions like Menemsha Beach.
How to find the best Chilmark package deals?
Landing a cheap Chilmark package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Chilmark package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Chilmark vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging stays and flights separately. Better still, you can personalize your Chilmark getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chilmark?
If you've got your Chilmark travel dates finalized, book as early as you can to snap up some awesome deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Chilmark?

  1. Choose your travel dates: What you want to do in Chilmark and your preferred season will help you decide when to travel.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Chilmark.
  3. Use Expedia's trip planning tool to discover Chilmark: Research every aspect of your trip to Chilmark with this handy planner. Invite your friends and family to collaborate on a group trip, search for stays or things to do and make bookings.
  4. Decide how many days away: Start by listing all the activities and sights you want to get to in Chilmark. Then, estimate how long you'll need for each, along with any travel time.
  5. Combine your airfare and accommodations: After you've settled on your dates and duration, book the right Chilmark vacation package for you.
  6. Add on excursions and experiences: Have a look at our travel guide to find some fun things to do in Chilmark. Book tickets or make reservations in advance to save time and avoid the hassle of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Chilmark vacation packages?
Your Chilmark getaway is meant to be an escape from your daily routine, not a reason for money worries. So to give you more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.