Chilmark Vacations from $726

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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.
Vineyard Harbor Motel - Private Beach

Vineyard Harbor Motel - Private Beach

2.5 out of 5
Save 100% on your flight
Price was $1,127, price is now $726 per person
$726
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Vineyard Haven (MVY)
9/10 Wonderful! (659 reviews)
It will be my go to spot each time I visit. It was great and services were excellent.

Reviewed on Jul 10, 2026

The Franklin Hotel Martha's Vineyard

The Franklin Hotel Martha's Vineyard

2 out of 5
Save 100% on your flight
Price was $1,743, price is now $1,395 per person
$1,395
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Vineyard Haven (MVY)
9.2/10 Wonderful! (195 reviews)
clean, updated nice decore in the room and common areas. Free Parking and a good location 10 minutes from town all were very positive. the down side : NO Staff! no one to check you in or out, no one to help with anything or make any recommendations. fully self service made it feel very low end unfortunately

Reviewed on Jul 1, 2026

Morgan Hotel

Morgan Hotel

2.5 out of 5
Price was $1,413, price is now $1,133 per person
$1,133
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Vineyard Haven (MVY)
8.6/10 Excellent! (233 reviews)
Excellent location and superb staff. Very helpful .

Reviewed on Jul 10, 2026

The Island Inn on Martha's Vineyard

The Island Inn on Martha's Vineyard

2.5 out of 5
Price was $1,205, price is now $1,007 per person
$1,007
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Vineyard Haven (MVY)
8.2/10 Very Good! (39 reviews)
We stayed in the townhouse. Plenty of room, 2bd and 2bths. Living with fireplace, deck and kitchen. Love the modern country decor. High ceilings with large wood beams. Would definitely stay again!

Reviewed on Jul 1, 2026

Harbor View Hotel

Harbor View Hotel

5 out of 5
Save 100% on your flight
Price was $2,620, price is now $2,244 per person
$2,244
per person
Aug 28 - Aug 31
found 14 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Vineyard Haven (MVY)
8.8/10 Excellent! (1,001 reviews)
Property was Beautiful. Only downside was there is no Elevator in the area we stayed which was a pain being on 3rd floor with a baby/carrage etc. My fault for not checking ahead of time but other than that the place was great. Close walking distance to downtown Edgartown. Staff was very friendly and accomodating.

Reviewed on Jun 24, 2026

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Stay near popular Chilmark attractions

Menemsha Beach

This serene beach offers gentle surf and a front-row seat to Martha's Vineyard's most spectacular sunsets. Purchase fresh seafood from nearby markets to create a memorable oceanside dining experience.
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What to do in Chilmark

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours

$45
per adult
Massachusetts Self-Guided Audio Tour Bundle: 10+ Tours
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

Cozy efficiency apartment/heated pool

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

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Cozy efficiency apartment/heated pool
Private Hilltop Chilmark Estate with private tennis court, gym and hot tub

Private Hilltop Chilmark Estate with private tennis court, gym and hot tub

Chilmark MA
2/10 (1 review)
Vacationing while black
"The owner agreed to let me have a few guests onsite but then became belligerent, rude, and nasty when his neighbors alleged I had an event 3 days after said date. I was told i was not welcomed in Chilmark and thrown off the property. VRBO sided with the property owner. Seems to be the practice when ..."

Reviewed on Aug 23, 2022

Get rates
Private Hilltop Chilmark Estate with private tennis court, gym and hot tub
Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $249 total per night from Jul 19 to Jul 20
$249 total
Jul 19 - Jul 20
Total with taxes and fees
8.6/10 Excellent! (285 reviews)
"Great and friendly lady that maintained our room. Front desk was difficult to reach - had to call over and over and no one would respond - the front desk girl was not that friendly- the tub would clog- bed was super comfortable - it was just ok for me."

Reviewed on Jul 11, 2026

Iris Hotel Cape Cod
See all 2,273 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.

Find the Best Chilmark Vacation Packages

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.

Chilmark Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Martha's Vineyard Airport (MVY)
Population
860
Max Temp Winter
40ºF
Max Temp Summer
70ºF
Top Sights
Marthas Vineyard Museum, Lamberts Cove Beach and South Beach

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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 $726 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.