Name: Summercamp
Price range: CA $326
Rating: 9.4

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

CA $1,408

per person

Jul 16 - Jul 20

found 18 hours ago

Roundtrip flight included

Toronto (YYZ) to Vineyard Haven (MVY)

9/10 Wonderful! (631 reviews)

Our room was huge and had a comforatble bed. It looked recently renovated and was clean. The bed was comfortable. It was a rainy cold day so I asked for an extra blanket. I was given the blanket and offered a space heater which was perfect. Walking distance to restaurants, pizza and sub shops, and the supermarket and ferry.

Reviewed on May 4, 2026

The Franklin Hotel Martha's Vineyard

CA $3,872

per person

Jun 28 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Vineyard Haven (MVY)

9.2/10 Wonderful! (187 reviews)

Very clean and cozy and comfortable Conveniently located walking distance to anything you needed. Only suggestion is it would have been better to have a ground level room for easier access to the outside with our dog overall ir was very nice 👍

Reviewed on Apr 27, 2026

Morgan Hotel

CA $3,589

per person

Jun 28 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Vineyard Haven (MVY)

8.4/10 Very Good! (216 reviews)

Refrigerator was broken in my room

Reviewed on May 11, 2026

Faraway Martha's Vineyard

CA $6,188

per person

Jun 19 - Jun 22

found 11 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Vineyard Haven (MVY)

9/10 Wonderful! (1,001 reviews)

Showers were not user friendly ! We were on the first floor and there was quite a bit of noise above our room! Otherwise it was a very nice experience!

Reviewed on May 3, 2026

Harbor View Hotel

CA $6,136

per person

Jun 28 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Vineyard Haven (MVY)

8.8/10 Excellent! (1,002 reviews)

The hotel location is beautiful. The building is well kept and clean. The staff was amazing! We loved our room overall but there were a few minor inconveniences: 1. The shower handle kept getting stuck and was hard to turn off. 2. We went in April and the room got very hot at night. You couldn’t change the room thermostat from hot to cold. So they told us to open the windows, which let a bee inside our room because the windows had no nets.

Reviewed on Apr 16, 2026

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

Sea Crest Beach Resort

350 Quaker Rd North Falmouth MA

Fully refundableReserve now, pay when you stay

CA $228

CA $340 total

May 25 - May 26

includes taxes & fees

8/10 Very Good! (276 reviews)

The room , was ok ! No super excellent clean !

Reviewed on May 11, 2026

Iris Hotel Cape Cod

291 Jones Rd Falmouth MA

Fully refundableReserve now, pay when you stay

CA $181

CA $207 total

May 14 - May 15

includes taxes & fees

8.6/10 Excellent! (223 reviews)

breakfast was ok

Reviewed on May 10, 2026

Summercamp

70 Lake Avenue Oak Bluffs MA

CA $326

CA $364 total

May 20 - May 21

includes taxes & fees

9.4/10 Exceptional! (1,005 reviews)

Very cute boutique hotel! Great location, centrally located for walking. Cant wait to come when it’s hotter. VTA transit bus stop Right out front which was great and the rides are free. Hotel provided free coffee, tea, and water. No elevator so prepare to get your exercise. Lovely porch with lots ...

Reviewed on May 11, 2026

See all 2,226 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.