Name: Summercamp
Price range: CA $336
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 1 day 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

Faraway Martha's Vineyard

CA $4,114

per person

Jun 18 - Jun 21

found 3 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) 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

The Franklin Hotel Martha's Vineyard

CA $5,664

per person

Jul 2 - Jul 6

found 10 hours ago

Roundtrip flight included

Sault Ste. Marie (YAM) 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 $5,669

per person

Jul 2 - Jul 6

found 10 hours ago

Roundtrip flight included

Sault Ste. Marie (YAM) to Vineyard Haven (MVY)

8.4/10 Very Good! (216 reviews)

Refrigerator was broken in my room

Reviewed on May 11, 2026

Harbor View Hotel

CA $7,124

per person

Jul 2 - Jul 6

found 10 hours ago

Roundtrip flight included

Sault Ste. Marie (YAM) 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 17 - May 18

includes taxes & fees

8.6/10 Excellent! (225 reviews)

The 1st room we were assigned had ants and a chemical smell. I thought perhaps it was their cleaning chemicals but in retrospect it was potentially insect spray. The staff did accommodate us quickly and moved us to another room. The 2nd room was at least bug free but.... it had plaster patching issues ...

Reviewed on May 11, 2026

Summercamp

70 Lake Avenue Oak Bluffs MA

CA $336

CA $376 total

May 26 - May 27

includes taxes & fees

9.4/10 Exceptional! (1,008 reviews)

Staff Was Super Friendly And Helpful For My Work Trip To Help Me Make The Most Of Being There While Still At Work. Beautiful Spot As Well!

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.