Chilmark Vacation Homes

A dock with boats, a small wooden structure, and a forested shoreline.

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Our top choices for Chilmark holiday homes

Ocean view, FREE BEACH PASS. Short drive to multiple beaches and water park!

Fairhaven

Zachary S.

HK$4,056 total

includes taxes & fees

15 Jul - 16 Jul

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Falmouth

Gokul K.

HK$7,558 total

includes taxes & fees

7 Jul - 8 Jul

Backyard Retreat / 5 Min > Beach & Main St

Fairhaven

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Falmouth

Lisa F.

HK$6,948 total

includes taxes & fees

16 Jul - 17 Jul

serene wooded 3-bedroom house West Tisbury deck, screen porch and outdoor shower

West Tisbury

HK$7,341 total

includes taxes & fees

11 Jul - 12 Jul

A NOSTALGIC SPACE! Your Martha's Vineyard Getaway!

Oak Bluffs

Louis R.

HK$10,259 total

includes taxes & fees

30 Jul - 31 Jul

Vineyard Haven Family Beach, Fire Pit & Garden View

Tisbury

Jane H.

HK$12,765 total

includes taxes & fees

7 Jul - 8 Jul

Chappy - Family Beach House

Edgartown

Carmin R.

HK$10,758 total

includes taxes & fees

26 Jul - 27 Jul

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Top Chilmark Hotel Reviews

Vineyard Harbor Motel - Private Beach

8/10 Good

"This was my second stay! I love the great location, private beach and friendly hotel staff! There are excellent restaurants and FREE public transportation STEPS away. A cruise ships was docked a few feet away from their beach. While lying on their private beach, I discovered a Horseshoe crab in the sand, which I've never seen before. I did have an issue with the AC in my unit this trip. We didnt have it on automatic, nor a timer. However, it kept shutting off itself, and the room had gotten hot quickly before it came back on. Since we were out all day into evenings, and staff leaves at night, we didnt inform them. Overall, I definitely will stay here again!"

The Cape Club Resort

10/10 Excellent

"This was the perfect choice for us. We knew we would be driving to different areas of Cape Cod and day tripping to Martha’s Vineyard, so quaint/walkable wasn’t the priority. The staff was super welcoming and helpful, room was immaculate, spacious, comfortable bed, balcony for fresh air…great food on site which we took to go to relax in the room after a long day traversing MV. It’s too new for tons of reviews, but don’t let that stop you, grab it while you can!"

Sea Crest Beach Resort

8/10 Good

"convenient short drive from Boston with less traffic over Bourne Bridge. great location with pristine calm and warm water beach. great staff helping get settled on the beach with chairs and umbrella. fortunate to select room with patio first floor which was convenient. rooms were fine nothing scary or amazing. service at bar was quick. food services were slow and basic. great value"

Admiralty Inn & Suites - a Red Collection Hotel

10/10 Excellent

"Found this great spot in Falmouth, an older property (you can see that they have been maintaining it) but the rooms were spotless rooms. The Inn is located on a main road but close to downtown, perfect location. We enjoyed our quick trip and intend to go back!"

Green Harbor Waterfront Lodging

8/10 Good

"Checking in was easy. The person at the reception was kind and helpful. Our room was smaller than expected but tidy. It was supposed to sleep 5 (1 king bed and a pull out couch). There weren't extra linens and the office was closed by the time we noticed. Some of the outlets did not work so we all had to share chargers to juice up the electronics. On a brighter note, the room was lake side and there were outdoor tables with umbrellas. The neighbors we encountered were friendly and the pool was excellent. We liked that it started at 3 feet for those who cannot swim. The water was warm and clean. It is great that it is also pet friendly. We would stay again but will be a little better prepared."

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