Max 7 guests 3 bedrooms 1.5 baths No pets 
What our guests are saying...
This is a top guest review for this property
Our stay was everything we expected, and we had a great time. The house has a few quirks, but it was charming and ideal for our family with grown children. The location was quiet and private, we saw deer and bunnies in the yard and really enjoyed being off the beaten path. The beds and living room furniture were very comfortable, the AC and wifi worked great and there was plenty of hot water. There were a few things in and around the house that need maintenance, plus the yard has overgrown quite a bit. It would be a hard place to stay if you had very small children or older people, but it was perfect for us. We gave it 5 stars despite the things that need repair because they weren't an issue for our family, and we truly enjoyed the house and the location. This is a great place if you are looking to get away and have a nice quiet vacation in a beautiful spot on the island.
Jill W. Jul 2025
Read more

OVERVIEW

Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

Named for the sea breezes that circle this charming and unique home, the Whistling Hill House is nestled alongside the Martha’s Vineyard Land Trust, ensuring a private and peaceful vacation. A five-minute walk takes you to Lobsterville Beach for swimming in the sound. Come home and wash off salt water and sand in the outdoor shower, then sunbathe on one of the two decks.

Window AC units are available in each bedroom, the living room, and the common room.

Ocean swimming is an eight-minute drive away at the beach, rated one of the 20 most beautiful in the world - the Moshup Public beach, with the spectacular-colored cliffs as background setting and the Gay Head Lighthouse overlooking the scene.

For the best young children’s swim and play time, a saltwater pond is another short drive away. Menemsha Pond is also a nice place for a birding walk or a longer walk along beautiful Lighthouse Road. The traditional fishing town of Menemsha, still an active place to pick up the freshest fish available on the island as well as antiques and other niceties, is of course accessible by car - but is also easy to get to via the five-minute bike ferry operated between Aquinnah and Menemsha.

The Orange Peel Bakery is a Wampanoag-owned local bakery with an outdoor brick pizza oven, extraordinary homemade pies, and many other goodies. A 10-minute walk or three-minute drive up Lobsterville Road (in the opposite direction of the ocean), this spot often hosts summer pizza nights where folks decorate their own pies with various toppings.

At the top of the Aquinnah Cliffs, above the ocean beach, is a historic lookout where you can watch the sunrise and sunset with breathtaking views. The Aquinnah Shop Restaurant features one way of doing this while dining, but there are also a group of small shops and eateries which line the road to the top of the Cliffs. World-class clam chowder is available (comparing and rating the best chowder is an annual activity)!

Insights into local Wampanoag history and ongoing life can be found at the Aquinnah Cultural Center (a mini-museum), where summer workshops have included craft-making sessions, artist demonstrations, and book launches.

As noted, walks from easy to strenuous can be had just from the house - along Lobsterville Beach Road around the peninsula, to the ocean beach, cliffs, and lighthouse, or Menemsha Pond and the docks to the ferry to the town of Menemsha.

THINGS TO KNOW

  • 5 window AC units are available, one in each bedroom, one in the living room, and one in the common room.

  • Streaming is available using your own accounts.
  • The woodstoves are not operational.
  • The full kitchen does not have a dishwasher.
  • No pets are allowed at this vacation rental.
  • Parking notes: There is free parking available for 2 vehicles.

State/province tax number: C0338921040

You must be 21 years or older to rent this property.

AMENITIES

Features

Washer/dryer : Private

Heating & cooling

Central AC

Partial AC

Kitchen & dining

Fridge

Microwave

Stove

Media

Internet

TV

Cable

Wireless router

Netflix streaming

Outdoor

Deck

Beach towels

Firepit

Location

Aquinnah, Massachusetts, Home

(Exact address will be provided after booking)
Map showing the location of the Unit

Rating

3.18
Worry-free cancellation
Get a full refund if you cancel within 24 hours of booking*
24/7 guest support
Count on care—just a call, text, or email away
Best pricing
Book directly for the lowest rates