Vacation Home Management Vacasa unlocks the possibilities of how we enjoy vacation homes. We take care of managing our homeowners’ vacation houses so they can have peace of mind (and their home when they want to). And our guests book vacations confidently knowing they’re going to find exactly what they’re looking for without any surprises. Each vacation home is always cared for by our professional local teams who implement our high cleanliness and maintenance values, while the hands-off tasks of vacation rental management--marketing, filing taxes, and maintaining a website--are handled by a specialized central support team. Our passion and focus remains true: to empower our homeowners, guests, and employees to invest in vacation.

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. 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. WHAT’S NEARBY 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.

No dog(s) are welcome in this home. No other animals are allowed without specific Vacasa approval. Parking notes: There is free parking available for 2 vehicles. Air conditioning is only available in certain parts of the home. Damage waiver: The total cost of your reservation for this Property includes a damage waiver fee which covers you for up to 3,000 dollars of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. More information can be found from the "Additional rules" on the checkout page. Due to local laws or HOA requirements, guests must be at least 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.