Please contact us if you are interested in booking a month or longer stay for the 2024 summer season.

An impeccably restored and charming Victorian summer cottage originally built in 1876 and located in the heart of historic Shelter Island Heights, Gingerbread Cottage is a five bedroom, four bathroom vacation rental that is fully furnished and beautifully appointed. With over 3,300 square feet of living space to spread out, this is the perfect retreat from the hustle and bustle of city life. The property features a wrap around porch with outdoor living and dining areas in a private setting behind a mature hedge. Perfectly situated amidst the best of Shelter Island, you can walk or bike to beaches, shops, the public golf course and Mashomack Preserve.

The classic comfort of this home welcomes you with period details such as gingerbread gothic carpentry details, white picket fence, hedge arches, gabled roofs, a famous leaning tower, and plenty of nooks throughout the house to enjoy. Hide away in one of the five bedrooms, enjoy an evening cocktail on the wraparound porch looking out to Greenport Harbor, or lounge around the property with your favorite book.

When the mood strikes and you are ready to venture out, you are only a few minutes walk from the conveniently located Heights shops, restaurants, hardware stores, yoga, pilates, and nearby golf course. The Shelter Island Heights Association tennis courts are directly across the street, and the beach club is a three minute walk away.

Swing by the Shelter Island Pharmacy for basic sundries and an authentic egg cream from the “gooseneck” dispensers at its century old lunch counter. Grab coffee from Stars Cafe or takeout from Isola, with its modern take on Italian cuisine. Down the street, you can find the popular Marie Eiffel Market. All are a short walk from Gingerbread Cottage. The Sunset Beach Hotel, operated by André Balasz, with famed sunset views, and the Perlman Music Camp with world class young musicians performing camp are a ten minute bike ride. Or walk across the lawn to the North Ferry and you are an eight minute ferry ride away from the walkable main streets of Greenport village with award winning restaurants such as Barba Bianca, Frisky Oyster, Aldo’s Coffee, Bruce & Son’s, American Beech, 1943 Pizza and Brix & Rye speakeasy.

Like a pearl between the pincers of Long Island’s North and South Forks, Shelter Island’s easy, natural rhythm and pristine beauty keeps the island one of the last great beach towns in the United States.


Sleeps 10 guests

Five bedrooms, four bathrooms

Indoor dining room, living area, and great room

Outdoor entertaining and hang spaces including wrap around veranda and balcony overlooking Greenport Harbor

Stocked kitchen, and outdoor gas BBQ

Complimentary WiFi

Washer & dryer

Centrally located in the historic Shelter Island Heights neighborhood

Guests receive access to Shelter Island Heights Property Owner’s Association tennis courts and beach club

Two week minimum stay during summer season; Nightly rental available after Labor Day

Porch furniture and cushions removed after October 31

SI Heights Association Beach Club closed after Labor Day; tennis court closed in autumn TBD

2022-S-0002