In the Heights
Squire Chase House sits in the heart of Shelter Island Heights, the Victorian quarter above Dering Harbor laid out in the early 1870s as a Methodist camp-meeting community. The plan survives: winding lanes following the hill instead of a grid, shingled cottages under old trees, and the harbor at the bottom of the walk.
On foot
The North Ferry from Greenport lands at the foot of the Heights, and the Marie Eiffel market sits along the same walk, which makes this one of the few stays on the island that genuinely works without a car. Arrive on foot from the ferry, provision at the market, and the island’s beaches and back roads are a bicycle problem rather than a parking one.
The space
The rooms run wide open and loft-like, an unusual volume for the Heights’ cottage stock, and the house sleeps six across three bedrooms.
It books by the night on Airbnb, two nights minimum, at $832 a night through the winter and spring and up to about $944 in high summer. A full week is priced lower, around $750 a night.
