Luxury Long Stay Rentals in Shelter Island

Sea Aster

• 6 guests

• 3 bedrooms

Sag Harbor, Southampton

Sea Aster sits in an ideal spot for exploring beach and town life. Sag Harbor Main Street, with its restaurants, boutiques and artisan bakeries, is less than fifteen minutes’ walk away, and you can get to Haven’s Beach – a perfect spot to watch the sun set – in ten.

Sweet Cicely

• 6 guests

• 3 bedrooms

Ulster County, Woodstock

Set in 15 acres of private grounds, this modern mountain chalet in New York’s Catskills is the ultimate Upstate getaway. Inside, the place is rustic yet refined with timber vaulted ceilings, mid-century modern furnishings and a creamy colour palette.

Kennedies

• 9 guests

• 4 bedrooms

North Sea, Southampton

An idyllic escape for all the family, this waterfront home sits in the hamlet of North Sea, part of larger Southhampton, and within an easy drive of a wide selection of restaurants, boutique shops and beautiful beaches. Whether you're here for a weekend or a longer stay, you'll immediately feel relaxed in this quiet spot, surrounded by nature.