Serene Shelter Island Getaway: House + Guest Cottage Steps from the Water

Escape to a peaceful Shelter Island retreat just moments from the water. Perfect for families and groups, this charming 5-bedroom property includes a main house plus guest cottage with space to relax, gather, and play.

The home comfortably sleeps guests with 1 king bed, 3 queen beds, and a bunk room kids will love. Enjoy three full bathrooms plus an outdoor shower, ideal after beach days and paddleboarding adventures.

Spend your days launching kayaks and paddleboards from nearby beach access just steps away, or a 10 min walk to Reel Point beach, then come home to sunset dinners on the expansive deck. Kids can enjoy the playset and finished basement entertainment room while adults unwind upstairs. Or hang on the huge deck around the outdoor fire table with s’mores under the stars.

Inside, cozy up by the wood-burning stove after a day exploring Shelter Island’s beaches, farm stands, restaurants, and nature preserves.

Located walking distance from the iconic Ram’s Head Inn for dinner or Bocci ball. This home offers the perfect balance of relaxation, adventure, and classic island charm.

Whether you're planning a summer getaway, family gathering, or quiet weekend escape, this is your home away from home on Shelter Island.