Ram Island on Shelter Island: House + Cottage, Steps from the Water, boat access

Two houses. Water views. Kayaks included. Steps to the beach.

This 5-bedroom Shelter Island compound — a charming main house plus a private guest cottage with its own bath and kitchenette — is built for multi-family getaways. Come together for sunset dinners on the expansive deck, then retreat to your own space at night. Grandparents, in-laws, or the friends-with-kids crew get real privacy in the cottage; everyone else spreads out across the main house.

Sleeps 10: 1 king, 3 queens, and a bunk room for the kiddos. Three full baths plus an outdoor shower for rinsing off sandy feet after the beach.

Your days here: Grab the kayak or paddleboard, they're included, and launch from beach access just steps from the door, or take the 10-minute walk to Reel Point. Explore Shelter Island's farm stands, nature preserves, and restaurants, then stroll on a walk to the iconic Ram's Head Inn for dinner and bocce. Have a boat? access it right in front of the house. Let us know if you need a mooring.

Your evenings: S'mores around the fire table under the stars. Kids downstairs in the finished basement entertainment room or out on the playset; adults on the deck with a glass of wine and a water view. On cooler nights, cozy up by the wood-burning stove.

The practical stuff families actually care about: A/C throughout, fast wifi, full kitchen, and room for two families to vacation together without living on top of each other.

Summer reunion, fall long weekend, or a quiet off-season escape — this is the rare Shelter Island rental that gives your whole group space to gather and space to breathe.