House in Shelter Island, NY
10 guests · 5 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area
About this house rental
Two houses. Water views. Water toys included. Steps to the beach.
This 5-bedroom Shelter Island compound — a charming 3 bedroom main house plus a private 2 bedroom 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.
Sleeps 8-10: 1 king, 3 queens, and a bunk room for the kiddos. Three full baths plus an outdoor shower.
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 for a small fee.
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.
This 5-bedroom Shelter Island compound — a charming 3 bedroom main house plus a private 2 bedroom 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.
Sleeps 8-10: 1 king, 3 queens, and a bunk room for the kiddos. Three full baths plus an outdoor shower.
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 for a small fee.
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.
Amenities at Charming Shelter Island House + Cottage, Steps from the Water, boat access
Non-smoking
Pets allowed
Family friendly
Map of Shelter Island, NY
$$$$
Top rated by guests
Don't miss out! Price and availability may change
