Search Vacation Homes in Shelter Island

"Enjoyed this house in a great location. It was perfect for attending a family wedding!"

"Our group of friends stayed at this house for a long weekend in October 2024. The house is just as good or better than the pictures in the listing. Very clean and updated inside and out. Most importantly, the bathrooms and kitchen are clean and updated. And the huge backyard with pool, hot tub, and outdoor shower takes this house to the next level. The backyard space is great for families, small groups, or anyone looking for a quiet private space to relax. The owner/manager was very...

"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "

"This home is quintessentially charming! I arrived late at night, alone. It has a charming curved drive in and there sat the wood home with a large front porch and Forrest behind it. It seemed like little house on a prairie with the porch and dormer windows. The motion lights went on immediately, which I was grateful for. There is a narrow stairwell up to 3 bedrooms, as is customary in older style homes. High ceilings and windows everywhere enhance this property. When I woke there was a family of...

"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "

"We thoroughly enjoyed staying here, short walk to town, beautiful scenery, quiet and clean. "

"We had a wonderful 2 day stay! We already knew the area……what a treat to stay so close to the beach in such a cozy cottage. Thank you!"

"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."