Search Vacation Homes in Shelter Island

"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "

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

"House was great and spacious, plenty of room and house is laid out nicely with living space on the third story and beds mostly on the second story. Boat was extremely responsive and helpful during the stay. The Location was great, the outdoor deck was nice to spend some time outside and relax after golf. Would definitely come back again. Thank you! "

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

"Had a great stay! Everything about the stay was perfect. Place was all that we expected and more. Host was easy to reach and very responsive. "

"Perfect getaway for a group of ladies spending a snowy night catching up away from our spouses and kids. Cozy fireplace, beautiful home, ample space and in a great location. Highly recommend!"

"Margaret is just wonderful. We felt like we were staying at a dear family member’s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"

"Beautiful home close to the Sound. Our stay was in February and just happened to coincide with a winter storm. The house was very cozy for my husband and I and our 4 teens. They had a blast watching the LR Roku big screen and eating snacks from the fully equipped kitchen playing ping pong in the downstairs gameroom (note-not really heated in the winter so chilly, but not frigid). Sleeping areas include 2 sofas in downstairs LR, 2 twin beds in upstairs room with fold down desk, 1 full in a cozy...

"Family friendly, clean and well-stocked house with nice deck and pool for entertaining. It has personality. Well stocked kitchen (note - includes french press and a pod system but you need to bring your own pods; no coffee maker or kettle at time of our stay). Plenty of spices and condiments and entertaining ware as this is also their vacation home. Conveniently located near the highway and walkable to commercial area and 10 min drive to nearest beaches (it does back up to highway so gets road...

"Beautiful classic farmhouse with all the modern amenities including high speed internet, great kitchen and brand new heating/AC so you can enjoy all the comforts of a 5 Star Resort. Conveniently located within walking distance to the Palm, Movie Theatre and the bus stop to NYC. Beverly Leopold was a very conscientious and hospitable host. Highly recommend!"

"Susan's place was perfect for my family to visit the neighborhood where I grew up! It was clean, comfortable and had everything we needed. It's also a few steps from the beach and the amenities GNB has to offer."

"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...