Search Vacation Homes in Shelter Island Heights

"I wanted to surprise my husband with a weekend get-away for him and five of his buds. The house perfectly fit those needs. Plenty of beds and space. Room for them to break out the Board Games hang and Mary was a wonderful partner in answering my questions and dealing with the "surprise" aspect of the weekend. It also turns out that the location was perfect with plenty of town for them to see if they felt like getting out of the house. 2 hours from NJ and Boston made it a nice mid-point for my...

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

"This may very well be the nicest house we have ever stayed in! It was spacious, clean and well stocked. It was so nice not to have to bring our own linens! We were pleasantly surprised with a hot tub. Thank you for a great stay!"

"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...

"We loved being next door to Ocean Beach."

"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...