Holiday rentals in Shelter Island

Just the getaway for a peaceful autumn weekend with a wonderful water view, lovely grounds and setting. Mark is a very accommodating host and answers any questions quickly. The apartment is well supplied and a short walk to shops. A very relaxing stay!

Had a wonderful stay at Edward and Tracey’s place! Incredible lot and view of the water. Dock has a floating portion to ease access during low/high tide. Very private, nice quiet and secluded location. But also quite close to IGA (grocery), activities, and other local points of interest. House has lots of charm and had everything we needed for a multi-week stay. A great home base for your shelter island adventures! Thank you Edward and Tracey for your amazing hospitality! Would not hesitate to return to this special place.

We loved staying in Jared's beautiful house. It was clean, comfortable, and conveniently located near lovely beaches, which we and especially our grandson enjoyed; we visited 4 different ones in just a a long weekend. We ate all our meals on the deck, and the huge backyard was an extra joy to our grandson who ran around and admired the visiting rabbits and deer. Jared was especially helpful and responsive. We asked if we could arrive earlier than 4:00p, and Jared worked with the cleaners to let us come in just after 2:00p, which was much appreciated. All in all, we loved being in Jared's house and hope to go back there again next summer. We highly recommend Shelter Island and Jared's house.

A Perfect Shelter Island Escape! We had an absolutely wonderful stay at this beautiful home on Shelter Island! The house was immaculately clean, scent-free, and comfortable. The backyard is a private oasis—lush landscaping, spacious deck with table, chairs and lounges, peaceful surroundings, and a stunning pool that we enjoyed every day. Pool towels and fun floats were provided, which was such a thoughtful touch. The location is fantastic—peaceful and quiet, yet just minutes from kayaking spots and other local activities. Parking was super easy in the courtyard, and the neighborhood felt very safe and welcoming. Inside, the house is furnished with everything we needed for a comfortable and relaxing stay. You can tell the hosts really care about both style and function. Highly recommend.

Kate was a very kind, thoughtful and responsive host. She and I had been corresponding before our stay because of a personal issue that threatened to complicate our stay. She was very gracious in all of our interactions. She and her husband made us feel very welcome and at home when we arrived, and throughout our stay. The studio was just what we needed- immaculate, peaceful and private. The location was very convenient to various sites on the island. Kate even allowed us access to her dock, which was a great place to sit and take in the marvelous sunsets the island offers. We will definitely return.

I loved Nicholas's house from the moment we walked in. The home is welcoming, spacious, and comfortable whiie accommodating the four of us so well. The kitchen excelled with layout, equipment, and water and sunset views. The furnishings and artwork are tasteful and designed for enjoyment. The bedrooms are lovely with a deck facing the water in the master and very good beds! The home is much better than the photos! I am so grateful for the time I spent here with my family. I look forwarding to returning.

I don’t know what to say other than this is one of the best Airbnb’s we’ve ever stayed in! Super private, serene, and peaceful. Just what we needed! We needed a getaway so badly, and this place was the perfect medicine! The location was fantastic as well. I can’t say enough great things about our stay. The place had such a great energy, 2 fireplaces, windows that open up into a gorgeous backyard where you can listen to birds and just enjoy peace and quiet. The Weber grill was clutch, and so was the overhang, we enjoyed every square in of this property and all that shelter island has to offer. Best egg sandwiches in the country as well. Right in Shelter Island Pharmacy there’s a great little food spot. Also Star Cafe’ had awesome coffee. Ruth and Norman’s house is such a hidden gem, a little slice of heaven! Thank you both so very much, we had a fantastic time! And we will 100% be back! Thank you so much again!!!

We really enjoyed our stay at Ena and Robs well appointed quiet apartment on shelter Island. It was in a great location close to beaches and in a perfect spot to bike around the island. Everything in the apartment was of a high quality, spotlessly clean including the comfortable bed and the linens, the kitchen was well equipped, the shower very nice and there was a lovely little balcony to sit and have your coffee in the morning. The host were very friendly and open. We would definitely go back!