Holiday rentals in Shelter Island

I recently had the pleasure of staying at a charming Airbnb in Sherley. and it truly exceeded my expectations! From the moment I arrived. The check-in process was seamless. The host provided clear instructions. The apartment was impeccably clean, beautifully decorated, and well-equipped with everything I need. The location could not have been better! Situated within walking distance to local attractions, restaurants, and public transportation, I found it easy to explore.

Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!

My family and I loved staying at Gail’s place! We grew up in Madison and were back for a visit. It was such a great place and allowed us to re-live many fond memories of growing up in the area!

We had another great stay at Claudia's place! This was our third visit to this location, and likely not our last. Thank you!!

We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!

Beautiful home with lovely views. Great kitchen for cooking. We had 8 of us and the house was spacious and welcoming for the group.

We needed a dog-friendly ranch style to home with three bedrooms and two bedrooms close to Sayville, where we would be celebrating Thanksgiving. I was lucky enough to find this rental which was clean, comfortable and ideal for our two-night stay. Adam was attentive and easily accessible via text. I would highly recommend this lovely home.

A wonderful spot and wonderful host. Everything was cheery and thoughtfully done. I knocked off a star for the price mostly because I wasn't anticipating how expensive it is to get around by Uber in the area, and to find an accessible grocery store - otherwise necessary to have a car. Ended up ordering UberEats... my mom was at another Airbnb down the road and the difference in how we were treated as guests was astronomical. Marina did not charge me for having my little dog, there was a little firewood for us to use, fresh coffee and tea, and all the amenities! Marina was also very responsive and kind, and left a very helpful note about whether the beach is public or not. 100% recommend. In contrast, my mom felt badly treated by the host, the place was poorly kept and she felt it was way overpriced in comparison to mine (Marina's). Good thing she was able to come here during the day, and we spent most of our time here, in the yard or the short walk to the beach.