Vacation rentals in Shelter Island

Very nice house and locations very good beach

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!

Had a wonderful time over Easter with my family and dog. The view was exquisite and the house very comfortable. Eileen was very responsive and even had hair dryers sent over. The house was very well equipped with lots of kitchen staple goods. Just be aware there is no microwave, but there is a very nice Breville toaster oven. Also, there is a large table outside for a group, but only a small table and counter seating in kitchen inside. We didn't have any issue since the weather was perfect for us to enjoy our Easter dinner outside. Overall, a beautiful home and only minutes from Greenport and wineries.

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.

Our stay here with our family was absolutely wonderful. The house was so comfortable and spacious and the hot tub in the backyard was a real treat during the off season. The location is great for Hampton Bays beaches and a very quick drive to the popular restaurants in town. Also a nice to drive surrounding towns. Communication with Aida was excellent and she had the hot tub ready to go during check in which was much needed after a long drive. Bedrooms are spacious and the kitchen has all the key equipment to make food at home. Backyard is large and fenced in if you have any pets. We definitely will book again in the future.

Marina was a doll! The listing for her humble abode was exact and descriptive. Everything was laid out extremely clear in the guest book. The house was pristine and very cozy. Marina stocked it up with everything you could possibly need. The decor and all of the personal touches added to the homey feel. It housed my boyfriend and me perfectly. The beach is an 8 minute walk and stunning. What a relaxing getaway. Book with Marina! ❤️

Perfect getaway in Shelter Island! The pool house is as amazing as it looks in the listing :) Cute house on a beautiful, peaceful and very private green lot. Primael was very welcoming and responsive. She was also very flexible in terms of our check in and check out. Everything went super smoothly. We enjoyed our stay a lot!