Vacation rentals with a kayak in Shelter Island

We had a wonderful stay at Harbor House. The view of Napeague Harbor is gorgeous and the sunsets are just next level spectacular. The kitchen is well equipped for cooking in and the furnishings are very comfortable. The location is great halfway between Amagansett and Montaik. We have rented so many homes over the years, but Rod’s house is by far in the most gorgeous setting. We cannot wait to return.

Bill’s place provided a wonderful location for our family of seven to spend our Thanksgiving holiday. The house was clean, uncluttered, and comfortable in every way. The kitchen had everything we could hope to find for meal preparation. The two sitting rooms provided delightful spots for reading, conversation or catching up on the television news. The upstairs bathroom was especially room and well-appointed. While it was winter when we visited, we could tell that this house would be a truly marvelous spot during the summer months as it had a great back deck and was truly only a hundred yards or so from a beach on the Long Island Sound. While it may not be the first choice of those who are on a tight budget, we recommend this home highly.

My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!

We thoroughly enjoyed our stay and would definitely book again ! Close to the many wineries and cute towns, and peaceful and comfortable to come back and relax at. We enjoyed the fire pit , the view from the dock of the changing tree colors and the flow of the kitchen. ❤️

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.

Petra’s house is in the most beautiful spot on a small lake and a stones throw from the beach. This was our second year there and we hope to be back. The house is stocked with everything you need to feel comfortable including great bath products, kitchen, equipment, and toys and books. I never felt uncomfortable in her house. This was a wonderful family week in heaven.

Maria's place is gorgeous, just as described. It is located in a tranquil neighborhood and right next to the lake, just 10 to 15-minute drive from the Main St of East Hampton / Sag Harbor. They have an outdoor grill and kayaks on site which is perfect for a group of friends. My friends and I had a blast there and I would recommend it !

We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.

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 adult daughters and I thoroughly enjoyed our stay in this peaceful cottage! The cottage was cozy, comfortable, and just the right size for the three of us. The house and kitchen had all the essentials and we enjoyed the treats and complimentary food that Gail provided. We relaxed and strolled down to Indian Cove and Barbra Pine Memorial beaches. Overall, we had a fantastic stay and highly recommend!

We lived our stay at Carey’s place and plan to come back next year. Amazing location if you want to relax and take a few days away from the city. The house is very cozy and comfortable with a great backyard facing the water. Thanks Carey!!

Returning guest, we had a wonderful weekend at Michelle's idyllic home. Plenty of space for our two families and 3 kids. The kids love having their own space in the "she shed" while the adults enjoy the lakeside views from both the yard and inside the spacious living area. The house is always immaculately clean. Beds and other furnishings are comfortable, and the house is an easy drive to everything the North Fork has to offer. We look forward to returning (again!) soon.

My stay at Chris and Ann’s listing was the perfect last stop on my stay in CT……beautiful, welcoming accommodations enhanced by the natural, peaceful, setting of the salt marsh and wildlife. It’s absolutely a favorite place the next time I’m visiting CT.

Everything about this stay was as near too perfect as possible. First Sean was proactive, quickly responded to any questions and his pre-visit communications were comprehensive. The pictures accurately describe the house but in reality, they do not do it justice. There are water views from every window. The place and views are amazing!! It is just what we were looking for, on the ocean, private and peaceful. Short drive to the village with shops and restaurants. Highly recommend for a couple who is looking for an escape, you will not be disappointed

We had a wonderful stay at Daniel’s home in Cutchogue. It was our second stay at one of his properties, and it did not disappoint. The house is just as described, clean and well stocked, and makes for a wonderful landing spot when exploring the North Fork.

Thank you !! We enjoyed our stay. The home is lovely and the area was so convenient to all ! The airport is 7 minutes away. Def would stay here again. Thanks again