Holiday rentals with a kayak in Shelter Island

Wonderful, quaint older home with character. Walkable to the beach/LI Sound. Very peaceful! has all the amenities you need to include the washer and dryer. John is a very responsive. caring, pleasant host. he always answered all of our questions promptly. Great value for what we needed. Thanks John.

We stayed with a large group of friends and were pleased with how close to the water we were, restaurants were in walking distance, and the kayaks were a plus!

We had an amazing time at Brian’s home. The beach was just steps away and very private to just those of the association but, most times we had it to ourselves! So serene! Thank you for a fantastic vacation.

Nicole’s home was very lovely, clean and roomy. The neighborhood was beautiful ! Very close to beaches, farmer’s markets, Magic Fountain ice cream and restaurants. Thank you

We had an amazing stay - the house is spotless clean and very well organized, the kids loved discovering the hidden nook in their bedroom. The kitchen was fully equipped and we enjoyed a wonderful lunch on the deck. It was also lot’s of fun to use the canoes with the kids. Finally, the decoration of the house was lovely and made our stay very agréable. Thank you Carrie!

This was our second stay at this lovely home. It was the perfect place to spend a week celebrating our 51st anniversary! The house itself is beautifully decorated, impeccably clean, and offers everything we could need for cooking, comfort, and leisure. We especially enjoyed the gas fireplace and the hot tub! We made good use of the local beach pass that was furnished for us. The two very close by beaches were well-maintained and very enjoyable. We would highly recommend this location and plan to make this our go to Airbnb when we are in this area. Irina is the perfect host! She is extremely responsive and reliable.

Steven and Sylvia are great hosts. The house was very accommodating to our needs. The house invited us to engage in fun activities such as roasting marshmallows, playing pool, and kayaking. The house also provided us a beautiful view of the ocean and the wildlife. We truly enjoyed our stay and wish we could stay even longer.

Noah was amazingly helpful for a long weekend we took with our two kids. He had a full size folding crib which made sleeping our 3 year old, easy. He keeps a beautiful, well-stocked home, which made it so convenient to cook some meals at home. The location is amazing, only a short drive to town and a priceless view of Fort Pond only steps away. Would love to stay here again.

We very much enjoyed staying in Meredith’s place. The cottage is surrounded by trees so it feels secluded and peaceful. The cottage is elegantly decorated; there were so many nice books around which we enjoyed checking out. Meredith was so nice and responsive. We will definitely go back.

Prachtig gelegen vakantiehuis op loopafstand van strand. Fijn huis en fijne omgeving!

Simply wonderful spot! We will try to come back! The personal touches were great. Shampoo and conditioner! Make up wipes! Plenty of toilet paper and so on. Traveling guests really appreciate those small things. Thank you!

Wonderful bay side cottage! Stayed here for a long weekend with my husband and in laws. It’s a great location!! Water views, walkable cute neighborhood, and 20 mins from some of the bigger towns (Jamesport & Greenport) Place was clean and a fully stocked kitchen made it easy to stay in and grill out.

We absolutely loved our stay in Clinton! The apartment was beautiful and clean with an amazing view. We tried lots of local hot spots and had a great swim at nearby Hammonasset. Communication and instructions were excellent. We look forward to returning!

We had a great stay! The kitchen was nicely stocked and the house was clean. Plenty of outdoor space and beds made it comfortable even for a large group!

Meghan's place is exactly as posted it is absolutely beautiful, cozy, comfortable and did I say beautiful? one of my favorite things to do was sit in front of the big windows and read. You have everything you can think of close, at least 4 to 6 minutes away. There are restaurants, super market and pharmacies. But if you are like me and also like to cook sometimes on vacation the kitchen was equipped with everything you need. Highly, highly recommend.

This is such a great, cozy place in an unbelievable location. I spent the night with my daughters for Father’s Day. We BBQ’d a feast in Erica’s backyard. Coffee in the morning literally just around the corner in the town of Westhampton. We didn’t have beach weather but the cottage was clean, relaxing, and we all enjoyed. I would definitely stay here again.