Holiday rentals in Shelter Island

The Cottage was a perfect blend of rustic and modern, thoughtfully appointed and had everything we could think of. Our big plus was the trust and no hassle from the hosts to include our beloved big dog. My husband and I came out to the North Fork for our October babymoon. The Cottage town area is very serene during the fall season, with most activity around the pumpkin farms. Our favorite things to do—take the dog down to the bulkhead in the mornings, spend the afternoons on a nature walk/winery nearby and nights at a local restaurant. Cons but not dealbreakers: Spotty internet often went in/out. Persistent fruit flies all throughout house, traps didn’t help. The listing advises of the Main House rental, we found it not very private to the closeby Cottage. With big glass doors and sheer curtains, you’re in plain view to the House at night. It felt too intimate for our preference to share the small beach with strangers 15 ft away, esp with their kids and our dog.

We were truly lucky to have found William home. It was spotless, he was extraordinarily friendly, the house was just amazing. For the two families that were there, it met every need we had, it was well appointed, and we could not have asked for more.

Very nice stay in Guilford. We enjoyed our stay in the Red House very much, it was extremely relaxing. We loved the fireplace and lots of rooms to relax in, and the morning walks to the water were so beautiful. The house is well equipped, had everything we needed.

Our stay in West Haven, CT, was absolutely wonderful. The Airbnb was immaculate, well-furnished, and perfectly situated near a lovely beach. The cozy ambiance and thoughtful amenities, like fresh linens and a fully equipped kitchen, made us feel right at home. The outdoor space was a lovely bonus, providing a peaceful spot to relax and enjoy the beautiful surroundings. The close proximity to the beach was a highlight of our trip, allowing us to enjoy morning walks and sunset views with ease. The location also offered convenient access to local attractions and dining options, making our stay even more enjoyable. We highly recommend this Airbnb to anyone visiting West Haven for a relaxing and memorable getaway. Adam was a tremendous host!! We will be back for sure!

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.

Perfect weekend getaway spot with a wonderful backyard. The hot tub was a treat and the rooms were clean and spacious. Highly recommend!

Marina has my heart!! ❤️ What a lovely host, the place was SO perfect, so cozy and clean. Marina was there within 5 minutes answering any questions I had. I can’t wrote enough about my stay and this cozy space! A++++ Thank you, sweet Marina.

Maria was an amazing host! So caring, responsive, and proactive about everything, from checking in to recommendations! The place was beautiful, especially the lake in the back. It's in a quiet, peaceful neighborhood and close to all the beaches and great restaurants nearby. Overall, it was an amazing stay, I would absolutely stay there again! :)