Shelter Island vacation rentals

We decided on the cottage for a winter sister getaway and it was exactly what we were hoping for and more! The beach is a short walk down the driveway, and we were surprised by the extent of the view from house. You can see more than a bit of the ocean through the trees and homes in front of the cottage, more view than we anticipated!). You can even hear the waves crashing on the beach from the house. The kitchen was well equipped for cooking. We used the fireplace each night and the radiators worked beautifully to keep us warm in our rooms. We were an easy drive from all of the small towns we wished to visit. The hosts were kind and helpful when us Floridians were unsure if two separate snow events might impact our arrival and departure; it all worked out and the roads were well-cleared! I would love to return for a visit in the summer!

Ed was great at communicating, house was everything we could have asked for. Would definitely book again!

This was my second time staying here, and probably won’t be the last. A perfectly wonderful Hamptons home, with a beachy, rustic charm. It’s close to all, yet on a quiet street with a great backyard. David is a fantastic host, everything was spelled out clearly and the home was spotless.

Location was perfect for us- easy to find and close to things that are important to us (family in area, beach, shopping). Fenced yard made bringing our little dog that much easier- especially during the rainy day! Kitchen was well stocked thankfully as we were cooking Thanksgiving dinner (but not well stocked in the casserole dish, baking tin department-- which is usually not an issue for most people!). Decent coffee was supplied with a Keurig. Beds were comfortable. Everything was clean. I liked that he didn't leave a long list of what we needed to do before leaving as that is often a hardship when trying to leave a house with kids before a long drive. I would definitely stay here again.

Eduard’s place was wonderful! 6 of us gathered for the new year and there was plenty of room for all of us and one pup. The hot tub was excellent, and the landscaping was beautiful. The surrounding area was quiet and lovely. The den was a great area to relax and play games in. We’d definitely recommend staying here.

We had an INCREDIBLE stay! We went for my sisters bachelorette party and it was perfect. It made me want to book again in the summer! I was initially worried about space, but everyone fit perfectly. Paula was very accessible and easy to work with:) 10/10 recommend.

We had a wonderful time! Highly recommended!

I had an amazing experience staying at this Airbnb! Luz, the main host, was absolutely wonderful—so kind, welcoming, and incredibly helpful throughout my stay. She went above and beyond to make sure I had everything I needed and even took the time to recommend some great local spots to visit. Her hospitality truly made this stay special. David was also fantastic so professional and accommodating. He made everything so easy, from check-in to answering any questions I had during my stay. It’s clear he takes pride in ensuring guests have a great experience. The space was spotless, beautifully decorated, and just as described in the listing. It felt so cozy and inviting, and the little details, like the complimentary snacks and toiletries, made all the difference. The location was also perfect. I couldn’t have asked for a better stay. Luz and David are a fantastic team. I highly recommend this Airbnb to anyone looking for a comfortable, welcoming, and enjoyable experience.

We had a great stay. The house was warm and inviting. Very peaceful and quiet. Plenty of room for the family. Very easy to get to and very close to downtown. I would highly recommend!!! Steve was very friendly and responsive to all our needs!

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.

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.

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!

I spent the weekend at Eric's house with my parents and it was absolutely perfect. Such a bright, comfortable house in an incredibly convenient location. ~5 minute drive to Sag Harbor town, ~15 minute drive to Sagg Main beach, and ~10 minute drive to Wolffer Estate. We experienced a few issues upon check in (had some trouble working with the electronic door lock, no toilet paper), but Eric personally called me and made it his business to resolve it. He really demonstrated being a great host and making sure that we had no issues. I would definitely stay at Eric's property again, it truly felt like a home away from home.

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.

Staying at this home on Airbnb was a fantastic experience! The host was incredibly friendly and welcoming, making sure we had everything we needed for a comfortable stay. The home was beautifully decorated, clean, and spacious, with all the amenities we could ask for. The location was perfect, close to local attractions and restaurants. We enjoyed our time here and would highly recommend this to anyone looking for a memorable stay.