Pet-friendly vacation rentals in Shelter Island

Everything was perfect. Peaceful neighbor. The host was helpful & responsive. I definitely recommend this property, will come again!

Good location,very good communication, house very clean everything works!!!!! Thank you very much

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!

It was a lovely stay. Great location. House felt like a home and had great vibes.

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

We were gathered from around the country for my Mother s Memorial. It was such a pleasure to stay in such a peaceful environment, as emotions were high. It was healing. Beautiful home, and all directions were clear. If it had been a little later in the Spring and the weather warmer, it would have been even better. I highly encourage anyone to stay and enjoy what the area has to offer in Gregory's beautiful home. You will have a wonderful vacation!

We had such a wonderful stay here over New Years. Like many other reviews have stated, pictures do not do this home justice. It’s so much larger and more spread out than we expected. Perfect layout for two couples where we each felt like we had our own place, with plenty of cozy spaces to hang out too. The kitchen is SO well equipped for anything and everything. Beds and sofas were super comfortable and the we loved all of the charming touches of this historical home. The location is fantastic too. Walking distance to everything you could need and a quick drive to so many beautiful areas. I can imagine spending hours in the backyard when the weather is warmer too!

Madelaine’s cottage was the perfect location for our weekend in Water Mill! The house was cozy with a spacious and private backyard. The location is centrally located, and we were even able to walk to and from breakfast and the farmers market. I would recommend the cottage and would absolutely stay again!

Marta’s place was the perfect getaway for my family. The bedrooms were large with comfortable beds. The kitchen was huge with high end appliances, and the yard was a dream for our young dog. Lovely surroundings in the woods but close to town for shopping and restaurants. Truly an unforgettable experience!

We had a wonderful time in this beautiful home that is in an idyllic Hampton's setting. Ashton was a great host and for sure we will be back.

The house is beautiful, looks like photos. Stephen is a great host! Overall great stay, could not recommend more!

Christine tiene un lugar maravilloso, tranquilo muy lindo y pensó en absolutamente todo para que uno se sienta cómodo y que no hiciera falta nada, había de todo lo que uno llegara a necesitar en la casa y también para los niños. Es una casa muy completa, cuenta con todo y seguridad para los niños. Pasamos unas vacaciones increíbles en su casa con nuestros hijos definitivamente regresaríamos sin pensarlo. Muchas gracias por todo!!

I was in Dion’s place with my family we really enjoyed the time we spent there,everything was perfect the pool was something that my kids enjoyed a lot, and hopefully we will come back again, for sure I totally recommend his house if you want to go and have a couple days of fun and relax thank you again Dion.

My stay here was phenomenal! From the host’s response time, down to the amenities that were placed throughout the house. As soon as you walk in, it felt like home. The house is spacious and highly functional. The design of the house offers a perfect blend of modern mixed with nostalgic elements. The best stay by far. Would love to book again!

Head of the Pond House was in such a beautiful peaceful setting and was exactly what we needed! Quaint, beautifully decorated, cozy, and thoughtfully stocked for a very relaxing stay. Monika was super proactive and helpful with recommendations and left us lots of local yummies. The birds and the sights on the pond (ice sailing!) were lovely. Highly recommend the cottage to take in all that the Hamptons has to offer in a peaceful and tranquil setting.

Right off of 27 so it is super easy to get to. House is on a nice private street with beach access. We walked to the beach several times a day to let the kids play and the dogs run wild. It was beautiful. House is exactly as described and Roger and Amy were great at responding. Quiet neighborhood. Only about 5 minutes outside of Southampton town.

We absolutely loved our quick getaway from the city at Kate’s lovely home. It is hard to articulate in words just how beautiful of a home and location this was. It was truly magical. We were very comfortable as a family traveling with young children. Despite the weather being a bit chilly, we had a wonderful time soaking the views and discovering “treasures” by the water. We cannot wait to come back again soon.

The house was just as pictured. Extremely clean and on a peaceful residential street in a convenient location to explore the surrounding towns. Ana was also very responsive!

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!

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.

We had a wonderful stay at George’s. The unit is exactly as described, don’t be deterred by the adherence to the house, it’s completely private. It’s at a great location for north fork explorations and the amount of towels was outstanding!

I would highly recommend Melissa's place in Jamesport. It was a great location with room to enjoy with some family members including children. It was perfect with some toys and a big outdoor area (and a private beach!) for us all to spend some time together while visiting family in the area. Melissa was accommodating and clear in her directions and gave us a warm welcome with a greeting basket, information about the area and coffee! The location is lovely and everything about the house was fun and comfortable. Thanks!

Incredible place to stay as a solo traveler. Clean, organized and efficient space with everything you could possibly need on site ! Amazing host with such knowledgeable recommendations for the surrounding area. Would absolutely stay here again & could not recommend more.

We had an amazing stay and Ingrid was a wonderful host who was extremely attentive. Would recommend and stay again!