Holiday rentals with a fireplace in Shelter Island

We had a wonderful weekend. Great place to stay. Would recommend it highly.

Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

We had a wonderful stay in Greenport! The house was comfortable and very well kept. Everything was pristine. The location was great- a few short blocks into town for shops and restaurants. We had an issue with the fire detector sounding and Kim was kind enough to compensate us for the issue. She is a great and responsive host. Would definitely stay here for our next visit!

Went with a bunch of my girlfriends and had such an amazing time! Lisa's home was amazing and we all felt right at home! So happy that it was a common ground where my girlfriends and I were able to gather around and create unforgettable memories.

The house was clean, well-decorated, had all the things we needed, and private, with a long wooded lot leading down to the bay. We women friends were totally comfortable there. When we couldn’t find the entrance to the driveway off the main road, she stayed on the phone & directed us until we found it. Excellent choice!

We had a lovely fall weekend stay at Paul’s place. The house and the water views are just as pictured. Convenient location allowed us a good home base to explore the north fork wine trail and local businesses. We did have one small plumbing issue during our stay however Paul was extremely responsive to ensure it did not affect our stay at all. It was a nice experience having such a responsive host. Overall our friend group had a great time and would return again.

Beautiful home, really well stocked and super comfortable. Warm, clean and lots of amenities. Comfortable beds, good showers, big lovely kitchen. Lots of space. We had a great stay. Thanks :)

We had a wonderful stay with my family! Everything went smoothly from start to finish. The check-in process was easy and communication was clear and prompt. Anisha and Rob are great host, very friendly and responsive. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed for a relaxing stay. The house is spacious. I really appreciated how well the place was maintained. I would definitely stay here again and highly recommend it to anyone visiting Southampton!

Mark was very responsive and answered any questions I had. The apartment was very clean. Neighborhood is cute and quiet. The private beach is an added bonus. Would stay again.

Great little spot. Easy access to the Hamptons but off the main grid so peaceful and quiet. Very nice host!

Brianna was a wonderful host! Our stay there made it an easy engagement weekend for us! She was quick to respond with our questions and let us do a late check out on our last day. Definitely would book with her again!

Upon arriving we were taken with the location, beautiful and ample plantings and attention to detail like a bottle of wine and a variety of snacks to welcome us. The hosts were gracious, warm, gave us privacy, and great tips on where to eat. Cowfish in Hampton Bays is not to be missed. A large and private hot tub, comfortable lounges, and outdoor shower are just some of the amenities. A fire pit with water views was a great spot to unwind at night. The hosts gave us kindling and a lighter, and were very responsive with other asks and recommendations. It’s a great location with ease of access for both the North and South Fork. Would not hesitate to recommend to others.

Really cute and clean place, so happy we stayed here! It was perfect little place for a getaway to relax, even in the winter months. Everything inside was up to date and it had everything we needed. It even looked better in real life than the photos. Highly recommend!

We had a great stay! This was our first time in the Hamptons and the space was welcoming, well located to the beach, and a nice place to chill with a beautiful garden. Check in was smooth and all instructions were clear.

was clean, and perfect space for just 2 people and right in the middle of where we wanted to be!

Wonderful and cozy apartment! We were in town for a wedding and needed a clean and safe space to make home base. This was perfect. Would absolutely stay again!

My family and I had a wonderful stay - very peaceful and quiet. The house is beautifully appointed and well- stocked. The pool is fantastic and was kept quite warm during a chilly Memorial day weekend. Ann Marie (host) is kind and communicative. We'd definitely return!

George was an excellent Air BnB host!!!! His responses were prompt and answered any questions we had. The location was ideal in Greenport as everything was walking distance. We had an amazing time!

Tony’s place was wonderful. Looks just like the pictures and was a great time for our time away. The place was clean and Tony was also very responsive and accommodating. Highly recommend Tony as a host!

We brought our three adult children here to reconnect and explore a new beach town, and this home was the highlight of our trip. It offered the perfect mix of fun and relaxation—truly the most amenities we've ever had at an Airbnb. We enjoyed nightly game competitions in the incredible game room with golf simulation, ping pong, Pac-Man, racing games, and more. The basement had board games and a basketball shootout we loved. The pool, hot jacuzzi, and dinners on the deck made for relaxing, memorable evenings. Ann Marie was kind, responsive, and a joy to work with. Her eye for design made the home feel like something out of a magazine. The beds were super comfortable, and the natural light throughout the home was beautiful. Thank you Ann Marie, for entrusting your incredible home to our family. The memories we have made are priceless and we are very grateful to have had this amazing opportunity! Our only regret was not getting around to do the Karaoke machine-Next time!

My family and I were lucky enough to stay at Jenna’s over Memorial Day Weekend. The house was even better than the pictures, if that’s possible. Very clean, and beautifully presentable. Everything was clean and ready for us, and Jenna had genuinely everything we could have possibly needed. Jenna was extremely communicative even leading up to our stay. Hope to stay again sometime soon!