Holiday rentals with a fireplace in Shelter Island

Ashley’s location was amazing and the entire layout was efficient. The automated blinds and Sonos wireless surround system were amazing highlights of the property. The hot tub worked flawlessly and the amenities were well stocked. Ashley’s house is well stocked to host a private dinner party for guests with the large prep sink and counter areas. The newly renovated kitchen cabinets all had slow closure mechanisms and the dual oven microwave was a nice touch. The dual shower head in the downstairs bathroom was a useful amenity as well.

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!

An ideal location in Southampton, Lori’s house is clean, cozy and peaceful; we thoroughly enjoyed spending our New Years there!

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!

Loved this spot! Clean, cozy, and perfect walkable distance to all the great restaurants. Super friendly and responsive host!!! Made it super easy and felt right at home.

We have stayed at Giuseppe’s home many times. The house is in a location central to many great restaurants, shopping, & other things to do. His home is immaculate—so clean and has all the essentials you will need for your stay. The heated pool and backyard is ideal to get some sun and just chill. Giuseppe always responds promptly to messages. If you are looking to stay in the Hamptons, don’t hesitate to stay at Giuseppe’s home! Looking forward to our next stay already

Britta is lovely. Her home and surroundings are truly nothing short of magic. Her taste is impeccable. The home is even more beautiful than the pictures and is actually quite large while still maintaining coziness. We hope to return regularly. Thank you, Britta. We will always remember this weekend.

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.

A wonderful stay in a beautiful location!

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.

Peter was extremely responsive and helpful. Helped with all requests and accommodations. Would recommend and book again. 10/10

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!

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!

I recently had the pleasure of staying at a truly exceptional home that exceeded all my expectations. The house was clean and well-kept. It felt like stepping into a brand new space. The backyard is a standout feature, offering a fantastic oasis for families. The pool is perfect for kids, Additionally, there's a well-equipped playground that kept the little ones entertained, along with a variety of toys that made it feel like a true home away from home. The office space was a welcomed surprise. It features a comfortable desk and ample natural light Overall, this house is a gem, perfectly blending comfort, fun, and functionality. I highly recommend it to anyone looking . Can’t wait to come back ! Thank you !

It was perfect for the holidays it made everything better for me and my family

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!

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!

We had such a wonderful stay at Ann Marie’s Airbnb! From the moment we booked, she was incredibly kind and responsive, making everything so easy and welcoming. The house itself was spotless, beautifully maintained, and had every amenity we could possibly need — it truly felt like a home away from home. The location was perfect — close enough to town that everything was easily accessible, but just far enough out that we avoided all of the typical Hamptons traffic. We even walked around the neighborhood every morning! We couldn’t have asked for a better balance of convenience and tranquility. Highly recommend this stay, as someone who frequents the hamptons — we’d come back in a heartbeat!