Holiday rentals with a fireplace in Shelter Island

I was traveling to Amagansett for work and stumbled upon Elise's place. Elise was super responsive (even though she was across the other side of the world), very accommodating and ensure my check-in and check-out was seamless. Highly reccomend. Note it is in a very quiet / remote part of Amagansett but only 5-10 min drive to shops, etc.

This beautiful home did not disappoint! There was lots of space for our group of 7 ladies to eat meals together, sit outside for coffee, play games and sleep in the comfortable beds. Lots of amenities including utensils, cookware, plates, glasses, towels, etc. We walked to beach and it was a quick drive to town. We are already planning our next year’s visit! Thanks for being super responsive Adam!

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 rented Nick’s place for a long overdue weekend of friends getting together from different bits of the world. The house is conveniently 1hr45mins from JFK and an easy drive from the city. The house was very spacious and perfect for a long weekend. Nick was very responsive and truly went above and beyond trying to get the pool working off season for us. The property is about a 10min car ride from the Southampton Main Street with loads of good restaurants. We also really enjoyed the sauna. Thank you Nick!

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!

Ashley’s house is the perfect get away. I booked this house for my family to stay for my wedding weekend. My mom had never stayed in an Airbnb before and I’ve never seen her so happy and relaxed. She truly enjoyed her first Airbnb experience at Ashley’s place. It was exactly as described and the view is beautiful. Ashley was very responsive and made sure to answer any questions I had.

We had a lovely weekend at Rachel's cozy abode! The home was perfect for a few of us working remotely for the week. We were able to enjoy the peaceful backyard & pool and the house was stocked with all the kitchen essentials we needed to cook a few meals at home. The location of the house is also great--we enjoyed the quick drives to nearby beaches and our dinner outings. Rachel was communicative, kind, and responsive. We hope to be back for another getaway in the near future!

Ben is a super host. His home is absolutely beautiful and well managed. His thoughtful recommendations and well timed check ins and reminders were the height of polished professionalism. We felt right at home, down to the bins of toys in the living room that our toddler and baby played with every day.

A wonderful stay in a beautiful location!

Ronnie & Brian’s place is awesome! Tons of space and very well maintained. Great location. They are very responsive and we will definitely be back!

This was my second time staying in Paris' cottage and it was just as charming and lovely as the first time. The cottage is set back from the road, nestled in a charming neighborhood. It's a very comfortable, quiet and peaceful place with a beautiful view and privacy. The center of Sag Harbor - with shops, restaurants and a sweet movie theater - are all walking distance from the cottage! Thank you for another great stay, Paris!

Joanne was a great host! The Airbnb was clean and exactly as displayed in the description. I would definitely come back to visit - the neighborhood was also beautiful and very peaceful.

Selestria was super kind & supportive! She made us feel welcomed and made herself available for calls if needed. The home was clean and nice looking :)

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!

The house was wonderful - homey, comfortable, cozy, and great decor. The wood stove was awesome for the chilly evening. Kitchen very well equipped and up-to-date. Nice restaurants well within walking distance and a short drive to Montauk downtown. Only comment would be small bathroom, but it served us well.

I look forward to stay Lismary place on my next trip. Great location, very clean and well decorated. I feel like I am at home.

This home was beautiful and exactly as described. The hostess was wonderful and very responsive. The location in east hampton in a quiet and peaceful street was close to all our favorite restaurants, shops and beaches. The hot tub was so great to have in the cold and rainy days. The home is chic, comfortable and clean. We loved it and recommend it.

We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

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!

We hosted a family gathering and this house was absolutely perfect. It was stunning! Lots of curiosities in the house. Had a grand piano that we could use for entertainment. The place was clean, pool was well situated, beautiful balcony for meeting up with friends and family. We booked it for Yale graduation weekend and no hotel in the area could match the experience we had.

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!