Holiday rentals with a fireplace in Shelter Island Heights

The house was so cozy and comfortable and well stocked. I didn't even miss not having a tv. there are games, records to play on the record player, and plenty of kitchen utensils and spices to experiment in the kitchen. I enjoyed relaxing by the fireplace and walking in the neighborhood. You will need a car to be able to access restaurants and shopping, but it was a short drive. It was exactly what I was hoping for and would return again.

I have never stayed in an Airbnb before. Bc I like a clean pristine place and prefer a hotel. I am converted after our stay. This house is so amazing pristine and clean. We enjoyed the fabulous design and comforts of home while being there for 5 night for our son’s wedding. I would stay at the house again in a heart beat. And to our surprise it was way bigger than it looks in photos. Thank you Ashley for having us.

House was perfect for our quick And easy family get away. Would certainly Stay again and recommend

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.

Had an amazing time! The location is great. On a very quiet road and close to the water, incredibly peaceful The house is great, everything you could want and also everything is very simple to figure out. So you feel right at home instantly The layout is great with indoor/outdoor living being seamless! The pool was lovely and warm, sauna was great and hot tub perfect! Couldn’t ask for any better, Brilliant attention to detail and a lot of effort to make it a great place for anyone to stay! Benjamin was lovely to deal with, will definitely stay again!

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.

Benjamins place was a wonderful stay for our family. Coming from the City it was amazing to have so much grass with peace and quiet. It is a short walk to the Main Street and Sag Harbor downtown. We had planned to go out and enjoy some activities during the couple of days we stayed but instead found the place so relaxing we spent most of it in the home. The separate house was nice for a master bedroom and quiet. We would highly recommend this house to anyone wanting to have a relaxing and quiet vacation in the Hamptons near Sag Harbor. Hope to be back again!

So clean, like really, really clean. Short walk to small private beach. 1 mile from 2 different big beaches. Southport Seafood is great. Lots of wineries. Greenport has some excellent restaurants and shops.

We had an absolutely wonderful stay at Barbara’s beautiful home! From the moment we arrived, everything was spotless, well-maintained, and exactly as described. The house is full of charm and character, with thoughtful touches throughout that made it feel like a true home away from home. The location was perfect—peaceful and quiet, yet close enough to everything we wanted to explore. We especially loved the cozy fireplace, comfortable beds, and well-equipped kitchen. Barbara & Patty were incredibly responsive and helpful and made sure we had everything we needed for a comfortable stay. This was our 3rd time staying here and we highly recommend this place to anyone looking for a relaxing, beautiful getaway. We’d definitely love to return in the future!

very good place to stay, spacious, felt just like home

Can’t wait yo go back Felt at home Excellent!! By far best Airbnb I’ve ever stayed at

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 :)

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!

Beautiful fall stay at Jo’s! Loved the space, amenities, and especially all the directions and recommendations for the area. Will definitely come back again if we are in the area.

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.

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!

Our family had a very enjoyable stay! The home and surroundings were beautiful, everything was extremely clean and organized, our host was wonderful! We absolutely loved the tea ceremony! It was very educational! We will definitely stay here again when we return to New Haven!

Our stay at this stunning lake house was nothing short of amazing. The moment we arrived, we were welcomed by a breathtaking panoramic view of the lake that instantly set the tone for a peaceful and relaxing getaway. The house is incredibly spacious, with a well-designed open layout and large windows that flood the space with natural light. Every room felt bright, airy, and inviting. Cleanliness was top-notch—the entire place was spotless and clearly very well cared for. We loved how quiet and serene the surroundings were; it felt like our own private retreat away from the noise and rush of everyday life. Mornings spent sipping coffee on the deck and kayaking over the water by the backyard lake were highlights of our trip. Whether you're looking to unwind, connect with nature, or simply enjoy some peace and quiet in a beautiful setting, this lake house is the perfect place. We’re already dreaming of our next visit and would recommend it without hesitation.

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 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 !

Dove Haven is truly a special spot that shows that someone (Patty) cares about it a lot. The house is very well stocked and we never lacked for anything. And the collection of available umbrellas was greatly appreciated (yes, a bit of rain). Spacious hot tub (accommodates 8, nicely) is well-located on adjacent deck with beautiful view of spectacular garden. Rare to find a place where each of the five bedrooms, (with en suite or nearby bathroom), would be a master bedroom in a typical Airbnb. The master bedroom lives up to the billing with a monstrous bathroom including an inviting tub and a private porch. Public tennis courts and public pickleball courts nearby (less than a mile down West Rock Ave) were a treat. As was brunch at Bella’s Cafe (highlighted in Patty’s online notebook). Just plain terrific from beginning to end.

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