Holiday rentals with a fireplace in Shelter Island

Anne Marie’s cottage was exactly as described right along w/the peaceful surroundings, lovely views of the water and close proximity to beach and town. She gave us recommendations for local gems, and we thoroughly enjoyed our time. We will certainly try to get back again. Cheers to the host 🥂

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!

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!

Lovely setting in the woods. We loved the layout, including many windows with beautiful views. Quiet neighborhood that is very walkable. Seeing baby deer in the spring was an unexpected bonus. Spacious bedrooms with extremely comfy beds. Host responded quickly when we had an issue. The private beach is a fantastic feature and easy to access. Check in and check out were super easy.

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!

We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

Jaime and Wilson are amazing hosts, sweet and attentive. Their place is tastefully decorated and they made small tweaks to the house for my partner and I and left a card for us. They also leave umbrellas for their guests in case it rains, which happened and we got to use them. Their attention to small details, in addition to how clean and comfortable the place was, made the stay super memorable. 🩵

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!

lovely environment, beautifully designed garden apartment

This place was great. Clean and modern and everything you need. One of the, if not the, best AirBNB I’ve ever stayed in. The pictures don’t do it justice. The place was exactly as listed. However, business travelers note, there is not a full sized/comfortable work-station. But Patty, who is very responsive, said she is working on it. I would definitely stay again. Seriously, you will get a lot less for a lot more at other places. If you need to be in New Haven, and you only need a studio, this is the place.

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

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!

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.

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

Spacious and beautifully decorated this house was the perfect spot for our girls weekend. They were 10 of us and the house had everything we needed for a fun weekend. Highly recommend.

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!