Holiday rentals with a fireplace in Southold

We had an amazing stay at Michael’s Airbnb this past weekend! The space was exactly as described—clean, cozy, and well-equipped with everything we needed. Michael was a fantastic host: super responsive, thoughtful, and made us feel completely at home. The location was perfect for a relaxing getaway, and the setting was even more beautiful in person. Would absolutely stay here again—thank you for a wonderful experience, Michael!

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

This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!

Wonderful stay - perfect house. Walk to local attractions, clean, comfortable and cute. Exactly what we needed. Would love to come back. Thank you!! 🙏

Jennifer’s place is great and in an amazing location. We loved it and it was perfect for the weekend. Very clean, spacious and great backyard.

Kathy was an amazing host. She was communication and helpful with everything we needed or asked for. Her place was absolutely incredible. Would definitely stay again!

We had a fantastic stay here. House was beautifully decorated, spacious, and had everything we needed. Host was great, responsive, and provided easy instructions to everything in the house. Will be staying again.

Alexis welcomed us at her gorgeous Airbnb. The place is very well though and practical. It is soothing and relaxing. I would recommend this opportunity anytime, and looking forward to come back soon! Excellent experience for a reasonable price!

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. 🩵

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!

Paris is a wonderful host. His property and cottage is a perfect retreat for two. Charming accommodations with a beautiful view and an easy walk to town. We’ll be back soon! Angelo C.

The home is in a great location with very quick and easy access to downtown. It is a beautiful place to stay; Wilson and Jaime are very welcoming and make sure everything is taken care of in order to provide a wonderful stay. Definitely 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!

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 :)

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!

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.

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!

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 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!

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!