Holiday rentals with outdoor seating in Cutchogue

Staying at Amy's place was perfect for my friends and I while we're out on the North Fork for a wedding. Amy was very responsive with any questions we had. We were all very comfortable in the main living area as well as our bedrooms. The house was conveniently located to the wedding venue and my friends were also very happy that it was located near some pickleball courts. Thank you Amy for a wonderful stay.

We had a great stay. The house was warm and inviting. Very peaceful and quiet. Plenty of room for the family. Very easy to get to and very close to downtown. I would highly recommend!!! Steve was very friendly and responsive to all our needs!

An amazing home that was the perfect spot to host my crew that was shooting a film nearby. Hattie really went above and beyond to accommodate us - super responsive, considerate and the place was had such a relaxing vibe by the water :) Can’t recommend this home highly enough!!!!

We had a wonderful stay at Ellen’s place. The house was beautiful and well appointed with anything you could need - it made us feel right at home. The backyard was gorgeous and relaxing. We were traveling with a toddler and Ellen made sure we had everything you could need for a child. The house had lots of room and was extremely comfortable. The neighborhood was beautiful and it was a quick drive to plenty of things to do. We could not have been happier with our stay!

Our hosts were amazing. They responded quickly. They were very welcoming to us and provided easy-to-follow instructions. The location was great and the house was lovely. I would definitely stay here again.

our group found this place when planning a trip to Montauk, and while we did make it to Montauk as well, Greenport was also a pleasant surprise. Great community and quaint town! The place was amazing too! clean rooms, very cozy. And a complimentary wine bottle! Highly recommend!

Perfect location. Great neighbors. Nice backyard. Close to Macary vineyards

My two girlfriends and I stayed at Marianne’s house for a weekend escape, and it was absolutely perfect! The house was clean, cozy, and easy to find. I especially loved the peaceful morning walks to the nearby coffee shop. Marianne was incredibly responsive and offered great recommendations for things to do in the area. Thank you so much, Marianne – we had a wonderful time!

⭐️⭐️⭐️⭐️⭐️ Clean, Comfortable, and Thoughtfully Prepared! We had a great stay! The place was spotless, quiet, and exactly what we needed for a few nights of good sleep and hot showers. It was clear that the host put thought into making guests feel welcome—there was a mini chocolate bar and a bottle of water waiting for each of us when we arrived, which was such a kind touch after a long day of travel. Check-in was smooth, the bed was comfortable, and everything worked perfectly. While we didn’t spend much time there beyond resting, it was the perfect place to recharge. Highly recommend for anyone looking for a clean, convenient, and cozy spot!

We had a great weekend at Nicholas’s place. It was very peaceful in the woods, and we enjoyed using the record player and looking through the books spread throughout the studio. Nicholas was very responsive when I texted with questions and we used his provided recommendations to find breakfast and dinner. We’d definitely stay here again!

Claudias place might be my favorite air bnb I have stayed at. She has EVERYTHING you could ever think of! The kitchen is stocked with supplies and coffee, which I really appreciated. It was extremely clean and so cozy and felt like your own little space. It is comfortable, private, and a perfect get away from the city. Great for visiting Hamptons if you have a car! Also love her recommendations. I would come back here again and would recommend it without reserve!

We were a party of 5 women and we had a wonderful stay. The location was great, the unit was spotless and spacious, the kitchen had all the necessities, the towels and linens provided were very nice quality, and Amanda was a wonderful host and very responsive. We were able to check-in early which is always an added bonus. The only thing we would recommend being disclosed is that the train is right behind the location and came through pretty early in the morning and was quite loud. Also worth mentioning in the description would be the amount of stairs to get up to the living area of the home. This was not an issue for us, but could be difficult if you had large suitcases and heavy items to carry up. We would definitely recommend and would stay again.

Jason was a great host. Very responsive to any questions we had while staying on Shelter Island. The location is great - easy walk from the North Ferry and central to great restaurants. Airbnb was exactly as pictured. Would definitely stay again! Thanks again Jason!

Great place , nice people , very commucative, place has everything you need , clean , and felt home , definitely will come back again for great experience

Bob, Dawn, and their dog, Cooper were the greatest hosts! We felt welcomed from the moment we got there until the moment we left. The apartment had everything we needed and more, and the shared spaces outside were very serene. I would highly recommend this Airbnb for for anyone wanting a relaxing getaway. We will be back for sure

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!

John and Cathy are amazing hosts. This was our second consecutive summer stay in their condo and it does not disappoint. The place and the amenities they provide are amazing and they are a wonderful couple who respects your privacy but are there for anything you need. I recommend anyone to stay here and know they would want to return. Thank you John and Cathy for making our second summer with you a fantastic vacation!

Met all of our needs to be close to family in the area for an event. It's very spacious and the beds are comfortable. The spiral staircase was steep and narrow, but we made it work. Thanks for a great overall stay!

We very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here again!

Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.

We had a great time at Julie’s place. Would love to visit again…perhaps in the Fall. Loved the balcony overlooking the Sound. Julie was very responsive to my questions. She got back to me immediately. I would highly recommend Julie’s home!