Holiday rentals in Sag Harbor

I recently had the pleasure of staying at a charming Airbnb in Sherley. and it truly exceeded my expectations! From the moment I arrived. The check-in process was seamless. The host provided clear instructions. The apartment was impeccably clean, beautifully decorated, and well-equipped with everything I need. The location could not have been better! Situated within walking distance to local attractions, restaurants, and public transportation, I found it easy to explore.

Had a great weekend at the cottage! Meredith was so great letting us check in early and was super helpful and responsive. The cottage is gorgeous and has everything you need. Loved it! Thank you!

We had another great stay at Claudia's place! This was our third visit to this location, and likely not our last. Thank you!!

We had a wonderful weekend stay at Eileen's beautiful waterfront home. The view from the living room and primary bedroom of the water was so peaceful. The kitchen was well appointed and the cozy living room made for a wonderful family gathering spot when we weren't dining out at the fabulous nearby restaurants, visiting wineries, or viewing local scenery. Eileen was incredibly responsive to small questions we had. We would definitely book again!!

Earl, was great to work with. We were only there for few hours. However I would recommend highly and will look to stay here again should work bring me back out that way.

We needed a dog-friendly ranch style to home with three bedrooms and two bedrooms close to Sayville, where we would be celebrating Thanksgiving. I was lucky enough to find this rental which was clean, comfortable and ideal for our two-night stay. Adam was attentive and easily accessible via text. I would highly recommend this lovely home.

Our family spent a great weekend here. There was plenty of rooms for everyone to have their own, and everything was clean, cozy, and comfortable. The home was exactly as shown in the pictures and everything we could have needed was there. The hot tub was lovely both nights, and the pool area looks pretty though was not yet opened for the season. This is a perfect spot to bring your family, to relax, and enjoy all that the Hamptons, and Hampton Bays has to offer. We hope to return soon!

I spent the weekend at Eric's house with my parents and it was absolutely perfect. Such a bright, comfortable house in an incredibly convenient location. ~5 minute drive to Sag Harbor town, ~15 minute drive to Sagg Main beach, and ~10 minute drive to Wolffer Estate. We experienced a few issues upon check in (had some trouble working with the electronic door lock, no toilet paper), but Eric personally called me and made it his business to resolve it. He really demonstrated being a great host and making sure that we had no issues. I would definitely stay at Eric's property again, it truly felt like a home away from home.