Waterfront holiday rentals in Sag Harbor

Just the getaway for a peaceful autumn weekend with a wonderful water view, lovely grounds and setting. Mark is a very accommodating host and answers any questions quickly. The apartment is well supplied and a short walk to shops. A very relaxing stay!

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.

A wonderful stay in a beautiful location!

Fantastic location! We were literally a two minute walk from the beach. The studio apartment was as advertised and we would stay there again. We highly recommend!

Location was convenient, place matched description and host was friendly and reachable. Would stay here again!

My stay was exactly perfect. Comfortable and relaxing. Lovely area and close to all my activities. Would return for sure.

This apartment is the most perfect space for a getaway. The photos dont do it justice, I was shocked at how big the space was. Right in the heart of the town I could not have asked for anything better. Lucharitos crew downstairs although not affiliated was nothing but friendly and considerate of our stay. I will be back for sure!

Loved Samy’s corner unit, which gave us a bit more privacy and quiet than other parts of the property. The studio was as described, with great light and well-cleaned prior to our arrival. Enjoyed use of the tennis courts every day. Only minor disappointment was that we were not yet allowed to use the pool, which we were told would be ready by Memorial Day (we were there one week prior). Still, a worthwhile stay and I’d come back and recommend it to others.

We had a fabulous stay at this adorable cottage. It had everything we needed and more. Great spaces indoors and out to hang out, walkable to one of our favorite wineries, other wineries & restaurants close by. Appreciated having a tandem kayak to use & explore Goose Creek. Enjoyed watching birds, including Baltimore oriole parents in a nest in the backyard. Would return again. Thank you!

We had a wonderful stay at Harbor House. The view of Napeague Harbor is gorgeous and the sunsets are just next level spectacular. The kitchen is well equipped for cooking in and the furnishings are very comfortable. The location is great halfway between Amagansett and Montaik. We have rented so many homes over the years, but Rod’s house is by far in the most gorgeous setting. We cannot wait to return.

I had a fantastic stay! The property was exactly as described—clean, comfortable, and located in a great neighborhood. Check-in was smooth, and the host was communicative and welcoming throughout my stay. The space had everything I needed, from thoughtful touches to all the essentials. I’d absolutely stay here again and highly recommend it to anyone visiting the area. Thank you for a great experience!

My family had a wonderful time at Robert’s home. The house was clean and cozy and the view of the water was peaceful. He was super communicative and friendly and check in/out was a breeze. The house is in a great area and super close to East Hampton, Amagansett, and Montauk. Highly recommend!

We were very pleased with AJ’s place. We are 2 friends that came to cycle and explore. Location was good. Nice to each have a king bed. Can walk to beach.

We had an unforgettable family Christmas at this wonderful home! It was spacious, beautifully decorated, and had a cozy, welcoming atmosphere perfect for the holidays. The living area was ideal for gathering and the well-equipped kitchen made preparing Christmas dinner a breeze. The large dining table comfortably fit our entire family. The bedrooms were cozy and comfortable, ensuring everyone had a great night’s sleep, and the outdoor space was perfect. The peaceful location provided a relaxing retreat while still being close to local shops and activities. The hosts were fantastic—communication was clear, and they went above and beyond to make us feel at home. We couldn’t have asked for a better place to celebrate together. Highly recommend!

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

Great stay! Very nice and accommodating host. I loved the fenced in yard and so did my toddler/dogs. The place is actually better then the photos. Will happily return in the future.

Stay was great and the place was very clean

We stayed here with our infant daughter and my parents and it was the perfect space for us! Thomas was very thorough and communicative and the views from his place were spectacular! Also very easy and to take the short drive to town to grab a bite to eat and sight see. Would definitely look to stay here again if in the area.

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!

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!

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!

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!