Cottage holiday rentals in Sag Harbor

I had a wonderful weekend at Andrew’s place in East Hampton. It was gorgeous, perfect location, perfect layout, and such a central location to everything. It was incredibly clean and organized and the backyard was beautiful for relaxing. Andrew was also a terrific host- he left us beverages, was super communicative and flexible and I’m so happy I stayed here. Hopefully I’ll rent again soon!!

beautiful house, great location and very nice and peaceful neighborhood close to the beach and the vineyards the house is very well equipped ! Richard was very nice and even find a little bed for our baby boy ! thanks !

We had a truly wonderful stay at this charming old house. It’s full of character, beautifully maintained, and well-equipped with everything we needed. One of the highlights was the private yard — perfect for enjoying a quiet morning coffee or relaxing under the stars in the evening. The host was exceptionally kind and helpful, always quick to respond and full of thoughtful local recommendations. Thanks to them, we discovered a few amazing winery with surprisingly good wine and a warm, welcoming atmosphere. This was a peaceful and authentic experience — perfect for anyone looking to slow down and enjoy the local charm. Highly recommended!

Wow!! The perfect peaceful getaway that is close to everything!! Tucked away off the road the house is quiet with a beautiful yard. The interior is both stylish and comfortable. The kitchen is extremely well outfitted. Andrew is a great host and an excellent communicator. We only wished we could have stayed longer!! The question isn’t will we come back, it’s simply when!

Manuel (along with Lorena) we exceptional hosts. Always responsive, friendly, accommodating and just a pleasure to deal with. The house is wonderful. Well cared for, charming and a joy to visit. The location was incredible walking distance to both the jitney and the train! The yard was amazing, lush, quiet and beautifully landscaped. The pool and spa were top notch and we will definitely be coming back. Wow

We absolutely loved Michael's cottage. It is a ~15 minute walk from the village and is on a quiet street. The cottage feels like a beach house but is very well appointed and homey. We loved our stay and would absolutely stay here again!

We had a great stay! The house was pristine and the kitchen was very well stocked. The cottage was very close to beaches, restaurants and grocery stores! I would definitely recommend to anyone looking to get away for a beach vacation!

The interior and backyard of this Airbnb are absolutely gorgeous - even prettier in person. The backyard has beautiful landscaping, a lovely fire pit, lots of seating and a large lawn perfect for dogs - it feels luxurious. The interior is expertly designed with peaceful coastal colors, a working fireplace and warm lighting. There is only one bathroom, which could be tight depending on the number of guests, but it was stocked with Aesop products and everything was sparkling clean. Stephen was very communicative and provided some great recommendations, including a quiet and dog friendly beach only a few minutes away. Highly recommend!

This place was cozy and quaint. We were only missing a can opener! You too will like it! I would stay here again

I can’t say enough wonderful things about this spot and Monika. This is our second stay- my husband, toddler, dog and I loved it last summer and came back. The back sliding doors open onto a porch where birds chirp and visit all day. The bright green lawn under towering trees is perfect for playtime or a family picnic. Little touches of thoughtfulness and charm are just everywhere. Monika’s hospitality is unparalleled- snacks and a handwritten note upon arrival, homemade treats throughout our stay, and nearly instant responses. Without being asked, she even sent us a hand-drawn walking route for a dog and baby and directions for getting there. Beaches, playgrounds, town centers, bagels etc are a short drive. The street is busy so wouldn’t go for a nearby walk necessarily but thats pretty standard throughout the Hamptons. For parents of young kids: FYI there isn’t laundry, but truthfully I just packed more- that’s how much we liked it. A laundromat is also nearby tho!

Super peaceful and quiet location. Home is adorable and gets lots of natural light. Proximity to the beach is amazing! Would recommend having a car though as it’s little bit away from town & Main Street. But plenty of Ubers in the area! Overall, I was really satisfied with everything and it fit my needs.

Our stay was enjoyable. Erin’s cottage, both inside and out, was clean and well maintained. The kitchen has a professional stove. I was able to bake a chocolate cornbread and pan fry fresh scallops from Southold Fish Market. The hammock was an unexpected pleasure. I haven’t been in one for many years. Hope to return next year.

This is an amazing location. Beautiful kitchen with all of the amenities. The living area is comfortable and spacious. The whole home feels much larger than it appears in the photos. Would 100% stay here again.

Had a nice stay here with a group of people attending a wedding a short drive away.

Our stay was fantastic from start to finish. The space was exceptionally clean and well-maintained, which made us feel instantly comfortable. Check-in was seamless and clearly communicated, allowing us to settle in quickly without any hassle. The host was incredibly responsive and helpful—always available to answer questions and made sure we had everything we needed throughout our stay. Overall, a smooth and stress-free experience! Definitely will book again in the future!

Greg’s place was exactly as advertised. The accommodations and location were excellent! The outdoor space was very special, perfect for early morning coffee and evening unwinding. Communication with the host was easy, though we didn’t need a thing. The local recommendations he provided were appreciated. We really had a perfect stay! Would definitely return to this location next year.

Our second stay here and we enjoyed coming back to this lovely and functional home. Love having a well stocked kitchen, large laundry, and beautiful bathrooms. Very private and safe area. Bike-able into town, which is a plus. Would return when in the area again. Overall a great experience.

Great base to explore Sag Harbour. Janine was a very proactive host and ensured we had everything we needed during our stay.

I'll start by saying that Benjamin was the most accommodating host that I have ever dealt with since using AirBnB 6 years ago! The home was in pristine condition, and his attention to detail was something you aren't used to when staying in rental homes (we were provided with wamsutta towels!!! IYKYK). I was working in the Hamptons with a few colleagues and our initial rental canceled on us at the very last minute leaving us stranded. I reached out to Benjamin, who was extremely responsive, and he accepted our request. Another colleague suffered the same fate, and needed a place to stay, and Benjamin accommodated. He absolutely did not have to, but went above and beyond! So, thank you Benjamin!! If I had another 1,000 characters, I would talk about the grass, but I guess you'll just have to rent the place for yourself to understand what I mean. I promise you will not be disappointed!

Lovely stay. Short walk to beach, so no parking worries. Great local store right on the corner, a couple of bars/restaurants within walking distance. Kitchen stocked with the basics like dishwasher powder, salt, pepper, oil etc. Nice bbq in the garden. Ideal location for discovering the Hamptons.