Beach house vacation rentals in Greenport

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!

had an amazing time staying at Jessica's house. the place is close to everything, very convenient. Jessica is very quick to respond and flexible with check in and check out. Will definitely come back

Beautiful home, very clean, spacious and comfortable to stay with the family. We used the grill on multiple occasions and it was easy to use. The fire pitt was also enjoyable. The kitchen was well stocked, would bring own source of caffeine if you’re picky with your coffee though. Stephen, the host was very responsive and easy to reach when asked questions. The one thing I would recommend is to check in with the host if the pool is available to use prior to booking. Overall a great experience, would stay with them again.

Maher’s home is so elegant and mid —such great taste. He was such a kind host and so very easy to communicate with. The pool was lovely and the garden and back so pretty. We had a brilliant time! Thank you.

An amazing stay overall. It was comfortable for 6 adults. Spencer was extremely helpful throughout our stay — I had lots of questions and Spencer was quickly responsive. The house itself is beautiful and has that eastern Long Island charm. The backyard had lots of space and is well maintained alongside the pool. We also enjoyed a sunset evening at the beach which is just a few steps away. It was a wonderful weekend and I am certainly looking forward to staying here in the future!

The house has an incredible location, walkable to town but quiet, with a large private backyard with a pool. The house is nicely decorated and the beds are very comfortable. It was cold and rainy during our stay in late May, but the heating system worked very well. The kitchen is well stocked if you want to cook dinner, but it would be helpful to have a colander to rinse vegetables and berries. Overall, a wonderful place to stay!

Beautiful house, even nicer than the photos. Great location to tour local wineries and close to the greenport’s Main Street! The house is stocked with plenty of cooking utensils and has whatever you might need. Would definitely consider coming back in the summer to enjoy the backyard when the pool is open!

Benjamins place was a wonderful stay for our family. Coming from the City it was amazing to have so much grass with peace and quiet. It is a short walk to the Main Street and Sag Harbor downtown. We had planned to go out and enjoy some activities during the couple of days we stayed but instead found the place so relaxing we spent most of it in the home. The separate house was nice for a master bedroom and quiet. We would highly recommend this house to anyone wanting to have a relaxing and quiet vacation in the Hamptons near Sag Harbor. Hope to be back again!

Nautical Cottage was a very comfortable house with a great outside area. We loved the fire area and the BBQ plus good comfortable outside furniture. Good location to explore the entire Hamptons area. Loved Cowfish and Rumba for delicious food. Bedrooms comfortable and sitting/dining/ kitchen a good size for relaxing and playing games (a great selection). Coffee machine fab! The perfect spot for a wonderful family getaway! Thank you!

This was the most beautiful house in a private area in Wading River. It offers peace and tranquility and lives up to its name of Zen Retreat. It was exactly what we were seeking. Conveniently located near parks, farms and wineries I would definitely go back to Brian’s AirBNB. He was an excellent host and very responsive to our needs. Thank you Brian.

Jason was great, very responsive and helpful with my mom. Dog friendly, and there are pet pigs and chickens, too!

John’s cottage is situated on a beautiful piece of land with a substantial water view and a lovely place to walk. The cottage was comfortable with lots of amenities and well cared for. Driving around the property one late afternoon, we came upon four large deer who arose one by one, glanced at us and went on their way. Very nice. John was a personable, friendly and helpful host. We’d definitely stay again.

Our stay was exceptional and the views truly breathtaking!!! The home was pristine and geared to spending quality time together as a family, which we appreciated greatly. We traveled with our son and his family. The 4yr old twins, loved spending time outdoors and in the private beach area. They even had a large container available to them filled with an assortment of items which they used to build sand castles with their parents. Communication with our host was outstanding. It was evident they went through great care to make their home welcoming. Nothing was needed, but we knew they were but a call away. There was plenty of information in a binder available to guests with an array of eateries. Being in the medical field cleanliness is key… and this definitely was vacation ready. So make your plans, pack your bags. It won’t disappoint.

great stay in great location in sag harbor. we had a toddler and a senior with our family and the space was pitch perfect for all of us. a very special place and we’re so glad we picked molly’s place. hope to stay here again soon!

The house was clean, well-decorated, had all the things we needed, and private, with a long wooded lot leading down to the bay. We women friends were totally comfortable there. When we couldn’t find the entrance to the driveway off the main road, she stayed on the phone & directed us until we found it. Excellent choice!

Really enjoyed our stay in Hampton Bays, Brian’s house is exactly as described. Spotlessly clean, very well equipped and perfectly located on the beach. We’d highly recommend the property to anyone, particularly families with young children. We ate next door at Rumba twice, Cowshed and Edgewater. All excellent and all walkable.

Had an excellent stay at Eileen’s place. The house was extremely clean and perfect size for a couple. Beautiful view and surroundings. Only wish I had more time to explore the area. Would definitely stay here again if I return.

Fantastic cute spot in Old Saybrook. Key things for future guests to know - there is no A/C in the winter months so the air can get a bit stale / stuffy in the house. Plus there is no washing machine / dryer in the house, so defo bring enough clothes!

This is a very clean and comfortable house with good quality linen and towels. There is minimal clutter and the place is well furnished with everything you need in the kitchen. The house gives off very good vibes. The view from the French windows across the deck to the little bay is exquisite. All in all, highly recommended.

My family and I had such a wonderful stay at this house. The house was immaculate and well stocked for our stay. Matthew and Celia are great hosts. We really appreciated the basket of snacks and dog cookies that were left for us and our fur babies (Thank you!). They truly thought of everything and it felt like “home” the entire time we were there. The views from the back deck are truly spectacular. We spent many hours sitting in the sunroom and out on the deck enjoying the sights. My pups enjoyed daily walks at the sea wall park that was steps from the house. I can’t say enough great things about our stay. Thanks to our hosts for sharing their beautiful home with me and my family.

Peace & tranquility! If you’re looking for some privacy with a view, I highly recommend!

Loved our girls’ getaway on the North Fork! Mae’s house is the perfect spot with a quick walk to the beach and gorgeous views right from her backyard - even close drives to beautiful Southold, Mattituck, and Greenport. I will absolutely stay again!

Spent to my birthday here with my husband, dogs and toddler. Had my gender reveal birthday cake, outback under the sunset. Truly magical.✨ The backyard was ideal. Was able to tie the dogs to the deck with a 20 foot leash. It kept them contained to the backyard & away from beach goers on foot and other dogs. The dunes kept the backyard private you’re not staring at your neighbors. Felt so secluded. I also have some mobility issues and you couldn’t ask for an easier way to enjoy the beach & get your toes in the sand. The house & deck are spacious and easy to navigate with a walker. Was able to add extra days to our stay. Would 100% stay here again.

We have had several family vacations on the North Shore now, but this was beyond our expectations. Pretty much a private beach on LI Sound in your backyard. Amazing layout with a wrap around deck with three daybeds for lounging outside among the tall hardwood trees and listening to the waves. Hammocks, hot tub and sauna below with a private gym and knocked out theater setup for streaming movies. There were 5 adults and two three year olds on this trip so the 3 full baths were great. The house felt like home for 7 great days and nights. Rainy days were filled with train museums, an aquarium and butterfly gardens and a fabulous library. And the North Atlantic waves are a 25 minute drive. Oh , and everyone said the beds were super comfortable.