Cottage vacation rentals in Greenport

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 !

Ivana and John are the most wonderful hosts! This was truly like staying at a family cottage and everything was just beautiful. John greeted us upon arrival and even had a bottle of wine for my husbands birthday! We loved staying here from the city because it was only a little over a hour to arrive and less than a hour to South Hampton where we had dinner. Also the little town is so so cute and we were able to walk over so quickly! We can’t wait to stay here again. Thank you again Ivana and John!

Great communication with host, beach within walking distance was so nice, overall good spot within 30 mins of mystic aquarium and Foxwoods casino

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!

Tabitha's place was perfect for our group stay. Right in the middle of town and perfect for what we needed for the week!

Our stay at Andrew’s cottage was delightful. Nestled in a prime location, the cottage provided the perfect base to experience the diverse beauty and charm of the Hamptons including the renowned North Fork wineries. The peaceful & serene surroundings offered relaxation after busy days, while the outdoor space was perfect for morning coffee or evening drinks. The cozy bedrooms and comfortable beds ensured quality rest, and the kitchen was well-equipped with everything we needed. Minor issues were quickly resolved, showing Andrew’s dedication to providing top-notch guest experience. This stay created cherished memories, and we highly recommend the cottage for anyone seeking a delightful getaway in the Hamptons. We can’t wait to return & enjoy all this special place as to offer!

Quiet, peaceful. Pictures do not do this place justice. Perfect place for 2 couples or 2 couples and kids. Set up was great.

Stayed at Danielle’s home with a few of my girlfriends for a chill weekend away from home. Lovely and cozy space and beautiful neighborhood where we were able to catch some sunsets at the beach down the road. Perfect size for me and my friends. Hoping to make this a yearly tradition :)

Very comfortable and clean cottage! Love the history and pristine condition of the vintage kitchen and bathroom. Very responsive host. Thanks!!

Jeanne's place was perfect for my trip to Guilford. Excellent location, close to the Green and to the water, quiet, peaceful. The house had everything I needed and more, Jeanne was super responsive and kind, and the bed was comfortable.

Great weekend on the North Shore of LI. My husband and I came for a wedding in the area and we were so happy we stayed at the cottage. The beach is so close we walked over and everything we needed was right there. We even enjoyed some wine and cheese on the outside porch before we walked to dinner at Legends. Would definitely recommend and hope we can get back to the cottage 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!

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.

Angela was a great host and very accommodating after an unfortunate personal event we encountered just after arriving. The cottage was very comfortable and immaculately clean. Love the keyless entry. Neighborhood is quiet and we felt extremely safe. Deer pass through the yard throughout the day and what's more beautiful than that!!! We absolutely recommend Angela as a host and would not hesitate to book again in the future.

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

Myshkin’s place made for a nice 3-night getaway. It is private, clean, and quiet. About 10 min drive from each Sag and EH which made for easy access to both. The private beach is a 5 min walk and was great even in the offseason. In short, it makes for a great escape in a quiet part of the Hamptons.

Susan is a fantastic host and the cottage is a lovely place to stay. Steps from the beach and a quick drive into town plus pool access right out your door. Susan was great to interact with. We definitely plan to come back.

Amazing host, amazing house beautiful view excellent location perfect getaway!

Michelle was extremely responsive and flexible with us throughout the process. The stay was perfect for our five person group and we all loved the decorations and interior design. Plenty of towels and a good number of blankets. Pull out couch bed was comfortable. The fire pit was functional and very pretty. Kitchen had a coffee, plates, cups, utensils. There was also a vacuum which was very helpful with the inevitable sand that would come in after a beach trip. We felt we had everything needed for a fun and enjoyable stay! Neighbors were friendly as well and the beach was nice and private.

Peter's beach house was the perfect extended weekend getaway with our family. It was the first time we took a family vacation with our small children and teenager. The little kids loved the top bunk in their room and my teenager loved having a room to herself. The kitchen was perfect for our needs, the kids loved the sunroom and the living room was great with the tv for nighttime relaxing. The walk to the beach was the perfect length and the beach was clean and open. We loved every moment at the beach house and are hoping to return next year.

We had a great experience staying at Melissa’s cottage and would happily recommend it to anyone else! We were in town from Florida visiting family in Rocky Point for Christmas and chose Melissa’s property as our place to stay. Melissa was very communicative, check in was super easy and we felt right at home on her property. Would definitely consider staying here again. Thanks Melissa!

Spent the weekend here for my husband’s birthday with our kids. They loved the big private beach. Almost no one else was on it. We needed an air mattress for our daughter and they quickly brought one over. The place was STOCKED with everything you could need!