Cottage holiday rentals in Shelter Island Heights

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!!

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!

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!

We had a great time at Great Gull’s! The location was perfect, walkable to all of the shops and restaurants. We even walked to the Seaport. Having the kayaks there was awesome, we enjoyed our first experience kayaking as a family! We loved walking to ice cream and bringing it back to sit on the patio and watch the bridge go up and down. I would highly recommend this place! And the owner, Gerard, was extremely attentive!

We enjoyed our stay at the cottage. I had reached out to Lisa numerous different times and she was very understanding and quickly responsive. The home itself was clean, walking distance from the beach, and I loved it was nice and cool inside from the AC.

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!

Perfect getaway close to the city. Beach is beautiful! Brooke has the place stocked with everything you'd need. Will definitely be booking again!

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.

Cabin & location was exactly as described. Pristine lawn, overlooking the ocean and pool. Loved that the cabins were super clean and pet friendly because we spent all morning (until 10am) on the beach with our standard poodles! Just screen your pets for the tiny (freckle size) ticks. We later learned that Montauk had a high rate of lymes. Beach access was within walking distance (less than 5 mins), but restaurants were not within walking distance. Definitely recommend bringing bicycles because it’s a short 2mile distance to the heart of town and they have bike parking almost everywhere we went. Would definitely recommend Ron’s cabins to our friends and family because it truly was a gem of a find!!

Wonderful place to get away from the busy life. We found it relaxing and a convenient 20 min drive to the academy We will definitely book again!

Erin was incredible and extremely helpful during our stay. Responsive and kind, highly recommend a stay here! Thank Erin!

Absolutely perfect for us. Cottage was very comfortable, super clean, and beautiful. Loved the location. I had read about the bathroom through the back door and the low tide beach so no surprises and everything was just as pictured. Would stay here again if we get the chance! It’s a little gem.

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.

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

Wonderful bay side cottage! Stayed here for a long weekend with my husband and in laws. It’s a great location!! Water views, walkable cute neighborhood, and 20 mins from some of the bigger towns (Jamesport & Greenport) Place was clean and a fully stocked kitchen made it easy to stay in and grill out.

Our group loved our stay with Jeff! His place was incredible, clean, and spacious!! He was the BEST host and had toiletries ready, little snacks, and water in the fridge for us! He even helped us with our bags and made us feel right at home! He was super responsive and made sure we had a great experience! One of our favorite Airbnb stays recently!! Would definitely rebook!

Super cute and convenient. Great yard for relaxing. Had a wonderful time