Search Shelter Island Cottages

"Eunyoung and Mark have a beautiful home and have created the best “home away from home” for travelers. We thoroughly enjoyed our stay and look forward to returning next summer!"

"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."

"I was in the area for my niece's college graduation at Wesleyan University and loved the chance to explore this beautiful part of the country. Being so close to the water in Old Saybrook was amazing, and the house itself was both fresh and cozy. The hosts were very responsive, and the only issue (which they acknowledged in advance) was that a portion of the fence was missing, due to a recent storm. That said, they were up front and apologetic, knowing that I'd booked because my dogs were along....

"You have the opportunity to attend a graduation party at the Hamptons, where everyone had to find their own accommodations. The location is essentially located to town to the water and beautiful scenic paths. The host insured that the home was exceptionally clean and amenities provided. Not to mention accommodating due to last-minute change in schedule."

"Beautiful studio apartment and truly a retreat from our busy work schedules. Nice response from host when we had questions. Lovely location and truly inspiring..."

"Tucked away near the sound….a piece of paradise ! Truly a beautiful place to unwind and enjoy all the North Fork has to offer . Centrally located on the North Fork, but easy access to a spectacular beach . You will leave refreshed & trying to figure out how soon you can return ."

"I booked this for a sister weekend. It was perfect for what we needed. It appears that the house was built to be a summer getaway, so it is pretty basic and no frills and comes with all the creaks and quicks of an older house. The living room is perfect for hanging out and the four chairs make it easy to rearrange to suit your needs. The kitchen is nicely stocked with everything you would need to stay with a family and the dining room is spacious enough to easily accommodate everyone staying...

"This cottage is so adorable and just a short walk to the beach and a local convenience store. This makes it easy to park the car and just walk to get coffee and such. We stayed in October so not much open this time of year, but we were in the area for a family wedding so not much time to hang out anyway. This was the first time I've rented on Vrbo, so I wasn't sure what to expect as have read a lot about obnoxious owners with tons of rules, but Brett is super-chill with only a couple of things...

"What a beautiful relaxing weekend getaway with friends. The view was beautiful and the place was clean and comfortable. We would stay here again!"

"Relaxing and beautiful sunset views , Clean and floor plan one floor plan was perfect ! Spacious and so nice to relax on this vacation ! Close to everything we needed !"

"The cottage was quite wonderful with a large kitchen and comfy porched living-room. Scott was very quick regarding any communication. The only thing in the description that I would add is that " you'll need to bring your own towels and bed linens". It wasn't a problem, but our airplane carry-on bags only were already packed. We made our adjustments and ended up checking a bag, no worries. Just a thought. We thoroughly enjoyed its quiet and relaxing location."

"Very intimate cottage setting, lovely beach scenery, walking distance to the beach, feet away from hearing the crash of the waves. Short drive to grab whatever you have forgotten or need to enhance your stay in this tiny home. Great location to unplug, energize, and bond with your family. You can create the quality time you miss out on in the world today, you will not have the distractions of television, internet, or gaming."

"This is beautiful cottage, and the location is perfect for all the vineyards. The house was VERY clean, and the garage is a great place to hang out and relax too. My Husband and I will be booking again very soon for another getaway. Thank you so much."

"Returning to this property with our dog. Love being near the water and still close to everything. Brunch at Love Land is minutes away. My dog loves wineries and there are many dog friendly options near by. Dinner at North Fork Table is not far away. Highly recommend!"

"My friends and I had a great time staying at this adorable cottage! The beach is so close and the parking pass is a lifesaver! We also loved making a fire and relaxing in the backyard. There was plenty of room in the kitchen to cook while spending time together. Will definitely book again!"

"The lake house was a perfect retreat, perfectly located to town, train, trails and beach. We can’t wait to visit again !"

"Best affordable hotel in Montauk"

"Good family friendly resort! Hope it’s a heated pool.. Easy Check-out before 11:00 am!"

"Very nice location and nice condo"