Search Vacation Homes in Shelter Island

"The house was so cute and a great location. Everything was easy to deal w and Pam was very flexible with timing. Will certainly hope to stay here again!"

"Celebrated the holidays with my grown children to be near my dad and brother. The house is lovely. We had a wonderful time. My daughter suggested we come back in the summertime to take advantage of the amenities - beautiful pool and nearby beaches. Highly recommend!!!"

"Very nice place. Would definitely stay there again (actually this our second stay at the property). Clean, well equipped and the pictures are accurate."

"Pretty gingerbread cottage, well appointed. Lovely area, 2 min walk to the beach. Owners super helpful. Overall beautiful, serene, highly recommmend."

"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."

"I found it cozy, comfortable and very peaceful. Bonus wildlife visits of deer, geese and turkeys, Most people will understand this accommodation as quality “clamping”."

"Perfect location!"

"Our group of four friends in our 50s loved our stay here. Heather was a responsive, welcoming, flexible host who left us a card, bottle of wine and a prepped wood pile in the fire pit. The decor was tasteful and beautiful, clean and modern. The mattresses were firm, which we liked. We made use of the comfortable couch on the deck as well as the gas fireplace in the living room. The location is lovely and we had a short, 5-minute walk to the beach. Birders would enjoy the tremendous diversity of...

"Got away for a girls weekend and this was perfect. It was close to wineries, and a short Uber away to Greenport. The house was comfortable, clean, and private with enough space for all 8 of us. The outside was also beautiful- right on the water. Highly recommend!!"

"The house was great - just as listed and very comfortable / kid friendly. There wasn't a whole lot to do in the area over the holidays but we enjoyed the house, trampoline and jungle gym."

"Perfect spot for a weekend on the North Fork"

"This place was great all around, really nice open kitchen and sunset by the pool in the backyard was very serene; easy to get into town, the beach, Sag harbor, Amagansett, really great location within East Hampton"

"We had the best time visiting Sam & Matt’s place in Southold. The house is the perfect size for us- 3 adults and 3 kids plus 2 dogs. And it was an ideal location to explore all the north fork has to offer. We can’t wait to return!"

"Old Saybrook is a nice little CT beach town and the property is perfect for a small family. Check in and everything was very easy and the hosts are super responsive if you need anything or have any questions. We'll definitely be going back when we need a couple of days away!"

"Great stay and wonderful property. The first stay that didn’t have a book and list full of restrictions and checkout instructions. After a whirlwind weekend celebrating our daughter ‘s engagement, this was a welcomed surprise! Everyone enjoyed their stay, including our two labs. Great fenced in yard that gave them plenty of room to exercise. We will be back!"

"Nice vacationing place for the family with young children"

"This property was just what my family and I were looking for. A quaint and quiet house with a small town feel. We stayed for NYE hoping to get away from the loud chaos we’re typically faced with at home and this location fit the bill. Pros: I’m not sure how this changes in the summer months but things were mostly quiet. There are restaurants, coffee, and food shopping all within a 5 minute drive. The home itself is pretty small, so for the 4 of us- husband, 17y/o, 9 y/o, and myself, it was...

"This cottage is Comfortable, clean and fully stocked on a private street with a beautiful short walk to the beach. We were only 2 but house could easily sleep up to 8 guests. Large backyard with tranquil outdoor setting firepit and Barbeque. Host is very responsive welcoming and helpful. The nearby Main street has many restaurants and shops as well as Wine vineyards. Will definitely be booking again in future. We found a new love and that is Jamesport. Thank you Kelly!"

"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."

"The cottage is a perfect cozy stay on the water - we stayed in the winter and still were able to enjoy the sand and the sunrises right outside the window. House is well-appointed and well-located within area with access to restaurants and shops in Clinton, Madison, Westbrook, Old Saybrook, etc."

"Best affordable hotel in Montauk"

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

"An amazing stay with our girls!!! Can’t wait to go back!"