House holiday rentals in Shelter Island

We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!

Wonderful weekend stay. Charming.

Michael’s place was amazing, means a few friends stayed this weekend for my birthday. He was always willing to help and very accommodating! The house itself is so beautiful and had everything we needed! It was our first time in The Hamptons and he gave us tons of recommendations!

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.

Our hosts were amazing. They responded quickly. They were very welcoming to us and provided easy-to-follow instructions. The location was great and the house was lovely. I would definitely stay here again.

We had the most beautiful weekend stay at Tim’s home! Everything is accurately described and the pool and hot tub were amazing!! All the beds were very comfortable. Was perfect for a 5 girl weekend getaway!! Tim was incredibly communicative and checking in was a breeze. The location is PERFECT in East Hampton!! So many amazing restaurants and bars nearby. 100% will stay here again for my next Hamptons trip. Thank you so much Tim!!

We had a lovely weekend at Rachel's cozy abode! The home was perfect for a few of us working remotely for the week. We were able to enjoy the peaceful backyard & pool and the house was stocked with all the kitchen essentials we needed to cook a few meals at home. The location of the house is also great--we enjoyed the quick drives to nearby beaches and our dinner outings. Rachel was communicative, kind, and responsive. We hope to be back for another getaway in the near future!

This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!

Erica and Janson's place was perfect for our group of eight to attend a wedding in the Hamptons. You cannot get closer to the North Ferry to Shelter Island and there are many restaurant and shopping options within walking distance... the pizza place next door is open late, PORT restaurant (across the street!) is great for waterfront drinks and dinner. While we didn't use it, the LIRR station from Manhattan is also 500 feet from the front door. Ample parking was appreciated and the place was spotless. Thank you Erica and Janson!

Beautiful house, perfect for a getaway to the north fork. Very close to a beach. Very clean and comfortable. Elizabeth is a great host. Highly recommend.

This beautiful home did not disappoint! There was lots of space for our group of 7 ladies to eat meals together, sit outside for coffee, play games and sleep in the comfortable beds. Lots of amenities including utensils, cookware, plates, glasses, towels, etc. We walked to beach and it was a quick drive to town. We are already planning our next year’s visit! Thanks for being super responsive Adam!

We had a fabulous stay at this adorable cottage. It had everything we needed and more. Great spaces indoors and out to hang out, walkable to one of our favorite wineries, other wineries & restaurants close by. Appreciated having a tandem kayak to use & explore Goose Creek. Enjoyed watching birds, including Baltimore oriole parents in a nest in the backyard. Would return again. Thank you!

I have a lovely time at this charming home. It was exactly as pictured and advertised. The home is warm and inviting and I was very comfortable throughout my stay. The backyard has a beautiful view of a lake. I spent quite a bit of time on the rear deck reading and getting distracted by that view. Locally there is Greenport Village, Orient Point State Park and Inlet County Park to name a few of my favorite outings. Thank you to my host for being so responsive when I called with a minor issue one late evening. I hope to return for another stay one day in the future.

Anne Marie’s cottage was exactly as described right along w/the peaceful surroundings, lovely views of the water and close proximity to beach and town. She gave us recommendations for local gems, and we thoroughly enjoyed our time. We will certainly try to get back again. Cheers to the host 🥂

As a native long islander I enjoy finding great properties I can bring my family to to take advantage of all long island has to offer. This was the DREAMIEST beach bungalow!! The bedroom with the two beds was just my favorite room especially since we visited off season. You cannot beat this location. I can't wait to book again during high season! Thanks for sharing your home with us !!

This is one of the most soulful places to stay on Long Island, Greenport, our second visit. A true family gem with laidback vibes and stylish features.

There’s so much to love about this charming open plan beach cottage! We especially enjoyed the water views, hearing the birds, and eating on the breezy porch. It was sparkling clean and stocked with everything you’d need, from comfortable beds and towels to many thoughtful essentials like hand and dish soaps, tea and coffee pods, paper towels/toilet paper, and shampoo/conditioner. Eileen is a gracious and responsive host — she was particularly understanding when we had to reschedule our visit. Thank you for a wonderful stay, Eileen, and we hope to return!

We had a wonderful stay! The master suite is huge and the bathroom is dreamy. We didn’t really use the backyard bc it was winter but it was great for our pup! Kitchen was small but did the job (no microwave). We had issues with streaming on the “guest” accounts but we always travel with our own firestick so we were fine. The beds were super comfortable (firm memory foam type) but it was quite bright in the upstairs bedrooms in the morning bc several of the windows had no covering so if you need a blackout situation for little ones pack accordingly. We were able to put the provided pack and play in the closet which was fine for us! We would definitely recommend and return!

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.

Ashley’s house is the perfect get away. I booked this house for my family to stay for my wedding weekend. My mom had never stayed in an Airbnb before and I’ve never seen her so happy and relaxed. She truly enjoyed her first Airbnb experience at Ashley’s place. It was exactly as described and the view is beautiful. Ashley was very responsive and made sure to answer any questions I had.

Nice private quiet location but close to beaches and main street shops and restaurants. Convenient to visit many local vineyards within 15 - 20 minutes. Home is comfortable and nice set up.

Had a lovely time in the Hamptons! Tasha was an amazing host- easiest check in/out, very responsive, and gave great recommendations for places in the area. Would love to stay here again!

I had a wonderful stay! The place was exactly as described—clean, cozy, and well-equipped. The host was friendly and responsive, making check-in and check-out super easy. The neighborhood was quiet and convenient, perfect for relaxing after a day out. I would definitely stay here again and highly recommend it to anyone visiting the area!

We had a wonderful stay with my family! Everything went smoothly from start to finish. The check-in process was easy and communication was clear and prompt. Anisha and Rob are great host, very friendly and responsive. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed for a relaxing stay. The house is spacious. I really appreciated how well the place was maintained. I would definitely stay here again and highly recommend it to anyone visiting Southampton!