Beachfront holiday rentals in Shelter Island

It was easy to find, plenty of parking, nice backyard space, the house was as described and pictured. We felt right at home!

Meredith’s cottage in Jamesport is the perfect North Fork getaway—spacious yet quaint, with incredible charm. The beach views are spectacular, offering peaceful sunrises and relaxing evenings. Meredith was a fantastic host—super attentive, thoughtful, and made us feel right at home. The location couldn’t be better: quiet and serene, yet close to everything from wineries and farm stands to local restaurants. It’s a quintessential North Fork home, and we can’t wait to return.

An amazing stay overall. It was comfortable for 6 adults. Spencer was extremely helpful throughout our stay — I had lots of questions and Spencer was quickly responsive. The house itself is beautiful and has that eastern Long Island charm. The backyard had lots of space and is well maintained alongside the pool. We also enjoyed a sunset evening at the beach which is just a few steps away. It was a wonderful weekend and I am certainly looking forward to staying here in the future!

What a dream stay! From the get go Vanessa was responsive and helpful with the booking. Our Girls Gone MILD Bach trip needed a home that would keeps us in vs out and this GORGEOUS home with it’s beautiful garden and pool/jacuzzi/patio made it the most memorable stay. We loved playing board games in the living room and dining at that warm long table! The kitchen was fully equipped with everything we needed as well (plenty of wine glasses for all the Wolffer Rose we got) and don’t get me started on the book in the basement rooms. There were towels, beach gear, umbrellas, and all the things you could possibly need for an unexpected rainy day or to have a good time at the pool/beach! Also the walk to the public access to the private beach was a short walk through such lovely neighborhoods! I’m hoping to come back and stay here again! The girls and I loved waking up to the pristine garden views and the occasional bunny that would hop across the lawn! We were definitely sad to leave ˙◠˙

Barbara’s place reminded me of the way airbnbs used to be. It felt like home-away-from-home. The accommodations were high quality and clean, and there were even some tasty snacks! We loved our stay. Everything was as pictured. Stony Creek was wonderful, and we look forward to visiting again next year!

We had a lovely stay. Eddie was always very responsive to any questions and ensured we had everything we needed. The house is spacious and was very clean upon our arrival. The outdoor spaces would have been great if we had better weather, and the backyard had privacy. I would recommend booking with Eddie!

My family and I had such a wonderful stay at this house. The house was immaculate and well stocked for our stay. Matthew and Celia are great hosts. We really appreciated the basket of snacks and dog cookies that were left for us and our fur babies (Thank you!). They truly thought of everything and it felt like “home” the entire time we were there. The views from the back deck are truly spectacular. We spent many hours sitting in the sunroom and out on the deck enjoying the sights. My pups enjoyed daily walks at the sea wall park that was steps from the house. I can’t say enough great things about our stay. Thanks to our hosts for sharing their beautiful home with me and my family.

I enjoyed every minute of my quick escape to Montauk! Check in and out was simple and convenient. The room was clean, private, and peaceful. Plus location has a beautiful view and is within steps to the beach.

We loved the location and the place was beautiful. Its was nice and clean. Definitely will be booking again

Fantastic location! We were literally a two minute walk from the beach. The studio apartment was as advertised and we would stay there again. We highly recommend!

Dan is the most responsive host we've ever had. Usually we got a reply within minutes or even seconds. He happily got the hot tub heated up for us when we needed it and replenished our towels within an hour of our request. That hospitality made our stay so much better. The home is beautiful! It's right on the water, and features lots of luxurious tile, a huge patio, a little dock and lots of windows and open space from which to see it all. We especially loved the hot tub. I wouldn't hesitate to stay again if I'm ever on Long Island again.

Loved Samy’s corner unit, which gave us a bit more privacy and quiet than other parts of the property. The studio was as described, with great light and well-cleaned prior to our arrival. Enjoyed use of the tennis courts every day. Only minor disappointment was that we were not yet allowed to use the pool, which we were told would be ready by Memorial Day (we were there one week prior). Still, a worthwhile stay and I’d come back and recommend it to others.

We were only there for one night, but it's a great location with great views of the water and easy access to the beach. Short drive into town for food, etc. It's a motel-style set-up, so we just picked up our access code when we got there and drove up to our room; all very easy. Our unit had clearly been relatively recently renovated, things were updated but starting to wear a bit. Overall very happy with the stay and the price was okay. Things we didn't love as much: There was no dishwasher, but there was a sign asking for dishes to be washed before we left. There is an AC unit, but not in the bedroom, so it doesn't keep things comfortable at night unless you have the door open. And Suffolk county sales tax wasn't included in the price; we had to pay for that separately for reasons that aren't entirely clear to me.

Great and responsive host. Home was lovely and we felt welcome. Host responded quickly to questions and requests. The home was very peaceful and relaxing. We really enjoyed the outdoor patio and pool area. I would recommend for a peaceful time away from the city.

We had a wonderful time. The weather was perfect. The view of the water was everything and was accessible from nearly every room. The home was modern and easily accommodated our large group. Yet it was cozy and beautifully appointed with all the amenities you would ever want. It is ideal for children with every toy imaginable. There was a highchair and a pack and play for our toddler and child appropriate dishes. The kitchen was fully equipped and had 2 sinks, 2 dishwashers and 3 tables for dining. The beautiful pool and hot tub were in constant use. Mary is very thoughtful and assembled a ringed binder with important contacts and suggestions for dining, shopping and entertainment. Although there was no beach on the property there are nearby beaches. The towns of Guilford and (nearby) Madison are charming and well worth visiting. Mary was very accommodating and responded promptly to several inquiries.

We had a great stay with Brian! Absolutely beautiful location and loved the pool.

Had an excellent stay at Eileen’s place. The house was extremely clean and perfect size for a couple. Beautiful view and surroundings. Only wish I had more time to explore the area. Would definitely stay here again if I return.

This is a beautiful private spot. It was so peaceful and quiet. The cottage was very clean, bright with a very soothing color scheme. Lauren was very responsive to any questions we had.

This was our second time staying at Jackie’s home and we can’t wait to return again soon! The space is perfectly located just a short walk from downtown Greenport. Everything you need for a relaxing weekend stay.

Our 2 day stay at the cottage was just what we’d hoped for our wedding weekend! Annalisa was so responsive and accommodating. A wonderful host, such wonderful hospitality and an amazingly stunning private retreat! Would definitely return!

My friends & I booked this for a girls weekend and we had an incredible stay. We could not have dreamed up a better place. Everything was perfect and as described. So much to do & so many unique amenities offered! We wish we had more time to try everything! If you are ever thinking of visiting Montauk, we highly recommend Brandon’s! Thank you so much!

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.

Tasha was an amazing host—quick responses and a lovely place. Would definitely book with her again!

Perfect place to unwind after a long day of exploring the North Fork 😍 Steps away from downtown Greenport and its charming restaurants, shops and bars. Not to mention we could find everything we needed and felt right at home in the beautifully appointed apartment :)