Kid-friendly holiday rentals in Shelter Island

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.

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.

Isabel's home was in a beautiful location with easy accessibility to town and had all the necessities. Home is neat and clean and Isabel was responsive to our questions. Just a heads up.. although the post says air-conditioning it is not central air and we visited at a time when the window units were not in place as yet because the weather had been cool up to that point. We arrived on a warmer day so we could have used it and although there was a ceiling fan in the kitchen and upstairs bedroom there is none I. the downstairs bedroom. perhaps supplying a floor fan would be helpful

We thoroughly enjoyed our short stay. The house was comfortable, clean, well-stocked, and conveniently located. We didn't have enough time to enjoy the backyard but it looked fantastic. Check-in and check-out were easy and straightforward. Would absolutely stay here again.

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 !!

our group found this place when planning a trip to Montauk, and while we did make it to Montauk as well, Greenport was also a pleasant surprise. Great community and quaint town! The place was amazing too! clean rooms, very cozy. And a complimentary wine bottle! Highly recommend!

This is a very clean and comfortable house with good quality linen and towels. There is minimal clutter and the place is well furnished with everything you need in the kitchen. The house gives off very good vibes. The view from the French windows across the deck to the little bay is exquisite. All in all, highly recommended.

We had a great weekend at Nicholas’s place. It was very peaceful in the woods, and we enjoyed using the record player and looking through the books spread throughout the studio. Nicholas was very responsive when I texted with questions and we used his provided recommendations to find breakfast and dinner. We’d definitely stay here again!

Incredible location! Walking distance to the town. The neighborhood is very quiet and we felt very comfortable all weekend long. Carole and Rich are wondering hosts, and the apartment had everything we needed. We would recommend!!

We were a party of 5 women and we had a wonderful stay. The location was great, the unit was spotless and spacious, the kitchen had all the necessities, the towels and linens provided were very nice quality, and Amanda was a wonderful host and very responsive. We were able to check-in early which is always an added bonus. The only thing we would recommend being disclosed is that the train is right behind the location and came through pretty early in the morning and was quite loud. Also worth mentioning in the description would be the amount of stairs to get up to the living area of the home. This was not an issue for us, but could be difficult if you had large suitcases and heavy items to carry up. We would definitely recommend and would stay again.

It was such a pleasure spending a weekend in Claire’s studio. The studio is very clean and comfortable, and my wife and I particularly appreciated the kitchenette, which allowed us to prepare a dinner one night and make our own pour-over coffee in the morning. We also loved hearing the birds as we woke up in the morning. And the location is terrific—an easy walk to the Southhold town center and a quick drive to other surrounding attractions like Greenport, nearby beaches, and wineries. Highly recommend!

Danielle’s place was perfect - easy to check in, good communication, great location, super clean and comfortable. Thank you, Danielle!

It was a great stay, my second time staying here and Roisin is quick over communication and answering all the questions we had. Overall, great location and easy to get to!

Great venue. Hope to be back next year!

Kate & Janelle were exceptional hosts. We had a minor technical issue upon arrival and Janelle was immediately available to help us troubleshoot. This beachside condo was the perfect place to stay for a long weekend. The space was spotless. We loved the decorations and ocean view. The highlight, without a doubt, was the east access to the beach. We can’t wait to come back!

The Beach Plumb was lovely! Everything was as advertised. The distance to town and the beach, the spacious layout, and the amenities are among the things that made our stay great

Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!

We had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace

Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Adam’s cozy cottage was exactly what I needed! I was visiting for a work event and I needed a quiet base-of-operations to answer emails and take calls. The unit was pristine, much more space than I anticipated. Hot shower, full kitchen, comfy couch, and a big bed. When I was ready to turn down, the stillness and quiet was breathtaking. Complete darkness. Whether you need an extended office / room for a business trip like me, or if you want a quiet, isolated getaway near Sag, this is the spot. Thanks Adam!

We had a great stay! Instructions were clear and the home had everything we needed.

Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!