Pet-friendly holiday rentals in Shelter Island

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!

Andrew and Kenneth were excellent hosts. Some of the most professional, responsive and attentive I have experienced. The home is cozy, and the space is really well used and appointed. Some of the appliances are a bit quirky -- like the washer/dryer, which isn't very effective; and the stove/oven which the hosts are aware needs some repairs. The location is lovely. Be prepared to listen to the ducks on the lake. They can be loud even during the night. The outdoor shower was the icing on the cake for me. I nearly stayed longer, except I had another opportunity overseas.

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!

In all my years using Airbnb Kim is by FAR the most warm and welcoming host I’ve worked with. Her home is the perfect beach cottage escape. Unfortunately we had an emergency and had to change our plans- Kim couldn’t have been more gracious and understanding. We didn’t get to relax and explore but the entrance to the beach looked picturesque and I absolutely plan on booking Kim’s place again.

John’s place in East Hampton was perfect for our MDW getaway. Beautiful property, clean and cozy cottage, and very close to restaurants and bay beaches. Great area for running. John was great and very helpful throughout our stay. Highly recommend!

Had an amazing time! The location is great. On a very quiet road and close to the water, incredibly peaceful The house is great, everything you could want and also everything is very simple to figure out. So you feel right at home instantly The layout is great with indoor/outdoor living being seamless! The pool was lovely and warm, sauna was great and hot tub perfect! Couldn’t ask for any better, Brilliant attention to detail and a lot of effort to make it a great place for anyone to stay! Benjamin was lovely to deal with, will definitely stay again!

Just returned from an awesome stay at Travis’s cottage. Travis and Morgan are great hosts and were very helpful with providing local suggestions and prompt communication. The property is great and was the perfect home base for our first trip to the North Fork. The location is ideal: quiet, charming, and centrally located to everything (wineries, beaches, breweries, farms, and great restaurants in Mattituck and the nearby towns). As a family with two young kids (6 y/o and 18 months), the fenced yard was a huge bonus - private, peaceful, and perfect for relaxing while the kids played safely. The house itself is cozy, clean, and full of character. We’d absolutely stay again on our next visit to the area.

Absolutely beautiful home and wonderful experience!! The host was quick to respond and the amenities were excellent. There was zero lack! Would definitely return for another stay!

Lisette's listing was great! It was perfect for a family vacation. Lisette was super responsive and friendly. The house was very clean and looked even better than the pictures. The pool was fantastic as well. Highly recommended.

Marta could not have been more accommodating! She was responsive and provided everything we needed. She even went the extra mile and insta cart-ed garbage bags and paper towels when we ran out. She could not have been a kinder host! We had the best weekend and would HIGHLY recommend staying at Marta’s place! We will definitely be back!

Ashton’s house a very comfortable and extremely clean home. It is spacious, allowed tremendous privacy and met our needs perfectly for an amazing family vacation. Everything was just as explained with no surprises. Great stay and a very accommodating host.

Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

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.

Great spot in Hampton Bays! The house was as described and in a very cute and walkable neighborhood. Super close drive to the beach and a couple of local restaurants and eateries. Loved how private the spot felt too! David’s done a wonderful job with the backyard, so you get the comfort of having close neighbors without the intrusiveness. Pool was awesome. We definitely enjoyed it!

Went with a bunch of my girlfriends and had such an amazing time! Lisa's home was amazing and we all felt right at home! So happy that it was a common ground where my girlfriends and I were able to gather around and create unforgettable memories.

Loved the stay! Exactly what we thought it was - extremely convenient and cozy. Plenty of beaches to walk to and the food options were plentiful. Would definitely stay again.

Cannot say enough great things about this house. I’ve stayed in many AirBnBs and other home rentals over the years and this was one of my absolute favorites. The house is beautifully updated and was extremely clean. The kitchen and bathrooms are gorgeous and have everything you need. Beds were so comfortable and the room darkening shades are a rare find in a vacation rental. Close to Greenport town and lots of wineries. Backyard was beautifully landscaped and was amazing for our dogs to run around. We will definitely stay here again!

Lovely fall weekend at Frank's place, just a few blocks from the water and a small beach, and easy walking distance to town, shops and restaurants. A cozy home away from home!

We had a wonderful weekend. Great place to stay. Would recommend it highly.

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!

My friend and I had the most wonderful stay at Carey’s beautiful home. It looks just like the photos and is the perfect charming stay for 2 friends or couples. The location is fabulous—about 10 minutes to all the attractions of Southampton but also very secluded. We loved walking to the beach at the end of the road, visiting Lunch for Lobster Rolls, taking tennis lessons close by at the water mill community center, and even driving about 20 mins to Sagtown coffee in Sag Harbor. On sunny days we enjoyed reading our books out by the water. Carey was a fabulous host and was extremely communicative from the minute we booked all through our stay. For any minor things that needed attention (like a changed lightbulb or sticky doorknob), she had a lovely local handyman come by within a day, all the while communicating with us to ensure it worked with our schedule—what more could you want from an Airbnb host?! We can’t wait to hopefully return soon.

Wow!! The perfect peaceful getaway that is close to everything!! Tucked away off the road the house is quiet with a beautiful yard. The interior is both stylish and comfortable. The kitchen is extremely well outfitted. Andrew is a great host and an excellent communicator. We only wished we could have stayed longer!! The question isn’t will we come back, it’s simply when!

We had a great time at Adam’s place! The apartment was cozy, clean, and comfortable — perfect for a relaxing getaway. It’s just a quick 5-minute drive to Sag Harbor, which made it super convenient.

It was the perfect spot for a getaway weekend. Easy access to wineries and restaurants. Would definitely stay again.