Pet-friendly holiday rentals in Shelter Island Heights

Lori was an amazing host. She coordinated with me on everything prior to checking in. I explained that I would be using her home for a small surprise birthday party and she even offered to do some decorations or help out any way she could. Way above and beyond her responsibilities as a host. On top of that she set up a fire pit with firewood and even left a s’mores kit for us. The most amazing thing was she left a birthday card and gift for my girlfriend. It was completely unexpected and we were so appreciative. The home was very clean, cozy, and had everything that we were looking for.

We had a very peaceful few days here. The home was just a short walk to the beach and to nearby restaurants and bars. We loved waking up and spending time in the sun room before going out and exploring Montauk. Adam and Matt were extremely welcoming and responsive and we would definitely recommend this spot for anyone visiting montauk!

Lovely, quiet home, with well-appointed furnishings, and comfortable beds.

Ritestay was a great place. We didn’t spend much time there because we were there to see our daughter. Would be perfect in the summer!!

Ed was great at communicating, house was everything we could have asked for. Would definitely book again!

We were so excited to find this house available again. We were here a few years ago and always wanted to return. It was just as wonderful as we remembered. Iris is a great host. She meets every request with prompt enthusiasm. We highly recommend her and this beautiful home.

We came back to stay for a second time and hope to be back for many more! The place is exactly as advertised, beautiful, and an easy walk into town. Marianne and Stephen were super flexible with a few requests we had around the stay and so easy to communicate with. Greenport is the best and this home is amazing - you won’t regret booking here!

Beautiful house- even better than the pictures. We were two families with young children. We loved the open concept with plenty of space for the children. We were able to walk to town for dinner (the walk home is uphill FYI). The house was well stocked and every detail of furnishings was coastal and cute. The host is extremely responsive and helpful. We definitely will stay again when we are in town.

It was a lovely stay. Great location. House felt like a home and had great vibes.

Maher’s house was an amazing peaceful experience. I enjoyed my time there and he had great recommendations to restaurants and activities! He was very responsive with all questions we had. I will totally stay here in the future if I can get the chance again!! Thank you Maher!!

Dorina’s home was the calm, peaceful reprieve from the city we were looking for. Her home was so comfortable and she went above and beyond to make sure we had everything we needed. The backyard was a little oasis with a large pool (with floats!), several (6 I think) lounger chairs, two 6 top tables in different areas and a functioning grill. We spent most of our time here! Dorina was fast to respond, helpful with recommendations and overall what you hope to have in a host. We would definitely come back to Dorina’s home!

Had an absolutely wonderful stay! Location is perfect and Jaime was incredibly friendly throughout!! He let me know that they had everything we would need.. but as a self-described obsessive packer I didnt listen. He wasn't kiding! They had beach chairs, umbrellas, and everything else you need for the perfect beach day. I brought an entire wagon of stuff and used one bag. It really is an awesome little find!!

Thanks to Giuseppe we can have meaningful time in there. It couldn't be better!

Our family had an amazing stay at Christian’s. The house is beautiful with a great pool and backyard. We ate on the back patio every night. It’s a two minute walk to East Quogue and a 12 minute drive to the beach. It was a dream. We’re already planning our next stay.

House is well represented. Spacious, very clean, and great location. Good for families or groups of friends.

The stay was fantastic, we wanted a quick getaway for the weekend, and their home was the perfect spot. We enjoyed the space by the fire and the cleanliness of the spaces. We would love to come back for a longer stay.

The place is roomy and clean. The bed is comfy and the shower is great. There were juices and sodas and water in the mini fridge, a coffee maker with coffee and some wrapped snacks. A comfortable place to stay in a very pricy part of Long Island if you prefer a home over a hotel. We were only there for the 2 nights of our stay since we were out all day and for that it was perfect.

We come to Montauk often & loved this spot. Walkable & convenient to town plus a beach pass. The accommodation had plenty of space for a family with convenient parking. Highly recommend!

We had a fabulous time! Can't wait to come back. Was equally perfect for two toddlers as it was for four adults! Beautiful property, amazing hot tub, comfortable beds, great kitchen... everything was lovely.

As always, we love our stay at the cottage. It’s becoming our home away from home when visiting our son. Thanks for all our goodies! Always a great surprise! Have a wonderful Christmas. We’ll see you next year I hope.

This place was cozy and quaint. We were only missing a can opener! You too will like it! I would stay here again

We had a great stay at Jess and Zack’s place for my birthday weekend on the North Fork! They provided clear directions ahead of time on how to find their place and how to check in. We were greeted by the sweetest pup. The space was spotless and very comfortable. We had a fire in the fire pit one night and that was excellent. It’s super close to lots of great restaurants and wineries! I would recommend their place to anyone looking for a quiet and peaceful getaway!

Judy’s place is super lovely and in a fantastic location! Easy walk to the beach or quick ride into town. Easy to communicate with as well. Highly recommend!

We loved our stay in Westbrook! Mia's lovely home exceeded our expectations in terms of decor, furnishings, cleanliness, comfortable beds, and well-stocked kitchen and bath ... all in a quiet and private setting. The house was especially well-situated for us. We had tickets for a special theater performance at Gillette Castle one evening, and then had to be in New Haven on the next day. All were easy drives. And, there are amazing fine dining options nearby. We'll definitely try to book this wonderful place any time we have events in the area. Thank you, Mia, for a magical Autumn weekend in Connecticut!