Pet-friendly vacation rentals in Shelter Island Heights

We had to find a place last minute due to some unexpected circumstances, and Lori was incredibly accommodating. We only needed it for one night to fit five of us, and the three-bedroom setup was perfect. She went above and beyond by offering early check-in and late check-out, and even brought us muffins and coffee since she knew we had to hit the road early. The space was cozy, clean, and very comfortable. The Wi-Fi was a little spotty at times, but it didn’t cause any major issues. All in all, a great stay — we’ll definitely be back next time we’re in town!

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!

Everything was wonderful! So peaceful, clean, and comfortable! The neighborhood was quiet and safe feeling. I personally loved that it wasn’t over cluttered with decorations! Plenty of room to put your stuff down and get to your vacation. Felt right at home!

Our family had a nice stay over Thanksgiving. The house was as described and clean on the inside. Laura was very responsive and answered any questions quickly. I only took 1 star off check-in as the property grounds were not well kept. This made it hard locate the driveway while also making the front entry dirty with all the leaves. All in all, we would stay here again as it met our needs for our family trip.

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!

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!!

Christine was a great host and we enjoyed our stay at the cabin!

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!!

Lovely stay at Sag Harbor with a beautiful home!

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.

Maura was an excellent host and the home was perfect! We enjoyed the weekend very much and cannot thank Maura enough for her kindness, responsiveness, warm hearted spirit, and for opening up her home to us. Will always keep this spot in mind for future SI adventures!

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.

Marta & Pete were great hosts. Left helpful instructions and a list of places in the area. The Cottage was definitely a great place to celebrate our anniversary. We wish we could have tried some of their oysters, but look forward to going back during the beach season when they're probably plentiful.

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!