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.

Super clean and comfortable. Kitchen had everything needed to cook at home. High end appliances. Conveniently located to shopping and restaurants. Beautiful, quiet neighborhood. Host was super responsive and friendly. One of our favorite Airbnb stays. Highly recommend and hope to return.

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!

Location was perfect for us- easy to find and close to things that are important to us (family in area, beach, shopping). Fenced yard made bringing our little dog that much easier- especially during the rainy day! Kitchen was well stocked thankfully as we were cooking Thanksgiving dinner (but not well stocked in the casserole dish, baking tin department-- which is usually not an issue for most people!). Decent coffee was supplied with a Keurig. Beds were comfortable. Everything was clean. I liked that he didn't leave a long list of what we needed to do before leaving as that is often a hardship when trying to leave a house with kids before a long drive. I would definitely stay here again.

Don't walk run and book your stay here. I mean wow! Mary's place is unbelievably beautiful, clean, comfortable, spacious, peaceful and very private. She has everything you need and then some. I'm so glad I picked this place to spend my 50th. You will not regret it. Thank You Mary🫶🏻

Very nice setup for two couples, a baby, and a dog - could spread out with bedrooms and full bathrooms on each floor. Comfortable space with amenities you'd want while traveling with a dog and a baby (fenced in yard, laundry, etc). Very walkable to all the shops & restaurants in town, and easy drives to wineries & breweries. The only drawback was that it was close to a fire station and the sirens woke the baby from a nap.

We had a wonderful time staying in this lovely secluded cottage. Jess and Zach thought of everything, the room was beautifully curated, and the bed was beyond comfortable. We will definitely return!

Beautiful, clean property! Bedrooms were spacious and the beds were so comfortable. We enjoyed the hot tub while the snow fell...its a perfect weekend getaway house. I wish I could come back in the summer to enjoy the pool. AJ was very responsive and provided easy instructions for easy check-in.

We had a wonderful stay at Peter's home. It was beautifully decorated, very comfortable and a quick drive to Springs. Access to the private clearwater beach was a plus! Thank you for sharing your beautiful home with us.

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

The moment we stepped into the house our holidays began: it got everything we needed and had such welcoming vibe. Clean, charming and cosy. And not to forget the great quiet location, just a couple of minutes away from the restaurants of Sag Harbor, the shops in East Hampton and the fantastic beaches. The host is highly responsive and solved a - minor - issue within hours. We can highly recommend this place!!

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!!

Our family of 4 had a wonderful time! We stayed for almost two weeks. The property is beautiful and puts you close to town of EH and Montauk. You are half hour or less away from Wolffer, Main Beach, Montauk, great shopping, amazing restaurants etc. We spent a lot of time riding bikes to the beautiful private beach and swimming in the heated pool. The house is clean, comfortable and has everything you need. Our girls loved to hang out in the sunroom and play basketball in the backyard. Can’t say enough good things about Ellen and how great of a host she is. Highly Recommend!

I had an amazing experience staying at this Airbnb! Luz, the main host, was absolutely wonderful—so kind, welcoming, and incredibly helpful throughout my stay. She went above and beyond to make sure I had everything I needed and even took the time to recommend some great local spots to visit. Her hospitality truly made this stay special. David was also fantastic so professional and accommodating. He made everything so easy, from check-in to answering any questions I had during my stay. It’s clear he takes pride in ensuring guests have a great experience. The space was spotless, beautifully decorated, and just as described in the listing. It felt so cozy and inviting, and the little details, like the complimentary snacks and toiletries, made all the difference. The location was also perfect. I couldn’t have asked for a better stay. Luz and David are a fantastic team. I highly recommend this Airbnb to anyone looking for a comfortable, welcoming, and enjoyable experience.

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

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 had a great stay at this cottage- it was a perfect size for our family and was extremely clean, warm and comfortable. We especially enjoyed the quick walk to the beach, and proximity to town. Hosts were very friendly and responsive but never intrusive. Would highly recommend.

Madelaine’s cottage was the perfect location for our weekend in Water Mill! The house was cozy with a spacious and private backyard. The location is centrally located, and we were even able to walk to and from breakfast and the farmers market. I would recommend the cottage and would absolutely stay again!

Marta and her husband are extremely responsive to questions or any issues that may have arisen while I was there. They were very friendly, great location and is so close to where I am working. Centrally located to the village as well as many other villages and the town is full of things to do. Not so much in the winter but the Eastern end of LI in the nice weather is amazing.

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

The bungalow was a wonderful little winter retreat. The sunsets over the water were stunning, and beach access was a short walk away. The house is small and cosy but exactly what I needed, with the living/sleeping/kitchen spaces separated enough to feel comfortable. The beds were memory foam and were very comfortable. WiFi was great and I was able to get a 2 monitor WFH set up on the kitchen table. Driveway is very narrow but I could fit my large sedan down it and could fit 3-4 cars if the street parking was taken up. It snowed while I was there and a shovel + pet safe salt was provided. Dogs sadly aren’t allowed on CT beaches, but the Charles Wheeler Wildlife Area is a 15 min walk away and dog friendly and also offers gorgeous sunsets. The neighborhood is quiet and respectful, with a cosy beach town vibe. I want to come back in summer and see how gorgeous the view is in the summer!

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 had a great fall getaway with our adult children and small dog here. Lots to do nearby: good food, beach walks, trail walks, water views, sunsets and sunrises. Exactly what we look for in our annual fall beach weekend: we've done Cape Cod, Boston North shore and RI before, and CT shore is just as much fun and as pretty. House was perfect for 5 adults: we made dinner in the well equipped kitchen one night, our 12 lb dog felt right at home in the small yard. We didn't use the grills or the outdoor shower that is here, but def was nice to know they were there and available. The nights we were there were a bit chilly, but the space warmed up nicely. def is on our short list for next year!