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.

Review for an Airbnb Stay Our stay at this Airbnb was absolutely fantastic! The property exceeded our expectations, with everything impeccably clean, comfortable, and thoughtfully arranged. The hosts were exceptionally kind and attentive, always ready to assist us with anything we needed and providing excellent recommendations for the area. Their warm hospitality made us feel right at home, and their attention to detail was truly remarkable. This was one of the best Airbnb experiences we’ve ever had, and we would highly recommend it to anyone. We can’t wait to come back!

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.

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.

Gloria was a very amenable host the place worked out great for us and our two dogs and we were able to entertain a few friends and cook an amazing dinner

The place was perfect for our getaway weekend! The house is super spacious, very clean and has everything one may need to enjoy your stay. The host was friendly, accommodating and always available to answer any questions we may had. Will absolutely recommend this place

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.

A great place to stay! Very enjoyable!

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.

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!!

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!

This house was fantastic! We cooked a full Thanksgiving dinner here! The house was well stocked with everything we needed, from kitchen essentials to paper products. The layout of the house was great. Jane was very accommodating and made things easy for us! The house was immaculate and met all of our needs. I hope it’s available next Thanksgiving! Perfect location! Close to town, yet quiet and private! It was my granddaughter’s first Thanksgiving and I’m so glad we had this house to celebrate in!

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 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.

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!

Our second stay at the cottage - it's been a very convenient find; appreciate being able to use as our home base while we explore the area, and especially being able to bring our dog! Small but has been fine for the two of us, have used the kitchen multiple times as well.

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

Judy and Joe’s home was the ideal getaway for our family’s extended Thanksgiving break. It had all the comforts to make us feel right at home, with a perfect location for exploring everything from South Hampton to Montauk. The private beach access was the cherry on top, offering the perfect spot to soak up the sun and enjoy the ocean waves. We can’t wait to return!

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!

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!