Cottage holiday rentals in Shelter Island Heights

We loved this airbnb and stayed for 3 weeks. It sits right on the edge of the marsh with an extraordinary view. We greatly enjoyed how a short walk away is Chaffinch Island, which is a gorgeous park full of tides pools and hackberry trees. The space was clean and comfortable and Mary was a fantastic host. You can see a lighthouse on an island 3 miles out sea from all the rooms, even the main bed.

Great space and would be back!

Tabitha's place was perfect for our group stay. Right in the middle of town and perfect for what we needed for the week!

Great spot for a long weekend! Wonderful location close to the beach and local wineries. Richard was a great host offering lots of recommendations and clear instructions for check in and using available amenities.

Ivana and John are the most wonderful hosts! This was truly like staying at a family cottage and everything was just beautiful. John greeted us upon arrival and even had a bottle of wine for my husbands birthday! We loved staying here from the city because it was only a little over a hour to arrive and less than a hour to South Hampton where we had dinner. Also the little town is so so cute and we were able to walk over so quickly! We can’t wait to stay here again. Thank you again Ivana and John!

I really enjoyed my stay and the beach was very beautiful. Thanks Keith 😁

The place was charming, quaint, and exactly as described. It had a cozy vibe that made it feel like a home away from home. The location was perfect, with easy access to everything I needed. The host was incredibly responsive and helpful throughout my stay. Highly recommend this spot for anyone looking for an enjoyable experience!

This was our second stay here and it was just as nice as the first. Really responsive host and we love sitting outside at night with a drink enjoying the beautiful view. Nice spot where you don't even need to drive anywhere if you want to experience Mystic and even the seaport if you are up for a 20 minute walk. A+ again, thanks so much!

Leah was an incredible host, but a bit nervous at first. Our stay was absolutely amazing, and our dogs felt right at home in their cozy cottage. It was such a cute and comfortable place, and we’re so glad we chose Leah as our host. She went above and beyond for us during our stay.

This was my fifth stay in Jeanne's wonderful cottage! The cottage gets better and better each time I visit: a newly renovated bathroom, redecoration in lighter/brighter colors, etc. The home is extremely well stocked - every kitchen item you might need (including loads of glasses/plates/silverware, pots/pans, etc.), thick towels, extra blankets and throws, and lots of cleaning and paper products. There are plenty of cozy places to sit and relax, both indoors and out. The best thing of all is Jeanne herself, who is without a doubt the most generous host I've encountered on AirBnB. She is friendly, communicates proactively, and is quick to respond to any issues/questions. She truly opens her home to her guests, encouraging visitors to use the space fully and to make themselves at home. The cottage is an easy walk to the beach ane/or to town and is lovely, homey, and peaceful. I'll definitely return!

We had nice weekend at the cozy cottage. We loved that it was pet friendly and a short walk to the beach. Cameron was very friendly and responsive. She offered great suggestions for food and activities.

Wonderful time staying at Milton and Megan's. The location was perfect and the home had everything we needed and more to work remotely for the week. Thank you!

This has hands down been the best winter Airbnb I’ve ever had. Even though it has a beach theme, this could easily double as a winter wonderland cabin. I came here with my boyfriend to celebrate his birthday and before we left we were already planning our next trip back! This is hands down the cleanest feeling airbnb we’ve ever stayed at. They really put effort into making this place feel like a loved home. Everywhere you look theres a nod to the theme in home! The heating/cooling in the house is seriously impressive. The customizable fireplace upstairs (be careful on the stairs!) was a dream. Stargazing at night was incredible. I missed the sunset sleeping in on the incredible bed but the sunrise was AMAZING. Direct view on the front porch! Seeing the moon through the skylight while still being comfy on the couch and watching tv was absolutely terrific. From the endless amenities to the delicious food in the area, I can’t stop praising this place. Thank you guys for the great stay!

Great little cozy cottage on a beautiful river! Despite the rain, we had a great time. The house was within 30 minutes of everything we wanted to do during our stay. Kiki and Robert had everything we need and were hoping to come stay again sometime in the summer

Definitely is the best place that we have been , nice location ,super clean, kitchen is beautiful, the cottage is extremely private, bathroom super clean, in summer would be great to come back ,in other words absolutely fantastic!!! 100% recommended

Eglantine was a very responsive host! She answered immediately with whatever question I had and also very helpful. The binder provided also helped out a ton. There was a slight hiccup with the refrigerator turning off while we were away and we had to throw away some of our perishables because the internal temp of the fridge reach 84 degrees, but Eglantine responded right away when we contacted her about the issue.

Our visit was utilitarian. We needed accommodations for us, our grown children and grandchildren and a dog. But the site of the cottage, its charm, its comfort made us wish we were staying another week. James' thoughtfulness went beyond any other Airbnb hosts' that we've experienced. Everything we might need if we were staying 10 days was there, clean, labeled. Thank you, James.

I had a wonderful stay at Susan’s cottage. Check-in was easy, the cottage was gorgeous, clean, updated and fully stocked. Susan was a warm and friendly host who periodically messaged me to make sure all was ok during my stay. She also responded very quickly and was easy to get in touch with. I had a relaxing and quiet weekend away at Susan’s lovely cottage and would rebook with Susan again in the future. Loved every minute of my stay!

Felt right at home I’d definitely come again.

This house is absolutely perfect. It's clean, charming, has everything you need. The beautiful back yard has plenty of space and good stuff for kids to play with. Also, it's about a 30 second walk to the beach... neighbors are out on their patch of beach but yours is yours to yourself. It's perfect. We cannot wait to come back.

Had a staycation with my girlfriends and we felt right at home. They had all the necessary kitchen utensils to make dinner for my friends. Would highly recommend to anyone looking for a home away from home.

Fran’s rental is just as lovely as she is. Her place was perfect for three adults and when the Keurig went on siesta she brought a brand new one within a couple of hours. She thoughtfully chose the furnishings and provides top quality bedding and towels. The kitchen is very well equipped. This is a case of an owner who truly cares and is trying her hardest to provide an excellent guest experience and it shows.

The cottage is steps from the beach. You can hear the waves crashing in the house. The natural light inside is stellar and the wraparound deck always has both shady and sunny spots to relax, read, etc. There is a very useful laundry setup in a small basement utility shed and an outdoor shower with hot water. You are under 10 minutes walking to/from the ferry and harbor area. There are two water filters available for drinking water and the WiFi was strong and reliable throughout our stay.