Holiday rentals with breakfast in Shelter Island Heights

Beautiful home in a lovely location with plenty of activities to do and sites to see. Michael and Lauren were very responsive to our questions and made us feel welcomed. They also shared a comprehensive guide to the area which was very helpful since we are new to Greenport. We hope to be back soon!

Great location, home was perfect for the occasion and the view/beach was beautiful.

I had a wonderful stay in July. The house is well-located between Bridgehampton and Sag Harbor. it is very clean and furnished nicely. The back yard and pool are sheltered and beautiful. The owners were very helpful and responsive.

I usually only stay with Superhosts but made an exception this time, since the place seemed so beautiful. 0 regrets. I am sure these folks will be Superhosts in no time. First - this place was CLEAN. The towels smelled fresh, the linens were clean, there wasn’t a lot of dust. Way better than most Airbnbs. The bed was comfortable too! Second - this is an outdoor paradise. The hosts gave instructions for the fire pit, even allowed us to use their fire wood. The outdoor fountains are so relaxing, and the VIEW is breathtaking. The furniture outside is well cared for and everything has covers so it stays dry and clean. You can hear the waves and watch the water all day from the deck, dining room, living room, or even the main bedroom. I spent a lot of time watching birds on the water with the binoculars! There are neighbors but at a distance so it’s private and quiet. This place is a slice of heaven and the hosts are absolutely wonderful. I will 100% rent again. ❤️

A lovely, updated ranch house with extra rooms in the basement and a spacious back deck and yard. The house is so close to the beach, quiet and secluded.

We had a fabulous time. The house was lovely and Linette was an excellent host. We enjoyed our stay and made memories with family—perfect vacay!

Amazing stay! The house is very clean. The pool was fantastic - it was heated which came in handy the last day. The kitchen was very well stocked. Would definitely stay here again!

This place was everything I was looking for, close to my job and shopping for everyday item. Jenn was very friendly and responsive. Would definitely stay there again.

Noel’s third floor apartment is light-filled, spacious, has a cute rustic vibe and is perfectly located. It’s across the street from East Rock Park (great for walks and runs) and walking distance to restaurants and an ice cream shop. The entrance to the apartment is through Noel‘s home – – no private entrance. Parking was incredibly easy—right on the street in front of the house! We enjoyed our stay very much, especially thoughtful touches like breakfast muffins and coffee. The apartment is full of interesting books and games and is very comfortable. Noel is a helpful host.

Great place, would recommend to other travelers. I had a few questions, but Michael was always quick to respond and offer solutions.

Everything was wonderful from check in to check out. Very Accommodating to our needs and schedule. Place was quiet and a perfect location. Would definitely book again. Thank you for opening it up to us.

Perfect place for my husband and I, our twins and my dad to stay for a family wedding. Would love to come back and just explore the awesome area in the future!

Excellent location-walkable to many of the restaurants and downtown. Alex and Josh responded pretty much immediately with any questions we had. Would definitely stay again.

We had such a lovely relaxing stay. It’s a charming apartment with everything you might need. Easy, convenient and spacious. Has a gentle vibe - just exactly like the pictures . It even has its own shy chipmunks and rabbits in the garden. Mystic is a beautiful town, with it’s glorious river, interesting history, museums, Seaport and pretty surrounds, - it hit the spot. Susan makes the experience so welcoming, with her openness, friendly approach and helpful advice and to top it all she baked us the most delicious muffins and cookies. Really lovely stay.

Airbnb was perfect distance to many of the attractions. Joanne left many amazing recommendations for restaurants and attractions that we added many stops to our weekend trip. Apartment was cozy, clean and on a very peaceful area.

Remy was always responsive to our questions and requests, and regularly checked in to see how we were doing. The location is excellent and very safe. It’s especially convenient for anyone visiting Yale, as you can easily reach any of the campuses from the nearby bus stop. I would love to stay here again if I have the chance.😊

Lovely b&b in a cute town with everything you could want/need. Michael was a great host and the breakfast was delicious. Comfy sleeping arrangements and just all around a lovely experience. Will definitely be back!

What a perfect spot in Shelter Island! Beth and team were amazing - we were visiting one night for a wedding on the island and the ceremony was at 2 PM the day we were arriving. I messaged Beth and she was extremely helpful with providing early check in to ensure we could get ready prior to the event! The actual B&B is beautiful - fantastic design, super clean, cool art and the backyard area with the pool is so dreamy. There is even a little workout area near the pool with a Peloton and a Lululemon mirror. Its a short drive from the North ferry, lots of restaurants and cafes and only a short walk to the beautiful Crescent beach. It is such a serene setting and I truly feel like I am on vacation.The room was beautiful and the bed was comfy, I am OBSESSED with the hand soap and have to find it for myself because it smells SO GOOD! I would 100000% recommend staying here and I will definitely be back!

Absolutely loved staying at the Oceanview Terrace this Easter weekend! Adriana and Yanni were fabulous, very friendly and responsive. The location was great, loved the cottage I was on, overlooking the Shinnecock Bay. Minutes outside of Southampton and other great local restaurants and shops. Very clean and I slept like a baby in the beautiful King bed with fresh linens with the best pillows lol!! I will definitely be back and recommend to all my friends & families.

Tom and Kate were lovely hosts. I was visiting the area for a wedding. When my scheduled arrival plan went awry, Tom and Kate were accommodating and flexible to meet my needs. The home was within a 5-minute ride to the wedding venue, making it a perfect place to stay. The home is beautifully renovated and welcoming. The bedroom is cozy and I slept soundly. The bathroom is small but suitable, and very clean. I enjoyed a wonderful conversation with the hosts in the morning, finding common interests with Kate in gardening and skiing. I would stay here again if I am fortunate enough to be in the area, and highly recommend it as an ideal place to stay.

Sue's place was very comfortable and she was welcoming. Her communication was Top 10 in response time and clarity. Convenient location for me as I wanted to be close to New Haven and Hamden to visit family. I liked the cozy guest lounge for reading.

Monika was a great host - really responsive and proactive giving clear directions and offering lots of local knowledge and tips for our stay. We stayed in the cottage which was quaint and so quiet. The location is beautiful. The weather was not great, but the house was cosy and comfortable. It is well located near restaurants in Southhampton and Bridgehampton and other attractions. Nothing is far. Would highly recommend.

we had such a lovely time at Jayne’s place! The room was very clean, we loved the garden and her cats! It was perfect for a little city getaway! We definitely want to come back:)

I have stayed with Barbara 3 times now. She is always personable and helpful. The setting of her home is lovely and peaceful.