Apartment vacation rentals in Shelter Island Heights

This is a lovely upstairs apartment about a half mile from a small marina with several good restaurants. You will want to get to the beach in Madison, a state park, rather than the Clinton beach which has high fees for non-residents. With that said, the gate is not attended after 6 pm when I sat and ate a lobster roll and then explored some of the history plaques to be found on the point. Catherine’s place was the perfect site for me to rest after a Hoffman retreat.

Great cozy place with a lovely view of the marsh from the bedroom window. Bruce was a kind and thoughtful host, the place was very clean and easy to get in and out with clear instructions and labels on everything. Thank you !

“A Wonderful Stay!” I had such a pleasant experience at this Airbnb! The space was clean, cozy, and exactly as described. The host was incredibly welcoming and attentive, making sure I had everything I needed for a comfortable stay. The location was perfect—quiet and peaceful, yet close to everything I needed. I especially appreciated the thoughtful touches throughout the space, which made it feel like home. I wouldn’t hesitate to book again—highly recommend! Feel free to customize it with any specific details about your stay!

Thank you for the lovely accommodations! The space was well appointed and we loved the attention to detail with the decor and amenities. It was the perfect space for us with a living space, kitchen and nice bathroom. The airbnb had everything we needed and more! Thank you, Nina!

Second time staying at this Airbnb. Excellent hosts, conveniently located, and cottage had all the amenities.

Peter's place had everything one could possibly need, and then some. The location was great, bit of a walk to downtown area, but quite doable. The Sea Swirl a few steps away has the best seafood. We loved the view, and very much enjoyed the trains going by. As mentioned in posting, you will hear the other guests from other units, but generally the is not an issue.

Selestria was super kind & supportive! She made us feel welcomed and made herself available for calls if needed. The home was clean and nice looking :)

Great spot for a few days in Montauk. Really close drive to town only about 15 walk into town. Great food cart on property open when the weather is good. Amazing ocean views from most rooms hard to find in the Hamptons.

The place was immaculate and smelled great. By far one of the comfiest beds I have ever had in my times staying in Air BnB's! Really convenient location. Nicole was extremely kind in getting us in!

Great stay in Stony Creek Village with a view of Long Island Sound and short walk to the pier, Stony Creek Market (breakfast & lunch). I used the Library and went to services at the Stony Creek Congregational Church. Overall, a nice experience.

We had a lovely stay at this beautiful home! We actually ended up having pictures taken in the backyard because of how gorgeous the scenery is. Becky was super responsive and friendly. Definitely would love to come back! :)

Hannah (and Corey's!) place was probably the best AirBnB I've ever stayed in. It was clean, well-decorated, spacious and gave us the ability to relax and be productive creatively. It was also the longest I've stayed in an AirBnB (a month) and I'm not sure many other places can pull that off. It truly felt like home and that starts from the top with Hannah. She and her husband and even her parents were so nice when we interacted with them and were accessible immediately if we ever had an inquiry. If you want peace of mind, relaxation and inspiration, you can't find a better place. Thank you again Hannah and family for your hospitality and good energy!

Lisa's apartment is exactly as depicted in the AirBnb listing. It is spacious, clean, comfortable, close to the village of Sag Harbor and down the block from a beautiful private beach. Given the cost of hotels in this area this apartment is an excellent value. While we did not speak or meet during our stay Lisa provided clear directions with regard to finding the home, parking and how to enter and left us her cell phone number in case we needed anything.

Jane was a fantastic host—super friendly and clear with all communication. Her place is perfectly situated between Bridgehampton and Sag Harbor, making it really convenient. The private entrance on the side of her house was a nice touch, and the space was spotless. I also appreciate that Jane clearly put a lot of thought and effort into making the most of the layout, given the space available.

The place was just what I needed, it punches above its weight class, and had the right accommodations. More importantly, the host is super responsive.

Peter was extremely responsive and helpful. Helped with all requests and accommodations. Would recommend and book again. 10/10

We had an amazing stay! Beautiful condo the decor is spotless & the outdoor deck is a huge bonus. Watching the sunset or having coffee in the morning really lade the stay even more relaxing. I cant wait to go back. :)

My family enjoyed their short stay at Camilla’s apartment. The apartment was a beautiful place.

Great spot in a quiet area in Cherry Grove. Has everything you need for a great visit. Easy to get in. Clear instructions. Great value. Gina was very helpful and very responsive.

Kelly was quick to respond to any questions and was very helpful and friendly. We had a great time at this wonderful place!

Upon arriving we were taken with the location, beautiful and ample plantings and attention to detail like a bottle of wine and a variety of snacks to welcome us. The hosts were gracious, warm, gave us privacy, and great tips on where to eat. Cowfish in Hampton Bays is not to be missed. A large and private hot tub, comfortable lounges, and outdoor shower are just some of the amenities. A fire pit with water views was a great spot to unwind at night. The hosts gave us kindling and a lighter, and were very responsive with other asks and recommendations. It’s a great location with ease of access for both the North and South Fork. Would not hesitate to recommend to others.

Had a great stay. Jamie was helpful and responded quickly, and accommodated us kindly. The house is very close to the ferry, which made the trek with luggage very easy. The house is one lot from the ocean, and hot tub on the roof has a great view. The mattress was also really great, sleeping well isn’t usually in the Pines experience but it was a highlight this trip

We stayed for our honeymoon - long weekend and first time Hamptons visitors. Very clean, organized and cozy space with nice decorations. All amenities listed were available. We really enjoyed the hot tub and firepit, very peaceful and private area. You should have a car to get around to restaurants, shops, and other outdoor activities. Lots of areas were walking, bike, and scooter friendly. There were so many beautiful views of the water!! Would stay here again, great value.

We had a great stay! The location is perfect and quiet. House was way better than what we expected. This place is a true heaven! Highly recommended!