Holiday rentals with outdoor seating in Shelter Island Heights

Erica and Janson's place was perfect for our group of eight to attend a wedding in the Hamptons. You cannot get closer to the North Ferry to Shelter Island and there are many restaurant and shopping options within walking distance... the pizza place next door is open late, PORT restaurant (across the street!) is great for waterfront drinks and dinner. While we didn't use it, the LIRR station from Manhattan is also 500 feet from the front door. Ample parking was appreciated and the place was spotless. Thank you Erica and Janson!

Spent a long weekend here with one other couple and had an amazing first trip to the North Fork. Karine's home was beautiful and close to everything we wanted to see, and her recommendations were excellent and super helpful! I hope to come back soon and would absolutely recommend this place to others. Thank you Karine!

Cannot say enough great things about this house. I’ve stayed in many AirBnBs and other home rentals over the years and this was one of my absolute favorites. The house is beautifully updated and was extremely clean. The kitchen and bathrooms are gorgeous and have everything you need. Beds were so comfortable and the room darkening shades are a rare find in a vacation rental. Close to Greenport town and lots of wineries. Backyard was beautifully landscaped and was amazing for our dogs to run around. We will definitely stay here again!

Maura is an amazing host! She is super friendly and helpful and personable. The house was beautiful and very clean and the location was perfect! I would/will be booking it again in the future.

Kristin’s house was perfect!!! It was even more beautiful in person and had absolutely everything we needed to have the best stay at Greenport! Not only was it beautiful, but it was also in the best location, making it easy to get to and from the Main Street and wineries! I traveled with 8 friends and we all said we’d book again without a doubt! Thank you Kristin for an unforgettable stay!

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

our group found this place when planning a trip to Montauk, and while we did make it to Montauk as well, Greenport was also a pleasant surprise. Great community and quaint town! The place was amazing too! clean rooms, very cozy. And a complimentary wine bottle! Highly recommend!

This home exceeded our expectations! The home is seated on a hill that overlooks a little field — we saw deer every night from the huge deck overlooking that field. The most perfect house for a getaway girls trip. We loved the home so much, we all agreed to come back again in the future! Thank you again

We had a great weekend at Nicholas’s place. It was very peaceful in the woods, and we enjoyed using the record player and looking through the books spread throughout the studio. Nicholas was very responsive when I texted with questions and we used his provided recommendations to find breakfast and dinner. We’d definitely stay here again!

It was such a pleasure spending a weekend in Claire’s studio. The studio is very clean and comfortable, and my wife and I particularly appreciated the kitchenette, which allowed us to prepare a dinner one night and make our own pour-over coffee in the morning. We also loved hearing the birds as we woke up in the morning. And the location is terrific—an easy walk to the Southhold town center and a quick drive to other surrounding attractions like Greenport, nearby beaches, and wineries. Highly recommend!

Wonderful and cozy apartment! We were in town for a wedding and needed a clean and safe space to make home base. This was perfect. Would absolutely stay again!

Great venue. Hope to be back next year!

Great place ideally located next to town and the view is amazing. highly recommend in particular for short term stay.

Kevin’s place was great! Kevin was very helpful and responsive. The place was clean, neat & had everything you needed. The view from the living room & bedroom was beautiful & the lake was a great place to go kayaking. Great for groups looking to have a relaxing weekend, in close proximity to the beaches (~25 minutes). Would definitely come & stay again!

The place was perfect. Eli was super friendly and easy to coordinate with. Great views of the water and a solid home base if the weather isn't cooperating. Really enjoyed the weekend there.

Came for college graduation. Shannan’s place was homey, spacious, and clean. Anything you might need is provided. Close to everything by car. Shannan was responsive to all our messages and seemed friendly, although we did not meet her in person. There is a warning in the listing, but I just want to reiterate that the steps are quite steep! Keep this in mind if you have heavy luggage. Overall a great and comfortable stay.

Mark's place was exactly what I was looking for to ring in the New Year in style, comfort and complete relaxation! I was able to start each day with a quiet cup of coffee and then head directly to the beach for a long morning walk (just a short drive away). Montauk Manor is an absolute hidden gem for a winter break and the indoor pool and hot tub are a rare find in the Hamptons. Check-in/out could not have been any easier and the Manor staff are wonderfully welcoming and friendly. There were still a good number of local shops open, including Left Hand Coffee. 100% recommend for all seasons and will eagerly book again!

We loved Montauk - low key, wild and upmarket at the same time. This apartment was perfect, super quiet yet near everything and loved seeing wild deer from the terrace

Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.

Had a wonderful stay with my family. Clean, comfortable, great location. Good communication. Had a little trouble with the front door first day but someone was available quickly to help. A+

Jeff's place has a lot of character and is spacious. The setting is excellent, near the water, with Satterly Landing right down the road. We enjoyed our stay.

Thank you for the stay. Price, location, communication and apartment were all top notch. We had a great week, definitely recommend, hope to be back.

Just had a wonderful stay at Robert’s place! The place was impeccably clean, and Robert was incredibly responsive and friendly throughout our visit. While the manor has a charmingly vintage vibe and could use a bit of modernization, we truly enjoyed our time there. The warmth of the atmosphere made it feel like a home away from home. We recommend for anyone looking for a cozy getaway!

What a perfect place for my girlfriend and I to celebrate her birthday. Michael’s place is beautiful, modern and extremely clean which is an absolute must for me. Also, he was very proactive in communicating and was great to work with. I would highly recommend the place and Michael overall, as a host. It was just a great experience all around and we had a phenomenal weekend in Mystic!