Holiday rentals with outdoor seating in Shelter Island

Beautiful house, perfect for a getaway to the north fork. Very close to a beach. Very clean and comfortable. Elizabeth is a great host. Highly recommend.

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

Isabel's home was in a beautiful location with easy accessibility to town and had all the necessities. Home is neat and clean and Isabel was responsive to our questions. Just a heads up.. although the post says air-conditioning it is not central air and we visited at a time when the window units were not in place as yet because the weather had been cool up to that point. We arrived on a warmer day so we could have used it and although there was a ceiling fan in the kitchen and upstairs bedroom there is none I. the downstairs bedroom. perhaps supplying a floor fan would be helpful

We thoroughly enjoyed our short stay. The house was comfortable, clean, well-stocked, and conveniently located. We didn't have enough time to enjoy the backyard but it looked fantastic. Check-in and check-out were easy and straightforward. Would absolutely stay here again.

This was our second time renting Brian's place for a getaway and this stay was as excellent as the last. We love this house so much and Brian could not be a better host. His communication is stupendous; he was always immediately available to respond to any questions we had.

Lovely setting in the woods. We loved the layout, including many windows with beautiful views. Quiet neighborhood that is very walkable. Seeing baby deer in the spring was an unexpected bonus. Spacious bedrooms with extremely comfy beds. Host responded quickly when we had an issue. The private beach is a fantastic feature and easy to access. Check in and check out were super easy.

Our group of 4 had a great stay at Riley’s! Location was super convenient, check in could not have been easier. We loved sitting on the deck outside and making an outdoor fire. Thanks for a great stay!

Dewey’s place is such a dream! Everything is freshly renovated and just feels so crisp, clean, and stylish. You can tell so much love went into the design it’s the perfect mix of modern and cozy. We felt right at home the second we walked in. The kitchen is gorgeous, the bathrooms are spa-like, and every little detail was just so well thought out. Dewey was the sweetest host super responsive and made everything totally seamless. The location is amazing too quiet and peaceful, but still close to all the fun spots (beach, town, restaurants). We didn’t want to leave! Already planning our next trip back. If you’re thinking about booking, do it you’ll love it just as much as we did!

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!

Claudias place might be my favorite air bnb I have stayed at. She has EVERYTHING you could ever think of! The kitchen is stocked with supplies and coffee, which I really appreciated. It was extremely clean and so cozy and felt like your own little space. It is comfortable, private, and a perfect get away from the city. Great for visiting Hamptons if you have a car! Also love her recommendations. I would come back here again and would recommend it without reserve!

I love this place. Perfect but what we were looking for. Walking distance to access beach. Overlooking the pier. Very clean and check in with.

We had a great stay. The apartment is even nicer than the photos can show, especially the high ceilings, and it's an easy walk to anywhere in Greenport. Amanda has provided every amenity you could need, including a full laundry. There's a very nice coffee maker, so don't forget to either bring coffee or K-pods (it takes either). Amanda was very responsive to any questions we had. If you're a breakfast person, Crazy Beans was a great classic diner spot, and we had a great Mexican lunch at Lucharito's.

Sally was super helpful and responsive. Had a wonderful stay!

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!

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 very much enjoyed our stay at the Cliffside for our wedding weekend! Alice was very flexible with us, which we appreciated because getting married is chaotic enough LOL. Would highly recommend staying here. The unit was spotless and had a wonderful view. We could not have asked for a better stay!

Great stay for a quick weekend getaway! Highly recommend as you are right by the beach, Montauk's downtown, and have access to a pool area.

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

Great retreat for a long weekend. Enough space for family of four. Easy access to everything in the Greenport area. Mia was very responsive, and the place was great. We would stay here again!

We really enjoyed staying at Lynn’s place! Very clean and had a great view of the ocean from the deck. Lynn was very responsive and made the experience seamless. We would definitely stay with Lynn again.

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+

Terrific condo, very communicative and friendly host, and easy check in and check out. Would recommend to everyone!