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.

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

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.

This is one of the most soulful places to stay on Long Island, Greenport, our second visit. A true family gem with laidback vibes and stylish features.

Great location, private and comfortable. Close to wineries and breweries. Very clean and convenient. I highly recommend.

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!

The house was perfect for my family. I loved the convenience of the one-floor layout and way it allows views of the pool and deck from the almost everywhere so we could enjoy it even when the weather didn't cooperate and we couldn't swim. The family /living room was comfortable and great for relaxing or watching a film. The lower level playroom was great fun with ping pong and billiards set up in two areas. We found everything we needed including electric outlets where you need them. The location was great for us and our rides to Montauk and the other towns in the area for museums and restaurants and views. The only thing less than perfect was low water pressure in the master bath sinks and shower, which Abigail said the plumber was addressing. She was extremely responsive and helpful.

We had a lovely stay fro our rainy June weekend. Southold is a quaint town with some excellent local places and fine dining as well. Took a trip to shelter island with the car on the ferry. Went to a cool vintage store in Greenport. Bed and space were super comfy & cozy. Book this spot you won’t be disappointed! Looking forward to visiting again in full summer weather:)

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!

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.

I really enjoyed my stay! I was visiting New Haven with my mother and two kids and the space was perfect for our needs. Everything was smooth from check in to check out - great communication from the host, super clear instructions, and everything was as listed. Great and safe location too!

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!

Great place , nice people , very commucative, place has everything you need , clean , and felt home , definitely will come back again for great experience

Bob, Dawn, and their dog, Cooper were the greatest hosts! We felt welcomed from the moment we got there until the moment we left. The apartment had everything we needed and more, and the shared spaces outside were very serene. I would highly recommend this Airbnb for for anyone wanting a relaxing getaway. We will be back for sure

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!

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 had a great stay at Julie’s place. There was a slight hiccup with check-in times but Julie was very communicative and sorted it out promptly. The place itself was great, beautiful waterfront views and a private beach. The weather wasn’t the best but we still made the most of it. The apartment was compact but big enough for 4 adults.

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

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.

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.