Fitness-friendly holiday rentals in Wainscott

Incredible location! Walking distance to the town. The neighborhood is very quiet and we felt very comfortable all weekend long. Carole and Rich are wondering hosts, and the apartment had everything we needed. We would recommend!!

Joseph is a delight to work with and the place was extraordinary

Brianna was a wonderful host! Our stay there made it an easy engagement weekend for us! She was quick to respond with our questions and let us do a late check out on our last day. Definitely would book with her again!

Had an amazing stay! Cannot wait to come back!

We were very happy with our stay! Great room, cozy and comfortable! The Manor was very nice as well.

This location could not have been more perfect! Driftwood is a prime oceanfront property with all the amenities you need to make your stay fabulous! Special shout outs to Jay who runs the office like a pro, and Santiago who maintains this property with incredible attention to detail. We cannot wait to return! Already looking at dates!!

Loved it! Very clean, easy check in and check out. Beach access a few steps away.

Ildiko was very friendly and proactive. Her place was very clean and in a great location just a few minutes away from downtown Southhampton. She had plenty of linens and towels. The best part were the toys she had which my kids couldn't get enough of! Thank you Ildiko!

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!

My family and I had a wonderful extended vacation at Garrick’s home. The home was beautifully decorated and we felt comfortable immediately. Garrick was extremely responsive and gave great recommendations for restaurants and activities in the area to entertain our kids on the overcast days. We have rented many times in the Hamptons over the past few years and I felt most comfortable at Garrick’s home . The property and the pool/ hot tub were by far the best!

Daniela was a great host! The home is a real home and you feel comfortable as soon as you step in. The kitchen has every item needed to cook. The basement playroom was amazing! The yard is spacious and well decorated. We enjoyed days swimming in the pool and lounging outside. If we had any questions, Daniela was a message away. We would be so happy to stay here again.

We loved the location and felt that it was even nicer than the photos! Would definitely recommend and stay again next year!

Surf Farmhouse is even more beautiful than in the pictures. We couldn’t have asked for a better place to call home for the holidays! The hosts were very friendly and responsive. Thank you for letting us enjoy your home!

This was the PERFECT place to spend a girls weekend. The house was beyond beautiful, the location was great and the hosts were very responsive. Don’t hesitate to book this incredible house.

We really enjoyed our time at this house! Our family of seven was easily accommodated during our stay. The common areas offered plenty of room, and the renovated kitchen was well stocked with everything we needed to cook meals. We loved having a Nespresso coffee maker as well as a Keurig. The mattresses in every room were very comfortable. The numerous outdoor areas were spacious and offered plenty of seating. The pool was enjoyed by all. One thing to note is that this is a beautiful old house, not a hotel. Most of it has been updated but some minor parts do show their age, such as the sliding door going out to the pool which takes some effort to open and close. This did not bother us at all, and I got the sense that the owners will probably update this as well at some point (since most of the house has already been renovated). We would highly recommend this house and a visit to the beautiful Cutchogue area!

This is a great house on Shelter Island. Our family loved the pool and the basement TV room. The host was accommodating and responsive. Highly recommend!