Pet-friendly holiday rentals in Wainscott

The house was very clean, well-decorated and cozy. The appliances were all updated and nice to use. We enjoyed staying in the area as it was half way between Sag Harbor and Southampton. Would stay again. Thanks for the hospitality!

Great place for a small family. Short walk to town. Quiet and private backyard for hanging out by the pool. Eric and his team were very responsive to all of our needs. We would stay here again.

Our hosts were amazing. They responded quickly. They were very welcoming to us and provided easy-to-follow instructions. The location was great and the house was lovely. I would definitely stay here again.

Our recent stay at this Sag Harbor was absolutely delightful! The house was charming . We felt at home in the beautifully decorated and its well-equipped. The kitchen had everything we needed to prepare meals, and the living area was perfect for relaxing after a day of exploring. The location was ideal – a peaceful retreat yet just a short drive to the heart of Sag Harbor village with its lovely shops and restaurants. We also appreciated the proximity to the beaches.the pool are is like a mini resort! We will be back for sure.

My friends and I booked Renee’s place for a relaxing getaway weekend. The house was exactly what we needed, clean, private, and full of everything we needed. Renee was responsive and flexible and overall just a wonderful host. We would stay here again in a heartbeat!

My two girlfriends and I stayed at Marianne’s house for a weekend escape, and it was absolutely perfect! The house was clean, cozy, and easy to find. I especially loved the peaceful morning walks to the nearby coffee shop. Marianne was incredibly responsive and offered great recommendations for things to do in the area. Thank you so much, Marianne – we had a wonderful time!

An ideal location in Southampton, Lori’s house is clean, cozy and peaceful; we thoroughly enjoyed spending our New Years there!

cozy , quiet, and far enough from nyc youll feel youre in the countryside. fall asleep to the sound of the ocean. enjoy the morning sunrise with a cup of tea. will be back for sure. accommodates 2

My daughter and I were we out the door early and in the door late every day we stayed. We did use the pool the first day which was so nice! The space was perfect and Stephanie was on point with her communication. Thank you!!

Wendy’s house is immaculate, tastefully decorated, very spacious and extremely comfortable. Her instructions were clear and her responsiveness immediate. We would absolutely consider staying there again.

Not our first and not our last time at Michael’s place. Thank you again for your hospitality and will for sure be staying at your place in the near future.

This was the perfect weekend that my family and I were looking for. Chris is a great host; responsible, responsive, and super friendly. The cabin was absolutely beautiful and clean, with AC and amenities included that made our experience unique. The pool is incredible and everything was provided to have the best time. Honestly, I highly recommend this place for any family or friends looking to spend a quiet and relaxing weekend at this outstanding place. Definitely worth it and I cannot recommend this place enough!!!!

We had the best weekend! The place was safe, clean and easy to find and close to all the local shops. There was no hose to clean off the outside chairs so that we could lounge and the Pool did need some cleaning (the scooper there was broken) but we did what we could! Minor details honestly. All in all I give 5 starts because the host was fantastic and the home was beautiful. Hope to stay there again in the future!!!

Gorgeous house and property that is even better than the photos. Like other reviews have mentioned, the highway noise in the backyard is definitely present, but easy enough to ignore. Really enjoyed our stay and communication was great!

This was such a great stay for our family. The smart TVs were great for my toddler, we were super close to town and Montauk, the kitchen was very useable. The Springs area was new for us but it was such a great vibe. Wish there was an option for daily pool cleaning/maintenance, but not a must have. The pool could also use some work around the perimeter. There’s a lot of dirt and debris built up from the surrounding trees that my son (2 year old) was getting into. Without kids, this is no big deal. Overall the pool was great and we enjoyed the heating and got in everyday. My dog (35 lb labradoodle) was able to get under the deck which was fine, but we just constantly checked for ticks to assure he was okay. No issues there. He loved the huge yard the same way we did.

This was our second time staying at Ron’s place, and it was so great! The location is wonderful, the place is super dog friendly, the beach is perfect location. It’s a cute group of cottages down old Montauk highway, so away from the hustle and bustle but close enough for Ubers and driving! Can’t wait to stay again!

Amy was fantastic from start to finish. The house has four good bedrooms. The bottom floor is very private. Great kitchen and we loved the fact there were cooking basics like olive oil, spices, etc all there.

Great location, comfortable house! Conveniently located near lots of wineries and farm stands and within a quick drive or 20 minute walk to local beaches, this Airbnb is a great home base for a trip to the North Fork. The big fenced in yard was a plus for the dogs (and the kids!). We hope to return soon.

This is the second time we stayed at Kim’s. It was another pleasant experience. Kim is responsive and easy-going. Her home is welcoming and very dog-friendly. We love that Kim has beach access and it is walking distance. The convenience of her home being close to Southampton and Sag Harbor restaurants and shops is a plus. Thanks for having us, Kim. We will be back. xo - Dave, Sasha & Ginger.

Carin’s house was peaceful and relaxing. We stayed a short weekend and was great for what we needed. Large space, enough room to stretch out with our toddler. Beach towels and blankets were a nice touch, and bath robe for me and my little were a fun after beach treat. One thing of note, we are sensitive to dog allergies and some of the bedding did have some traces of dog hair. Just wanted to make sure others might know, I probably should have read the listing more clearly that it’s dog friendly.

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.

Wow, where do I even begin? The photos don’t begin to capture the true beauty of this bay front gem in Southampton’s North Sea community. From the inviting, open-concept design that feels both spacious and cozy, to the serene outdoor retreat surrounded by lush greenery, every corner of this property is a slice of paradise. The views of the bay and sunsets truly take your breath away, making each moment feel magical. Petra is the ultimate host—gracious, thoughtful, and always quick to respond with helpful communication. She ensured our family’s stay was nothing short of perfect. This is definitely a place we’ll be returning to, and we’ll be counting down the days until we can experience this peaceful haven again!

Perfect getaway close to the city. Beach is beautiful! Brooke has the place stocked with everything you'd need. Will definitely be booking again!

We had a wonderful stay at the (Chel)sea. Chelsea herself met us up on arrival to showed us around, and she was super friendly & welcoming. The beds were really comfortable, the sea breeze was relaxing and despite our weather being a bit rainy, the proximity to the water and private beach made this a true retreat! Walkable area, natural surroundings and a lovely restaurant (La Plage) at the end of the road. Kudos to the cleaning staff who left sweet touches throughout. We'd love to stay here again!