Kid-friendly holiday rentals in Lewisboro

This is our second time renting this beautiful lakeside home and it was absolutely perfect for our girl's weekend. The kitchen was a dream, with all of the appliances and amenities you could need and plenty of room for everyone. The living room had so much seating and the fireplace made everything that much more cozy. All of the bedrooms had very comfortable beds with the best sheets and comforters. I think everyone was impressed with how well they slept. The owner was super easy to communicate with throughout our stay. We can't speak highly enough about this rental. Thank you !

Elizabeth’s place was great and we thoroughly enjoyed our stay! It had everything we needed to be comfy with our toddler and dog, and the neighborhood had all we needed as well (close to the train station, great coffee at Bobo’s and Lange’s deli for breakfast and lunch). Elizabeth made sure we got in okay and was very responsive. Thanks!

This stay was perfect! Clean and comfy!!

great location and loved the backyard

Cozy home, well located to pop into Bedford Village for morning coffee and a casual dinner. Perfect launchpad to spend a weekend exploring. Styled by an interior designer.

Stayed at Klaira’s place for a long weekend while visiting family in the area. The house was clean, spacious, and had all the necessary amenities. We thoroughly enjoyed our stay.

Our family of 5 and pup had the best time on this gorgeous property! The photos do not do the artful design justice, it’s simply stunning and so thoughtful. Our kids swam ever day and loved the pool. We enjoyed Grace Farms, Prospect Movie Thester and a lovely Father’s Day meal at the Inn at Pound Ridge. The kitchen is incredibly well stocked for someone who likes to cook and DoorDash was also easy to use when we didn’t feel like cooking. We will definitely be back! Thank you, RJ and John!

We’ve stayed at Filiz’s place a few times and it’s perfect! Quiet, clean, and easy to get to where we needed to be. We’ll be back!

The apartment was well maintained, beautifully decorated and clean. Apartment was exactly as described with so many personal touches. My husband and I were so happy with our stay, such a homey feel. Dagmara also gave excellent check in instructions and always quickly responded. I would definitely stay again.

These hosts take great care in making sure their guests feel welcome and at home. The apartment is cozy and comfortable. It had everything we needed to relax after a couple of busy days. Their communication is top notch. And I cannot finish without mentioning the thoughtful snacks. That was really above and beyond - and very appreciated.

We had a wonders stay, and could have moved it. Sue was very responsive to our questions. A very nice place to stay private and quiet.

What a beautiful place to stay in the Hudson Valley. The view from the property is just breathtaking. Dan’s place is very clean, open and beautifully furnished. We can’t wait to come back!

Paul was so incredibly kind and good with communication. He gave clear instructions and everything was as expected. Such a wonderful and serene property and area. He provides such intricate details. I had a towel that was so incredible soft and looked brand new, he gave me soaps and a loofah, he provides toothpaste and he ever had jars with hair ties, cotton rounds, qtips, etc.!! Hello, talk about details!! He had a snack bar with yummy options and complimentary wine!! If you are looking for a place in Greenwich look no further! Thank you so much Paul for such an incredible stay! I hope to be back! :)

Great cozy spot to visit family, with easy access to restaurants, shopping, and the highway. The apartment has a private entrance from the main house and has everything one would need for a stay.

Suzette’s place was exactly what we needed. The apartment provided plenty of room, a great bathroom, and a fully stocked kitchen. The outdoor patio was fabulous for us and our dog. The park that was right out the back door was perfect for going for walks. Suzette’s ‘s place is one of the nicest places we’ve stayed and we will definitely be back when in the area. If you have pets and want plenty of space, this is the place for you.

The place was nice and roomy. Very accommodating. Sarah was fantastic at responding to getting us a coffee pot of which the place did not have one. That was so much appreciated. I hope her future guess will appreciate that also.

Great spot and at a really good price. Was visiting for a Yale event and was near enough to feel close without being too close to downtown. The area around the place is also super cute and not one I had explored previously. Huge plus for some good coffee shops nearby and of course Pepe’s. Camila was a great and responsive host. 10/10 would recommend Camila and this spot.

Anthony is the best host I’ve ever had! So friendly, welcoming, and super responsive. He has clearly poured ample love and care into the space—it is immaculate, stylish, well-equipped, and truly an easy Williamsburg oasis!

This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!

I enjoyed my stay here! Gorgeous condo with an absolutely breathtaking view. Decided to stay here for my friends wedding and it couldn’t have been a more perfect spot. Thank you to Paul and family for allowing me to stay at your home.

Great Airbnb! Great Host! Perfect for visiting West Point

It is a great location, with plenty of things to do in the immediate vicinity. The unit was quiet, clean, comfortable, and provided everything I needed for a week long stay. The owner was very responsive to any query, and I did not have any issues with the unit during my stay. I'd work with Henry again for a future stay in Vernon, NJ.

Loved the stay in the apartment! It was beautiful, peaceful and exactly what we needed to have a little time when life takes over. Will for sure be booking the spot again!! The view of NYC was beautiful. Well worth every penny-one of the nicest, cleanest places we’ve stayed so far! The owners are very attentive to your needs- and if you have questions they are answered promptly- couldn’t have asked for better hosts!!🤗 Thanks again for everything.

Dan’s place is cozy, comfortable and just minutes away from Mt. Beacon in one direction and ten minutes away from Main Street in the other direction. The kitchen is stocked with cooking essentials, though there are so many delicious restaurants nearby- the best of both worlds! The bed was extremely comfortable and the jetted bathtub was a huge bonus. I genuinely relaxed there, which is a rarity for me. Thanks so much, Dan!