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!!

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.

We had the most magical stay at Keely’s place. Her home is beautiful and smelled amazing. Thriving plants, surfaces of wood and stone - a true naturalist’s refuge. The picture windows overlooked gardens bursting with flowers. We meandered from the backyard onto hiking trails through the woods, lounged on the deck in the sun and savored the tranquility. Perhaps the best Airbnb we’ve ever encountered. 10/10

Had a great stay at Lisa’s home! Perfect size for a small family. The streets were a little narrow so we didn’t quite feel comfortable walking the neighborhood, but the surroundings were beautiful and it was very quiet and seemed safe. Lisa’s home was stocked with anything we may have needed, and felt like home away from home. It’s off the beaten path a bit, but there are plenty of restaurants, stores, and places to explore just a short drive away. Lisa was protective and communicative throughout our stay.

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!

Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)

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!

This cottage is tucked back in the woods. We saw many beautiful deer and other wildlife and birds. It’s a bit off the beaten path, not near shops, but suited us very well. Paul, the host was very responsive and friendly. The place was well stocked with personal items and many snacks. Beautiful towels, pillows etc.

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.

The place was really nice and the host was great! Don’t get discouraged if the power goes out during your stay cause apparently that’ll happen 2-4 times a year according to the host. Other than that I highly recommend

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.

Our stay here in Newburgh was lovely! This place was well-stocked, very very clean, fabulously eclectic, and spectacularly spacious! We loved having two restrooms and being so close to the river and to Hudson Taco!! As the Host mentions, do carefully consider how much you care about “neighbor noise.” While I brought slippers to kindly observe the “no shoes in the house” rule, the tenants above us rudely did not. We couldn’t hear voices, but the heavy footsteps kept us awake until 1 o’clock in the morning on a weeknight and woke us up at 6:30 AM on Saturday morning. The dog scampering around or crying and whining loudly every time it was left alone in the house was also hard to bear despite our bringing ear plugs. We would 100% stay again if Sarah would kindly have us. We’re sure to have more considerate neighbors next time. Thank you for creating such a lovely space at an affordable rate.

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.

Will definitely be repeat customers when we come back to CT to see friends and family. The place is exactly as described, spotless and was a home away from home. Elizabeth answered any questions quickly. Thank you for making our first experience with Air Bnb a positive one.

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.

Very chill. Great kitchen and perfect mix of rustic and luxurious. Would happily visit again!