Kid-friendly holiday rentals in Lewisboro

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Lewisboro family-friendly rentals

Kid-friendly house rentals

Superhost
Home in Ossining
4.89 out of 5 average rating, 56 reviews

Camped Inn at Sundial Farm -- Tiny House

MonicaRating, 5 stars7 months ago
Hi! The house was cute and convenient for our purposes. We were on a tight schedule so could not be there when the utilities could be explained to us which put us at an extreme disadvantage. It's a cute place to get away. Thanks for your hospitality.
Top guest favourite
Home in West Side
4.99 out of 5 average rating, 167 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

ChristineRating, 5 stars4 days ago
This stay was perfect! Clean and comfy!!
Top guest favourite
Home in Westport
5 out of 5 average rating, 55 reviews

Westport Deco HAUS /5 min to Town /10 min to Beach

AlexandraRating, 5 stars2 weeks ago
great location and loved the backyard
Guest favourite
Home in East Norwalk
5 out of 5 average rating, 68 reviews

Norwalk/Westport Border, Near Beach, w/Pizza Oven

DanaRating, 5 stars6 days ago
This home is well located. There is some street traffic, but once inside you don't really hear it. The kitchen had all the pots, pans, dishes, and glassware we needed. There was plenty of space for the 4 adults and 2 children . The outdoor deck was wonderful for a happy hour cool down after sight seeing and family visits. We all felt right at home. Thank you
Guest favourite
Home in South Salem
4.92 out of 5 average rating, 12 reviews

4 Seasons By The Lake 3 bedroom Luxurious Home

ChrissyRating, 5 stars2 months ago
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.
Guest favourite
Home in Redding
5 out of 5 average rating, 36 reviews

Quiet and Cozy Cottage near NYC with a Pond

LouiseRating, 5 stars3 weeks ago
We loved Erin’s style, her beautiful cottage was comfortable and welcoming from the first. We found all we needed in the kitchen and everything worked well. The home was light and bright and well thought out. The grounds around the house were heavenly, with grassy dappled pathways through the woods and a gorgeous pond beyond the garden, with a river running through. Endless bird song and deer passing by, it was charming and peaceful. I highly recommend it.
Top guest favourite
Home in Bedford
5 out of 5 average rating, 39 reviews

Comfortable Mid-Century on Quiet Country Road

BessRating, 5 stars1 week ago
Adam provided a beautiful home with everything you could ask for to have a lovely stay. The beds were very comfortable, it was spacious and clean. He was responsive and gave clear instructions for check in/out and using the various amenities. I would definitely recommend him as a host!
Guest favourite
Home in Trumbull
4.97 out of 5 average rating, 32 reviews

Cozy studio quiet and safe

GustavoRating, 5 stars2 weeks ago
amazing place to stay at while in CT. close enough by the big areas, while being in a very quite neighborhood. clean house with a cozy vibe to make you feel at home. while small, the space provided was enough for 2 people and really comfortable. host was fast to respond to messages and was extremely kind. overall 10/10 experience and will recommend to anyone looking for a nice place to stay for a good price.

Family-friendly apartment rentals

Guest favourite
Flat in Ossining
4.94 out of 5 average rating, 136 reviews

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

AmaRating, 5 stars5 months ago
I loved the place. It looks just like the pictures, it was clean and she also had games like connect 4 and Jenga which made my stay fun. The place was easy to find, had free parking and the door was easy to open.
Top guest favourite
Flat in Croton-on-Hudson
4.98 out of 5 average rating, 343 reviews

Luxury 2bd⭐Comfort+Style⭐

AndreasRating, 5 stars3 weeks ago
Maria was a great host, super helpful and sweet. Our family really enjoyed staying here!
Guest favourite
Flat in Glenbrook
4.95 out of 5 average rating, 131 reviews

Terra Hillside Suite | 3 Bed 2 Bath | Green Oasis

ColeenRating, 5 stars6 days ago
My Team was in Stamford for two nights to complete a job. The place was absolutely perfect. Clean, easy to find, and convenient to our job site. There was coffee, tea, and spices available to use. I highly recommend this airbnb.
Top guest favourite
Flat in Wall Street
4.98 out of 5 average rating, 136 reviews

"Triplex Historic Beauty" with Seasonal Garden

JenniferRating, 5 stars3 weeks ago
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.
Guest favourite
Flat in Brookfield
4.92 out of 5 average rating, 281 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Jose CarlosRating, 5 stars2 weeks ago
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
Superhost
Flat in Peekskill
4.8 out of 5 average rating, 170 reviews

Little haven by the woods

HowardRating, 5 stars2 days ago
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.
Guest favourite
Flat in Redding
4.94 out of 5 average rating, 485 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

JerelRating, 5 stars1 week ago
This was a great place to stay especially if you love the outdoors . Really loved the set up and all the amenities . Highly recommend for a weekend away. You won’t be disappointed .
Superhost
Flat in Newburgh
4.86 out of 5 average rating, 189 reviews

Special Nest w Private Entrance River View Porches

CynthiaRating, 5 stars3 weeks ago
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.

Family-friendly apartment rentals

Superhost
Apartment in Wooster Square
4.84 out of 5 average rating, 286 reviews

Stunning, Spacious, Spotless. Close to Yale.

DaltonRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Vernon Township
4.88 out of 5 average rating, 118 reviews

Valley Overlook @ Mtn Creek Resort Park & Play

MyahRating, 5 stars2 weeks ago
I had a wonderful stay at this Airbnb in Vernon, New Jersey, right by Mountain Creek. The one-bedroom space was exactly as described in the photos—clean, cozy, and inviting. The accommodations, including the pool and hot tubs, and sauna were fantastic and easily accessible. The host was very responsive to messages, making the whole experience smooth and enjoyable. Highly recommend!
Superhost
Apartment in Bergen-Lafayette
4.93 out of 5 average rating, 187 reviews

Gorgeous Rennovated Apartment

AmandaRating, 5 stars1 week ago
This BnB was awesome! My husband and I visited from out of state for an event and this place was in a perfect location. A short walk from Liberty State Park, it was exactly as described. The place itself was beautiful, and the bed was so comfortable. We would absolutely stay again! (:
Guest favourite
Apartment in Vernon Township
4.95 out of 5 average rating, 191 reviews

Comfy Studio at Mountain Creek Resort

LaurieRating, 5 stars1 week ago
This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!
Guest favourite
Apartment in Vernon Township
4.94 out of 5 average rating, 848 reviews

Appalachian Lodge Top Floor w/views

LaurenRating, 5 stars1 week ago
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.
Top guest favourite
Apartment in Highland Falls
4.96 out of 5 average rating, 107 reviews

Cozy West Point Hide Away and Cadet’s Get Away

GinaRating, 5 stars1 week ago
Great Airbnb! Great Host! Perfect for visiting West Point
Superhost
Apartment in Vernon Township
4.79 out of 5 average rating, 272 reviews

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

SamRating, 5 stars2 weeks ago
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.
Top guest favourite
Apartment in Beacon
4.99 out of 5 average rating, 582 reviews

Rustic Spa Retreat

MelissaRating, 5 stars1 week ago
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!

Quick stats about holiday rentals that are kid-friendly in Lewisboro

  • Total rentals

    50 properties

  • Nightly prices starting at

    $77 SGD before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore