Family-friendly holiday rentals in Westchester County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Westchester County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Englewood
4.94 out of 5 average rating, 158 reviews

Englewood NJ Country Carriage House (15 min NYC)

SarahRating, 5 stars2 weeks ago
Lisa’s place was fun and relaxing for our family. Great place to relax and unwind all while being close to the great areas we visited. Lisa was a great host ❤️
Home in Haverstraw
4.86 out of 5 average rating, 97 reviews

Hudson River House - Ferry to NYC

Séames LiamRating, 5 stars1 month ago
Beautiful location and a beautiful spacious apartment decorated very cozily with a creative and homey feel. Well stocked with kitchen, bathroom and bedding needs. Joan and Jim where a delight to deal with, with clear communication and a genuine appreciation and concern for our needs and satisfaction. coming from an extremely rural and isolated home life I found the industry along the river and area to be of minimal noise and distraction from the natural beauty of the area but suspect most people would barely notice it. The place even came equipped with binoculars witch I used regularly to bird watch into the woodland whilst sitting on the back deck. There are alot of stairs to deal with but it is completely worth the decent/climb to the beautiful locations they serve and the hot tub was always ready for us to use! All-in-all it was an immensely pleasurable stay and I would recommend this home to anyone that likes nature on your doorstep and shops/amenities close at hand.
Superhost
Home in Stamford
4.94 out of 5 average rating, 116 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

DebraRating, 5 stars2 months ago
Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!
Top guest favourite
Flat in Greenwich
4.92 out of 5 average rating, 48 reviews

Safe Quiet Greenwich 2.5 bd+massage+jacuzzi

JulioRating, 5 stars3 weeks ago
My first Airbnb and it did not disappoint! Thanks
Home in North Salem

Equestrians Country Stay and Enchanted Farm House

Family- and pet-friendly home rentals

Guest favourite
Flat in South Salem
4.78 out of 5 average rating, 51 reviews

Cozy Apartment in Horse Country

KimberlyRating, 5 stars3 weeks ago
Very responsive & willing to help. Loved our stay in South Salem. Thank you!
Home in Piermont
4.89 out of 5 average rating, 176 reviews

Hudson River Forest Marsh Cozy Winter Wonderland

ChristineRating, 5 stars19 months ago
My husband and really enjoyed our impromptu weekend getaway at the last minute. Heidi was able to accommodate us the same day and was very quick to respond and help us get setup. The location is beautiful and really special. We’ll definitely be back!
Superhost
Home in Chappaqua
4.87 out of 5 average rating, 78 reviews

Chic and Cozy 2BD 1920's Cottage Retreat

VanessaRating, 5 stars4 weeks ago
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!
Farm stay in Greenwich
4.55 out of 5 average rating, 103 reviews

The Cottage of Laura Ingall's Envy

DirkRating, 5 stars7 months ago
What a pleasure. Jessica has a really special place and it was a perfect location for us. Very private and cozy, we could come and go all we wanted and didn't feel limited. The horses were a great addition and we got to know them. I would definitely stay here again and feel we made a friend.
Guest favourite
Home in Cos Cob
4.98 out of 5 average rating, 58 reviews

Cos Cob CT, 3bdrm, 2bath, with workout room

BarryRating, 5 stars8 months ago
Great home away from home. Made our family feel very comfortable while we were in town for our so sons wedding. We hope to stay again on our next trip. I highly recommend for anyone traveling to the area
Flat in Englewood
4.78 out of 5 average rating, 139 reviews

Cozy Attic Apartment, close to hospital and city

ShantiRating, 5 stars1 week ago
I loved my stay at Sylvia and Daniel's attic apartment. It was perfect for my needs. It was quaint, comfortable, quiet, peaceful, and I felt safe being there alone. I loved the art on the walls, the set up of the space, and the bed was incredibly comfortable. The backyard sitting area was nice too and I appreciate that dogs are welcome. Daniel may be the friendliest host I've met. I will be back!
Apartment in Stamford
4.75 out of 5 average rating, 131 reviews

Chic and Cozy Loft Apartment w/garage parking

IanRating, 5 stars2 months ago
I thoroughly enjoyed the condo! It was well within walking distance to downtown, and the building staff was friendly. Would stay here again.
Home in Mount Vernon
4.59 out of 5 average rating, 93 reviews

Fleetwood Studio apt, Non contact nonsmoking

RichardRating, 5 stars3 months ago
Hugh was very proactive ensuring my check-in went well and everything was to my liking. I recommend staying there.

Family-friendly home rentals with a pool

Home in Philipstown
5 out of 5 average rating, 9 reviews

Arkadia House Mid-century retreat with pool & view

AriRating, 5 stars71 months ago
Dan and Andrew were great hosts and very easy to communicate with. The location was beautiful and the views were amazing. The house was stocked with everything you could possibly need; towels, bedsheets, blankets cookware, a bunch of basic food necessities & more. The pool was refreshing after laying in the sun and watching the sunset from the pool is truly a must when visiting this home. We would love to stay here again and highly recommend to others looking for a gorgeous getaway home.
Guest favourite
Home in Englewood
4.94 out of 5 average rating, 158 reviews

Englewood NJ Country Carriage House (15 min NYC)

SarahRating, 5 stars2 weeks ago
Lisa’s place was fun and relaxing for our family. Great place to relax and unwind all while being close to the great areas we visited. Lisa was a great host ❤️
Home in Yorktown Heights
4.89 out of 5 average rating, 9 reviews

Custom-built Summer Escape with Large Pool

TimothyRating, 5 stars5 months ago
We had an incredible stay at this beautiful home for the holidays! The house is spacious and immaculately decorated, with thoughtful touches that made it feel warm and inviting. The layout was perfect for hosting our family gatherings, with plenty of room for everyone to spread out and relax. The kitchen was fully equipped, making meal prep a breeze, and the cozy living areas were ideal for relaxing.. The quiet suburban setting offered a peaceful retreat, while still being close to everything we needed. We couldn’t have asked for a better place to create lasting holiday memories. Highly recommend!
Home in Rye
4.63 out of 5 average rating, 8 reviews

Colonial Charm · Walk to Town + Housekeeping

AnthonyRating, 5 stars17 months ago
Thank you to Daniel and Lexie for a wonderful stay. Their home is beautifully presented and we felt right at home straight away. The street is charming and Rye has lots to offer families and couples. Daniel was super responsive and helpful with local recommendations and advice. 5 STARS!
Guest favourite
Home in Yorktown Heights
4.91 out of 5 average rating, 154 reviews

Cozy getaway 1 hr from NYC!

ElizabethRating, 5 stars3 weeks ago
Wonderful stay! Impeccably decorated. So clean. Host was extremely responsive. Kids said they wanted to live there permanently! Falling sleep and awakening to the sounds of the nearby stream out my open window - priceless!!

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