
Kid-friendly holiday rentals in Highlands
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Highlands
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
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Popular amenities for Highlands family-friendly rentals
Kid-friendly house rentals

Tranquil Tree-House on the beautiful Hudson River
Such an amazing stay with a beautiful view!! Had one of the best memorable day of my life with my girlfriend. All thanks to Roberta!

Sunset House: near West Point, Hiking & Woodbury
Our family stayed here for my son's West Point graduation. This was our second visit and we were thrilled to be back. This house is well taken care of, clean, and relaxing. It's close to the town of Cornwall, grocery stores, etc so you have access to what you need. The hosts are responsive, helpful and welcoming. Highly recommend!

Creekside cottage on 65 acres of land
We had a lovely stay at this remote little cabin home! It feels more like staying at a friend’s house while they are out of town rather than other types of Airbnb rentals. This is someone’s home, with personality, coziness, and a great view! We saw a ton of wildlife, including beavers, deer, and a black bear, so there is plenty of nature small and large.

Spacious, bright 5 bedroom house near West Point
I stayed here with my family and we absolutely loved it. It had everything we needed and more. We like to cook on our trips and the kitchen had everything we needed and more. Best stocked kitchenware I have ever found in all my travel. Host is thoughtful and proactive. Highly recommend

Cozy House 3 Blocks From West Pt
Our stay was exceptional. We were visiting for graduation at West Point and I loved being so near West Point during the action of graduation week. I don’t think you could dream up a better grad week location. The house was well equipped for hosting celebratory lunches/dinners. It also provided easy access to “walking” breaks from family and to laundry etc. I loved the location! Bin was a caring host. It was obvious that he had/has a common sense hosting style. Plenty of parking available. Beds were very comfortable. Baths were lovely. We enjoyed the porch in between the unseasonably cold rain storms. I loved this house! Thank you, Bin!!

Hiking Hideaway on the Ridge
Rosemary and Ed were warm hosts. They had great advice on where to join hiking trails surrounding their property. The space is welcoming, clean and as described. Rosemary kindly offered us some fresh veg from their garden! Would 100% recommend.

West Point Cottage
My partner and I booked Philomena and Derek’s place for Memorial Day wknd to attend a wedding at West Point. It was the perfect location and a cute space. We went to dinner at a restaurant nearby called the Bird and Bottle Inn which was also great.

A nice place to getaway
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!
Family-friendly apartment rentals

Spectacular Cold Spring Views---Walk To Train
Great stay and great hosts. Thank you!!!

Newly Restored 2BR
Great spot! Very clean and lovely light. The railroad tracks into town were so fun to walk and having the water right there was so lovely and peaceful. We really enjoyed our stay! FYI - Apple maps directed us to a building just past his place for some reason but thankfully Graham has photos of the building in the check in process that helped us realize the map’s mistake :)

2Blocks to MainSt/Roundhouse-UnderMtBeacon-PvtApt
Constanza and Bill’s place was everything we could hope for. It was extremely clean and had all the amenities we needed. Constanza was also very responsive and helpful when it came to questions. The location was also very convenient for hiking and dining at local restaurants. We felt right at home and will definitely be back if we’re ever looking to stay in Beacon again :)

Private Country Getaway
We really enjoyed our stay as a family at this location. Everything was clean and comfy with lovely, peaceful surroundings. Since the weather cooperated, we were able to enjoy the gazebo and pool area which our children especially enjoyed. The host was extremely responsive and courteous and also offered some excellent recommendations for restaurants and fun things to do in the area. We will definitely plan to stay here again when we visit the area in the future!

Cozy 2nd floor apartment in Beacon
Great stay! Super clean and tidy. Minimal but has everything you would need. Location couldn't be more perfect!

The RED Door Suite
Easy access to local towns but private and secure. Exactly as described…no surprises! We would stay again when visiting.

Yellow House one bedroom
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.

Charming Apartment in the Heart of Cold Spring
Lovely stay in the peaceful town of Cold Spring. Location is great. Apartment was a bit cold, but that’s to be expected and the provided space heaters worked well. Will definitely stay again when in the area!
Family-friendly apartment rentals

Mtn Creek - Water Park, Bike, Hike, Golf, Legoland
Great, well-equipped condo close to plenty of activities. Michael was super responsive and made check in a breeze.

Comfy Studio at Mountain Creek Resort
This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!

Appalachian Lodge Top Floor w/views
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.

Appalachian Mt. View 1 Bdrm Suite 3rd Flr Balcony
I've been to the Appalachian a few times over the years...this unit was clean, updated and spot on...near the elevator and great view of both the pool area and the mountain.

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

2 Bedroom + Parking Cozy Condo•Mountain Creek•
We really enjoyed a night at the Cozy Condo! Fabiola was very responsive and helpful! The place really was very cozy and clean. It was exactly as listed and pictured. It’s decorated so cheerful and uplifting! Really nice place! Thanks Fabiola!!

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

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna
Kurk's place is updated nicely. Bed is comfy. The tub is amazing! The resort is very nice, the scenery and mountains surrounding it are beautiful, and the condo all made for a relaxing stay!
Quick stats about holiday rentals that are kid-friendly in Highlands
Total rentals
40 properties
Nightly prices starting at
$90 SGD before taxes and fees
Total number of reviews
3.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Fairfield Beach
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- United Nations Headquarters
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art
- Astoria Park
- Minnewaska State Park Preserve