Family-friendly vacation rentals in Highlands

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Highlands

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Montgomery

4.95 out of 5 average rating, 422 reviews

Garden View Guest Cottage

Located under 15 min. to Stewart Airport...1 mile to City Winery , nearby Angry Orchards , 1/2 hour to West Point Charming cottage setting located in the village of Montgomery, NY, Come for the day or stay for a few to take in all this historic area has to offer. Walk to some of the best restaurants in Orange County or simply read a book in the gardens... Truly a great value since it's a true "apartment " like setting..not just a room, with all the conveniences and sleeps up to 6 people

Feb 10 – 17

G$26,936 GYD per night

Guest favorite

Home in Cold Spring

4.95 out of 5 average rating, 152 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, crib and baby monitor, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Dec 14 – 21

G$115,230 GYD per night

Guest favorite

Chalet in Cold Spring

4.89 out of 5 average rating, 371 reviews

Mountain View Retreat

$175 cleaning fee - couples only (1 bed), adjusted after booking if you ask for it. 15 Minutes from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell service), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

Dec 6 – 13

G$154,146 GYD per night

Superhost

Cottage in Putnam Valley

4.9 out of 5 average rating, 215 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Apr 23 – 30

G$83,403 GYD per night

Guest favorite

Apartment in New Paltz

4.96 out of 5 average rating, 346 reviews

Modena Mad House

Our apartment is 6 miles from downtown New Paltz on a quiet and private setting only 1.5 hours from New York City, in the heart of Hudson Valley's Wine Country and apple/peach orchards. 1 bedroom apartment with separate kitchen living room and front porch. Fridge is stocked with eggs, bread, cheese, coffee, wine. We have a large HD screen TV and Roku, but no local cable. 7 miles from Mohonk Preserve and 10 miles from Gunks climbing area, and great Cross-country skiing. Self check-in

Sep 1 – 8

G$27,067 GYD per night

Guest favorite

Home in Cornwall-on-Hudson

4.95 out of 5 average rating, 104 reviews

Charming Hudson Valley Home: Minutes to West Point

**Currently booking for West Point Graduation 2025. 5-night minimum** Located in the Lower Village of Cornwall on Hudson, 5 miles from West Point, 4 miles from Storm King Arts Center and minutes from amazing hiking trails. This charming house offers everything you need for a relaxing getaway. Spacious deck makes it the perfect spot for a relaxing evening outside. The beautiful Hudson Valley and this charming house can't wait to welcome you! **Home does not have a washer/dryer available

Jul 3 – 10

G$95,829 GYD per night

Guest favorite

Guest suite in Cold Spring

4.79 out of 5 average rating, 484 reviews

Cozy getaway in Cold Spring

Sweet studio attached to our house w/updated kitchen & bathroom on a dead-end street backed up to a nature preserve. We have parking for those arriving by car & are a block from the train if coming up from the city. Walking distance to everything (Main St is 2 blocks away!) We welcome all types of folks and your lovely pets as well. We're here for your needs & offer as much contact or privacy as you like! In the summer, an outdoor shower is available to you as well through the backyard.

Mar 18 – 25

G$31,528 GYD per night

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 744 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Jul 16 – 23

G$22,952 GYD per night

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 680 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Apr 12 – 19

G$27,481 GYD per night

Guest favorite

Apartment in Beacon

4.99 out of 5 average rating, 487 reviews

Rustic Spa Retreat

10 minute walk to Main Street (many restaurants, cafes, galleries, etc) 10 minute walk to Mt Beacon TrailHead. (It's not a hotel and not on Main Street: it's in a residential neighborhood) Cozy, small space set up for a couple (or solo traveler) looking for a relaxing short escape from "The Real World". A couple days here really feels likes so much longer (especially if you take a steam and a jacuzzi)!

Oct 5 – 12

G$38,997 GYD per night

Guest favorite

Cabin in Putnam Valley

4.96 out of 5 average rating, 155 reviews

Furthermore Cabin: your mountaintop escape

Our treetop hideaway is filled with plants. Our home is open for you and your loved ones to connect and be cozy together. Well stocked kitchen, stylish vibe, and seasonal access to 2 beaches down the mountain. Enjoy the lake view from hammocks on the double decker decks. 20 minutes to the Hudson Valley's best hiking. 15 minutes from the Taconic Pkwy and Peekskill Metro North.

May 14 – 21

G$75,278 GYD per night

Guest favorite

Farm stay in Fort Montgomery

4.97 out of 5 average rating, 149 reviews

Secluded overlook cottage near West Point

This quaint little house trailer is located on a secluded horse farm in the beautiful Hudson Valley only 50 minutes from NYC and less than 10 minutes from West Pt. Situated on a mountain top, this private little space is a nature lovers paradise. Come, recline on the new outdoor deck, relax by the fire pit and hike/explore the forest trails right out the front door.

Jun 17 – 24

G$52,281 GYD per night