Family-friendly vacation rentals in Highland Falls

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Highland Falls

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guest suite in Montgomery

4.95 out of 5 average rating, 459 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

Guest favorite

Rental unit in Newburgh

4.86 out of 5 average rating, 182 reviews

Riversong on Hudson - Private Full 2nd Floor

This 2nd floor sanctuary is not just a place to stay. Aside from the trains frequently passing nearby, Riversong is a pocket of peace, a window to breathtaking views, and a gateway to a historic city. In this light-filled abode, classic charm meets contemporary comfort. The living area, with a convenient, plush futon, offers space to relax or host an additional guest. Picture windows frame the outdoors, inviting you to gaze on the tranquil river and verdant tapestry of the landscape beyond.

Guest favorite

Rental unit in Highland Falls

4.82 out of 5 average rating, 271 reviews

Stay on Main St Walk to Academy! Free pvt parking

Enjoy this huge private 2 bedroom apartment on Main Street in the heartbeat of Highland Falls and walk just 3 mins to the Military Academy! Unbeatable location for family and friends visiting their cadets! Perfect place to kick back and relax after an Army football game or day of exploration. Centrally located to the best hiking, boating, golf and fishing with an easy drive to Bear Mountain State Park and ZOO, Woodbury Commons Outlet, Storm King Art Center, Eisenhower Theater and LEGOLAND!!

Superhost

Home in Cornwall-on-Hudson

4.92 out of 5 average rating, 153 reviews

Cozy Riverfront Victorian in the Hudson Valley

Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 788 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!

Guest favorite

Home in Highland Falls

4.96 out of 5 average rating, 101 reviews

Enjoy Walking Privileges! WestPoint Farmhouse

Walk to USMA West Point! Stay at an Old Grad mom’s beautiful Farmhouse located right outside Thayer Gate and really enjoy walking privileges!Located in gorgeous Hudson River Valley, this luxurious 1500+ sqft home has central AC and a great backyard for entertaining! Coffee Maker, High Speed WiFi, SMARTTV, 350 Roku channels, sports, Netflix and Amazon Prime! Allergen free environment. NO SMOKING or VAPING, PETS! NO EXCEPTIONS OR LOSS OF DEPOSIT.

Guest favorite

Home in Cornwall-on-Hudson

4.96 out of 5 average rating, 118 reviews

Charming Hudson Valley Home: Minutes to West Point

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

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 728 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.

Guest favorite

Condo in Beacon

4.99 out of 5 average rating, 538 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)!

Guest favorite

Farm stay in Fort Montgomery

4.98 out of 5 average rating, 181 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.

Guest favorite

Home in Highland Falls

4.99 out of 5 average rating, 106 reviews

Cozy 4 Bed 2 Bath Home 1/4 mile from West Point

Split level floor plan featuring 4 spacious, bright bedrooms and 2 full baths. Newly renovated home with large deck for entertaining. Sleeps 10 with room to spare. Quiet end street 1/4 mile from Thayer Hotel at USMA. Walking distance to several restaurants. Amenities include: Satellite TV/WiFi/Washer-Dryer/Dishwasher/Outdoor grill.

Guest favorite

Home in Highland Falls

4.99 out of 5 average rating, 137 reviews

Hudson Valley Farmhouse

Beautifully renovated Farm House with wrap around porch, mature gardens, stone patios and many outdoor entertaining spaces with views of adjoining park and pond. Just 1 mile from West Point main gate; 4 miles from historic Bear Mountain Bridge, Hudson River and the Appalachian Trail.