Family-friendly holiday rentals in Highland Falls

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Large Sunny Studio Peaceful Private Baked Goodies

Private high-ceilinged sunny loft studio. Close to West Point, SKAC, Beacon, Hiking, Bear Mt., Wineries, Breweries -Single Traveler Discount Features -Two super comfy queen sized beds. -Heated Jacuzzi bathtub with bath salts. -Coffee/Tea Bar/Snacks -Home Baked Goodies on arrival -Safe. Secure. Private driveway. Parking at door. -Dedicated work desk. WiFi. -Must be 25 years or older. No parties or gatherings. -2 guest maximum -No 3rd party bookings -Overnight stay - not a hang out.

Adorable 2BR steps to WP campus•Free prk•FastWiFi

Just a 3-minute walk from the U.S. Military Academy, this beautifully updated 2-bedroom apartment is the perfect retreat for cadet families and Hudson Valley explorers. Nestled above Main St., you’ll enjoy stunning mountain views, stylish décor, and unbeatable walkability to local restaurants and boutique shops. Inside, spacious, modern interiors and a fully equipped kitchen provide all the comforts of home. With fast Wi-Fi and no cleaning fee, your stay will be both affordable and stress-free!

Cozy West Point Hide Away and Cadet’s Get Away

Newly renovated basement space in a very quiet secluded neighborhood with a full kitchen, full size bathroom, Fast WiFi, Smart TV, Separate parking, walking distance to Hudson River, Main Street, Bear Mountain State Park, West Point Military Academy and several adventurous hiking trails. For those who like to shop we are located only 20 minutes to the Woodbury Commons and only a 45 minute drive to NYC. Also Stuart International Airport is only a short drive from here.

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.

Modern Country Cottage by Bear Mountain

Wake up feeling rejuvenated in a lofted bedroom beneath a wood-paneled ceiling with skylight windows. Descend a spiral staircase into a warm kitchenette for a cup of coffee, then have a seat in an airy living room beside a brass-plated decorative fireplace. Enjoy a picnic or grill on the front lawn and explore the 4 acres of most authentic Hudson Valley landscape.

Bear Mountain, Westpoint, & Hikers Retreat

The Fort @Fort Montgomery, Westpoint/Bear Mountain New to the rental market! This recently renovated 900 Square foot single story home located 5 miles/7 mins from West Point Military Academy and 3 miles/ 3min from Bear Mountain is the ideal spot for friends and family to convene for a weekend visit in the Hudson Valley.

Nestled in Nature

Welcome to the Hudson Valley, just an hour from Midtown! We’re situated a few minutes from Fahnestock State Park, scenic Cold Spring, and a revitalized Peekskill! While these and many more attractions are nearby, the peace and serenity of our house and property are a welcome change of pace from the city.

Beautiful loft space

Located in the heart of Cold Spring, NY, this beautiful architect-designed loft space is only 2 blocks away from the Metro North train stop. It features a large single bedroom, a full kitchen, a full dining table and chairs, and a sleeper sofa.