Vacation rentals in Highland Falls

Apartment in Cornwall-on-Hudson

A bright bedroom features a spacious bed with crisp linens and a patterned rug. Two windows allow natural light to fill the room, complemented by neutral wall tones. A bedside table holds decorative items, and a potted plant adds a touch of greenery.

4.93 out of 5 average rating, 122 reviews

Quaint Apartment in Cornwall on Hudson

Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.

A contemporary two-story home is presented, featuring a combination of wood and gray siding. Stone steps lead to an inviting entrance, while surrounding greenery provides a natural backdrop. Large windows allow for ample natural light, enhancing the exterior's modern design.

5 out of 5 average rating, 78 reviews

Modern Usma Home, Walk to West Point. Hot Tub!

Our beautiful 3 bed, 2 bath contemporary home sits just 0.4 miles from West Point Military Academy. The house is equipped with super fast internet, work stations in each bedroom, cozy nectar mattresses, a 4-person jacuzzi, and of course, an incredible back yard patio with a BBQ, fire pit and outdoor dining area. Our kitchen is stocked for coffee lovers with 3 different types of machines ( Nespresso, Keurig, and Miele). There are also Samsung Smart TV's in each bedroom along with Sonos speakers.

Apartment in Highland Falls

A cozy bedroom featuring a spacious bed with white linens and a textured green pillow. A small bedside table with a lamp stands next to the bed. A wall clock is mounted above the bed, providing a subtle pop of color.

4.79 out of 5 average rating, 202 reviews

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!

Guest suite in New Windsor

The sleeping area features two spacious beds, each with coordinating linens in calming green tones. Warm light is provided by two bedside lamps, enhancing a cozy ambiance. A decorative ottoman and a circular rug add texture and comfort to the inviting space.

4.96 out of 5 average rating, 241 reviews

Sunny Studio Peaceful Private Affordable + Goodies

Features -Two super comfy queen sized beds. -Heated Jacuzzi bathtub -Coffee/Tea Bar/Snacks -Home Baked Goodies on arrival -Safe. Secure. Private driveway. Parking at door. - Dedicated work desk. Wifi -Single traveler discount - 5 min SKAC -12 min USMA -10 min Woodbury Common -15 min Newburgh Riverfront Restaurants -25 min Beacon -35 min Bethel -Must be 25 years or older. No parties or gatherings. -2 guest maximum (inquire) -No 3rd party bookings -Overnight stay - not a hang out.

An open-concept living area is shown, featuring a comfortable sofa with throw pillows, a wooden coffee table, and dining chairs positioned nearby. The modern kitchen features stainless steel appliances and white cabinetry. Natural light enters through a window, complementing the warm wood flooring.

4.95 out of 5 average rating, 20 reviews

Charming Stay Near West Point

Enjoy a cozy stay just 3 minutes from West Point! This 2-bedroom, 2-bathroom home with three beds is perfect for families or small groups. Conveniently located across from Walgreens and MyTown Supermarket and walking distance to restaurants like Hacienda, dining and essentials are nearby. Relax in the gazebo with lounge chairs after a day of exploring. Whether you’re visiting West Point, hiking nearby trails, or seeking a peaceful retreat, this is the perfect place to stay!

Guesthouse in Cold Spring

A sunlit open space features a light-colored wooden floor and white walls. Two large windows invite natural light, while a patterned area rug adds warmth. A small table and chairs are arranged nearby, creating a versatile area for dining or work.

4.99 out of 5 average rating, 176 reviews

Modern+bright forest escape - near village & train

Modern, efficient, and elegant private flexible garden apt. Guesthouse can be used as a studio apartment, or as a private personal retreat space for art/work/rest/meditation. Hiking trails available right out the door, and just a few minutes walk to Cold Spring's vibrant Main Street and Metro North train station to NYC and beyond. Comfortable bed, all modern amenities. Private patio. Native pollinator gardens and forest surround. Solar orientation brings in natural light.

4.96 out of 5 average rating, 113 reviews

A two-story home is showcased with light-colored siding and vibrant red shutters. The entrance is marked by a white railing and steps leading to the front door. An American flag proudly stands on a flagpole in the front yard, bordered by a white picket fence.

Condo in Highland Falls

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.

An open dining area features a wooden table surrounded by six dark chairs. A stylish light fixture hangs above, and a modern kitchen with white cabinetry and stainless steel appliances is visible in the background. Natural light filters through nearby windows.

4.99 out of 5 average rating, 177 reviews

Spacious, bright 5 bedroom house near West Point

Recently renovated 5 bedroom, 2 bathroom house located 4.3 miles from the Thayer Gate at historic West Point Military Academy. Located in the scenic Hudson Valley near hiking, fishing, Bear Mountain State Park and many historic sites.Woodbury Commons premium outlets are 20 minute drive. The house is comfortable with many upgrades- full oven and microwave, large fridge/freezer, USB ports .Come and see an Army game - and relax here afterwards!

Farm stay in Fort Montgomery

A charming house trailer is shown with white trim and multiple windows, surrounded by trees. An outdoor wooden deck features a grill, purple chairs, and a small pumpkin. Steps lead up to the entrance, offering access to the inviting outdoor space.

4.98 out of 5 average rating, 207 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.

4.99 out of 5 average rating, 207 reviews

A light-colored cottage exterior features large glass doors, surrounded by trees displaying vibrant autumn colors. A stone pathway leads to the entrance, with a lantern and potted plants adding a welcoming touch. A picnic area is visible in the yard, set against the beautiful natural backdrop.

Cottage in Philipstown

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.

The exterior of a split-level home is shown, featuring a mix of brick and siding. A set of wooden stairs leads to a front deck with a patio umbrella. Two small shrubs are planted near the entrance, and a driveway is visible in the foreground.

4.99 out of 5 average rating, 111 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.

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Other great vacation rentals in Highland Falls

Guest suite in Highland Falls

A sweeping view of the Hudson River is framed by lush greenery and colorful flowers in the foreground. Rolling hills rise in the background under a clear blue sky, creating a serene and picturesque landscape.

5 out of 5 average rating, 14 reviews

West Point 1 Bedroom River View Apt within Home

The fully equipped kitchen displays modern appliances, including a microwave and dishwasher, set against light cabinetry. A central island features counter space and extends into the adjacent laundry area, helping to create an open and functional layout. A welcome sign adds a friendly touch.

5 out of 5 average rating, 43 reviews

Highland Falls Home - 1/2 Mile to West Point

The living area features a comfortable gray sofa adorned with decorative pillows and a round coffee table at its center. Light filters in through sheer curtains at the window, illuminating the space. A view into the adjacent bedroom is visible through an open doorway.

Apartment in Highland Falls

4.83 out of 5 average rating, 58 reviews

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

A spacious living room features a large, comfortable beige sectional sofa arranged around a dark coffee table. Natural light filters in through multiple windows, with light drapes providing some coverage. A television is mounted on the wall, accompanied by decorative accents and a small indoor plant.

4.96 out of 5 average rating, 111 reviews

Ultimate Walking Access to Thayer Gate USMA

A modern living room features a cozy sectional sofa arranged around a glass coffee table. A flat-screen TV is mounted above a blue brick fireplace, with large windows allowing ample natural light to fill the space. Decorative pillows and plants add subtle touches of warmth.

5 out of 5 average rating, 8 reviews

Long Dog Inn

5 out of 5 average rating, 3 reviews

Delightful Home!

4.93 out of 5 average rating, 45 reviews

A bright bedroom features a Queen bed with light bedding and an antique desk set against a painted cityscape. Large windows with sheer curtains allow natural light to fill the space, while wooden beams add warmth to the ceiling.

Home in Fort Montgomery

West Point Cottage

A modern, two-story home is set back from the road, surrounded by lush greenery. The driveway leads to a spacious entrance with a covered porch and a seating area. Trees and shrubs frame the property, adding to the tranquil atmosphere.