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.

4.92 out of 5 average rating, 114 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.

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!

Superhost

A modern living area features a brown sofa adorned with textured white pillows. A dining table is visible in the background, accompanied by sleek black chairs. Natural light filters through a window, illuminating the clean, neutral-toned space.

Apartment in Highland Falls

5 out of 5 average rating, 3 reviews

2bd/1bath near West Point in fmr JP Morgan estate!

This comfortably appointed 1st floor apartment is perfect for visits to the nearby legendary West Point Academy and breathtaking Hudson Valley. Whether visiting your cadet, needing a temporary home or exploring the area, we are ready for you! Located minutes away from the historic village of Highland Falls with a supermarket, a pharmacy and places to eat. Park in a private spot and enjoy a restful, clean and comfortable haven for a delightful stay! Morning coffee and a local team on stand by.

A collage showcases the inviting exterior of the home, adorned with bunting and an American flag. Interior images display a cozy living area with comfortable seating, a well-furnished bedroom featuring blue accents, a dining space with a vintage cabinet, and a modern kitchen equipped with stainless-steel appliances.

5 out of 5 average rating, 36 reviews

West Point Home 3 Queen 2 Bath Thayer Gate

Come experience the best of Highland Falls in our beautifully renovated and centrally located West Point-themed home just outside Thayer Gate. Our central location makes us closer to the gate than any hotel in the area. On the main floor, you'll be greeted by our spacious dining room with a table for six, perfect for gathering with friends and family. The fully equipped kitchen comes with all cooking basics, quartz countertops, stainless-steel appliances, and a Keurig coffee bar.

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.

4.93 out of 5 average rating, 15 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, 170 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, 110 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.

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, 199 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, 204 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, 110 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.

The exterior of the home is framed by green grass and colorful landscaping, featuring a stone wall and blooming yellow flowers in the foreground. Tall trees provide shade, while a clear sky with fluffy clouds creates a bright and inviting atmosphere.

4.98 out of 5 average rating, 104 reviews

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.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Highland Falls vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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, 13 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, 41 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

4.82 out of 5 average rating, 56 reviews

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

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, 4 reviews

Long Dog Inn

The interior of the RV features a well-lit space with large windows offering views of the surroundings. A comfortable sofa is paired with a dining table, while overhead cabinets provide storage. The driver's area is visible, showcasing the dashboard and seating.

Camper/RV in Highland Falls

New place to stay

The Sapper Sanctuary

4.93 out of 5 average rating, 42 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

Farm stay in Fort Montgomery

A modern RV is positioned on a wooden deck surrounded by grassy areas. A set of wooden steps leads up to the deck, which features a small table and chairs. Large trees provide shade, enhancing the natural setting.

5 out of 5 average rating, 5 reviews

Camp Foresta, West Point/Bear Mountain

A modern kitchen area is shown, featuring a large wooden dining table with black chairs and sleek bar stools at a kitchen counter. Stylish pendant lights hang above, while a gas range is displayed beside stainless steel appliances. Natural light enters through window treatments.