Vacation rentals in Highland Falls

4.99 out of 5 average rating, 117 reviews

A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.

Cottage in Warwick

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Home in Cornwall-on-Hudson

A two-story white house is framed by lush green trees. The front porch features red rocking chairs and hanging flower baskets. An American flag is displayed on the porch. A pathway leads to the entrance, which is highlighted by white railings and steps.

4.99 out of 5 average rating, 118 reviews

Your West Point Academy Home Away from Home

Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

Apartment in Highland Falls

A spacious living area is furnished with a dark sofa and decorative pillows, complemented by a light wooden coffee table. A large mirror reflects natural light, while floor lamps provide additional illumination. The room features light-colored walls and sleek wooden flooring, enhancing the open feel.

4.83 out of 5 average rating, 284 reviews

Stylish affordable 2BR Steps from Thayer gate+prkg

Welcome to your stylish retreat in the heart of Highland Falls! This beautiful 2-bedroom apartment boasts a wide-open layout framed with breathtaking Mountain View’s just steps from the entrance to the Military Academy. Whether you're here to visit family, explore the Hudson Valley, or simply relax on your own, this perfect location provides the best blend of comfort, convenience, and style. With fast WIFI, private parking and no cleaning fee, your stay will be both affordable and stress-free!

The exterior of the house is surrounded by trees, with a welcoming front porch featuring chairs. A circular stone fire pit area is visible in the yard, complemented by a gravel surface and wooden adirondack chairs. The driveway is paved and leads to the garage.

4.97 out of 5 average rating, 101 reviews

West Point Mountain House

Welcome to West Point! Enjoy early check-in in and late check out at our beautiful mountainside house overlooking the village on its own private hill! Spacious, yet cozy, this house is great for large families or groups of friends coming to explore West Point, Bear Mountain, Storm King, or the Hudson Valley at large. Just 1 hour from NYC and minutes away from restaurants and local attractions. This 3500 Sq Ft home features fun for everyone in a private setting yet still close to all the fun!

A well-maintained front yard features a vibrant array of flowers, including pink and yellow blooms. Neatly trimmed bushes and a white fence enhance the inviting appearance of the farmhouse. The porch is visible, providing a pleasant outdoor space that complements the lush landscaping.

4.97 out of 5 average rating, 118 reviews

Ultimate Walking Access to Thayer Gate USMA

Enjoy the Ultimate Walking Access to Thayer Gate from this Beautiful Farmhouse. Fully immerse yourself in the West Point experience! Hosted by a ‘23 Old Grad Mom, this Beautiful Farmhouse greets you with spacious dining room seating for 10 to gather around the table, fully equipped kitchen with granite countertops for all cooking needs, 75” SmartTV, 350 Roku channels, Cold AC and great backyard for entertaining! Allergen free environment. No smoking or pets. No exceptions or loss of deposit.

Apartment in Cornwall-on-Hudson

A wooden porch leads to a vibrant purple door, framed by light-colored trim. Potted red flowers add color to the entrance, while natural light filters through the nearby trees, highlighting the rustic charm of the space.

4.98 out of 5 average rating, 236 reviews

Charming Efficiency

Newly refurbished efficiency apartment. Full kitchen, new appliances. Comfy space with queen bed and shower in bathroom. Short stroll to coffee bar & all of Cornwall! 3 miles to West Point. Ten minute drive to Storm King, Dia in Beacon, restaurants on the Hudson River. LOTS of hiking options, wine trails and exploring the Hudson Valley. Woodbury Commons is 10 miles for those who prefer shopping! Happy to help with dinner reservations & help to make your stay memorable! Pet friendly.

Apartment in Highland Falls

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.

4.97 out of 5 average rating, 119 reviews

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, 193 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.

4.97 out of 5 average rating, 235 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.

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, 117 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.

Superhost

A well-lit bedroom features a spacious bed adorned with a light gray quilt decorated with blue floral patterns. Nightstands are positioned on either side, each with a small lamp. Natural light filters through a window dressed with light curtains, illuminating the wooden floor.

Apartment in Highland Falls

4.78 out of 5 average rating, 151 reviews

Cozy 1-bedroom retreat minutes from West Point!

Enjoy easy access to everything from this perfectly located home base. Explore the beautiful Hudson Valley, shop the outlets at Woodbury Commons or cheer for your favorite team at Army home games! You will be on a quiet street in the quaint town of Highland Falls the perfect place for work or play.

4.94 out of 5 average rating, 648 reviews

A dining area features a light wood table surrounded by four chairs. A cozy seating arrangement is located nearby, complemented by a bookshelf filled with books and decorative items. Natural light streams through the windows, highlighting the exposed brick wall and wooden beams.

Apartment in Cold Spring

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.

Popular amenities for Highland Falls vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Highland Falls

4.96 out of 5 average rating, 78 reviews

Apartment in Stony Point

Gorgeous Suite w/ Private Entrance

Guest suite in Highland Falls

The exterior of a two-story house is presented against a colorful sunset sky, with hues of pink and orange blending together. A well-maintained lawn extends in front, while steps lead to the entrance, framed by tall trees and utility lines.

5 out of 5 average rating, 62 reviews

Quiet, Cozy, Private Suite ~1/2 mile to West Point

4.98 out of 5 average rating, 55 reviews

The bedroom features a large bed with a white quilt, accented by decorative pillows in blue and yellow. A pink throw blanket is draped over a woven bench at the foot of the bed. Natural light fills the room through a window adorned with floral curtains.

Apartment in Woodbury

Maple Ridge Retreats - Apt B

4.98 out of 5 average rating, 47 reviews

Place to stay in Monroe

A-Frame Modern House w/ Private Pond

An outdoor space features a circular fire pit surrounded by four wooden chairs. The grass is trimmed, and a deck is visible in the background, providing a cozy area for gatherings. Trees are scattered around the yard, contributing to the natural setting.

4.96 out of 5 average rating, 159 reviews

Cozy House 3 Blocks From West Pt

Superhost

4.85 out of 5 average rating, 13 reviews

Delightful Home!

4.94 out of 5 average rating, 33 reviews

A serene outdoor setting features a sparkling swimming pool surrounded by lush greenery. Comfortable seating areas, including deck chairs, are positioned nearby. Hammocks hang between trees, providing a relaxing retreat. Scenic views of the Hudson River and mountains enhance the tranquil atmosphere.

Home in Philipstown

Arkadia House Mid-century retreat with pool & view