Vacation rentals in West Point

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.

4.99 out of 5 average rating, 112 reviews

Modern 3BD West Point USMA House w/ HotTub!

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!

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, 112 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 and cozy, this home 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, but still close to all the fun!

A comfortable loveseat is presented in a muted grey fabric, featuring tufted details and two soft pillows. A textured cushion adds a touch of warmth. The background showcases a smooth, light-toned flooring that complements the modern aesthetic of the space.

4.88 out of 5 average rating, 43 reviews

West Point Rest Stop

Just walking distance of public parking in Highland Falls. We are mere minutes away from Thayer Gates and conveniently situated across from the West Point Museum on Main Street. From our location, there are numerous options available for foot travel. Additionally,we are within a short driving distance of numerous local attractions, including Bear Mountain, Legoland, Woodbury Commons, Catskill Resorts Casino, and numerous museums, hiking trails, dining establishments, and shopping opportunity

4.97 out of 5 average rating, 124 reviews

Ultimate Walking Access to Thayer Gate USMA

Stay an extra day on us! Book 4 nights and get the 5th night free at this family friendly beautiful farmhouse. Enjoy the ultimate walking access to Thayer Gate and immerse yourself in the West Point experience. Hosted by a ‘23 Old Grad Mom, our home features a kitchen with granite counters, dining for 10, a 75” SmartTV, fast wifi and a great backyard for entertaining. Relax in cold AC near the Academy. No smoking or pets. No exceptions/loss of deposit. No smoking or pets or loss of deposit.

5.0 out of 5 average rating, 30 reviews

Old Grad House, within Cadet Walking Privileges

Enjoy a premier West Point stay within cadet walking privileges. Just 1 mile to Michie Stadium, a short walk to Buffalo Soldiers, and only 170 strides to Thayer Gate, this is an ideal home base for all things USMA. The Old Grad House is thoughtfully styled with West Point colors, photos, and family memorabilia, blending tradition with comfort. Cozy yet bright, with smart space-saving design. During football season, 4 club-level tickets in the new stands are available separately.

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, 125 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.

The exterior of a historic home is showcased, featuring a covered wrap-around porch adorned with patriotic bunting and seating. The interior displays a modern kitchen with granite countertops and stainless-steel appliances, a cozy living room with a comfortable seating area, and a stylish dining space set for six.

5.0 out of 5 average rating, 105 reviews

Top-Rated West Point 3 Bed 2 Bath Walk to Thayer

Welcome to the West Point Grad Mom House — Whether you’re visiting your Plebe, Yearling, Cow or Firstie our home was designed with West Point families in mind just steps from Thayer Gate. Why families love staying here: • Walk to Thayer Gate, Main Street • Easy access to West Point • Spacious gathering areas • Historic charm combined with modern comfort • Thoughtful touches from a fellow Grad Mom who understands how special these visits are

Superhost

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.

4.93 out of 5 average rating, 177 reviews

Cozy House 3 Blocks From West Pt

Welcome to this thoughtfully remodeled Historic 1890s home, just steps away from West Point's Thayer Gate. The house is conveniently situated right by Thayer Gate (3 blocks) where there are shuttles to all events and destinations. Steps away (1 block) from the restaurants on Main street and the West Point visiting center and Museum (3 blocks). 10 Mins to Bear Mountain State Park 15 Mins to Storm King Art Center 20 Mins to Woodbury Commons

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, 210 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!

Superhost

The living room features a combination of a black sofa and a light gray couch, adorned with red accent pillows. A wooden coffee table is positioned in the center, and light from a nearby window illuminates the space, complemented by a ceiling fan and wall-mounted television.

4.8 out of 5 average rating, 138 reviews

Lovely 3BR Home with parking-Walk to WP Gate!

Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy up in our spacious living room while dinner is cooking in the fully equipped kitchen. The back deck is perfect for morning coffee, unwinding in the evening with a glass of wine or a family BBQ. You will find everything you need for work or play here in the heart of Highland Falls, New York. Looking forward to having you!

The exterior of a two-story house is showcased, featuring a wraparound porch and decorative trim in green and white. Large windows enhance the facade, while a stone pathway leads to the entrance. Dense trees surround the property, adding to its serene setting.

4.9 out of 5 average rating, 90 reviews

Grad owned cozy 5 bd home right outside West Point

Forget your worries in this spacious and serene space. A comforting house very close to West Point and an 8 minute walk to Thayer Gate Near the Main Street strip with family owned businesses and restaurants. Close by the Thayer Hotel in West Point, where they have delicious Sunday brunch! * Window AC is in select rooms

Guesthouse in Highland Falls

4.86 out of 5 average rating, 21 reviews

The Cottage

Quiet neighborhood, walking distance to town and Academy. Perfect for family visiting students. Also a quick getaway from NYC, 1.5hr drive or Metro North station near by. Hiking trails, fishing, kayaking many outdoor activities along the Hudson. Woodbury commons outlets 15min away for shopping enthusiasts.

Popular amenities for West Point vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in West Point

4.98 out of 5 average rating, 58 reviews

The living room features two navy blue sofas positioned across from each other, creating a welcoming conversation area. A glass coffee table is centered on a light-colored carpet. Natural light filters through sheer curtains, highlighting views of the surrounding greenery.

Home in Cornwall

Sunset House: near West Point, Hiking & Woodbury

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.

5.0 out of 5 average rating, 67 reviews

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

A comfortable living area is furnished with a cozy sectional couch and a wooden coffee table. Natural light enters through two windows with blinds. An air conditioning unit is mounted near the floor, and a ceiling fan adds ventilation. A wall-mounted television is positioned above the table.

4.96 out of 5 average rating, 85 reviews

Lovely 2nd FL Apt Walking Distance to West Point!

Superhost

4.81 out of 5 average rating, 21 reviews

Delightful Home!

4.88 out of 5 average rating, 50 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

A two-story house with a gray exterior is flanked by tall trees in the front. The porch features a covered area with columns, and stairs lead up to the entrance. A concrete pathway is visible, alongside a grassy area with shrubs, and a vehicle is parked nearby.

4.89 out of 5 average rating, 98 reviews

Gateway to West Point.

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.

4.92 out of 5 average rating, 132 reviews

Discover Nature’s Glory! Perfect Family Home

An outdoor dining area is present, featuring a large wooden table surrounded by eight grey chairs. A large red umbrella provides shade, while a gas grill is positioned nearby on a concrete surface. Lush greenery is visible in the background, enhancing the space.