Holiday 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!

4.88 out of 5 average rating, 43 reviews

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.

Flat in Highland Falls

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.

Home in Cornwall-on-Hudson

The exterior of a historic Gothic Victorian house displays a charming white façade with detailed gables and a covered front porch. Lush green lawns and trees surround the property, while a shaded outdoor seating area under a red umbrella adds to the inviting ambiance.

4.93 out of 5 average rating, 190 reviews

Cozy Riverfront Victorian in the Hudson Valley

Wake up to stunning views of the Hudson River in this huge, immaculately clean, & beautifully designed historic home. Welcome to Sparrow House, our one-of-a-kind 1859 Gothic Victorian in the Hudson Valley. Only 80 minutes from NYC, 19 minutes away from the Beacon stop on the Hudson line/Metro-North, and 13 minutes from the Salisbury Mills/Cornwall Stop on the Port Jervis line/NJ Transit. The house is spacious, has exquisite light, and river and mountain views from nearly every room.

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.

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

Charming, historic 1910 home in Cornwall, NY with breathtaking sunsets, large yard, large living room, patio for BBQ's and outside firepit (when allowed to burn by local authorities). Our home is perfect for a weekend away or vacation with family and friends. Located a short 1-hour drive from New York City and a short distance to many hiking trails and the Hudson River. We love dogs! There are many dog-friendly hikes and a large dog park nearby.

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

Popular amenities for West Point holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in West Point

The exterior of the renovated home is framed by lush, green hedges. A covered front porch features a light blue seating set with two chairs and a small table. Freshly painted siding complements the welcoming entrance, creating an inviting first impression.

4.97 out of 5 average rating, 71 reviews

Highland Falls Home - 1/2 Mile to West Point

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

Superhost

4.81 out of 5 average rating, 21 reviews

Delightful Home!

4.96 out of 5 average rating, 85 reviews

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.

Flat in Highland Falls

Lovely 2nd FL Apt Walking Distance to West Point!

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

4.89 out of 5 average rating, 98 reviews

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.

Flat in Highland Falls

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.