Holiday houses in Highlands

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, 114 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!

ValueFamilyCheck-in

4.89 out of 5 average rating, 359 reviews

The interior of a wooden sauna is shown, featuring warm cedar walls and benches. A stove is located at the center, surrounded by two folding chairs and neatly rolled green towels. A wooden bucket sits in one corner, emphasizing the tranquil spa environment.

Apartment in Cold Spring

HOT Sauna/COLD Plunge- Mountains-Hiking-NYC Trains

Your SPA - Cedar Barrel HOT SAUNA - Outdoor Cozy updated 1814 Cold Spring Village Classic-NATIONAL Historic Register Close to West Point & Beacon Guest Jack's comments "This apartment gave me the feel that I had my own place in a beautiful river town" Mountain Views - Sunny (12+ Windows) 3 Bedroom Modern Garden Apartment (850+SF) Cozy for 1 to 6 #1 Coffees & Teas Walk to Waterfalls, Hiking Trails, River Beaches, NYC trains Restaurants & cafes Outdoor living space in Garden - birds

ValueLocationBackyard

4.97 out of 5 average rating, 103 reviews

A spacious living room is illuminated by natural light through large windows. A comfortable sofa is arranged with accent chairs around a wooden coffee table. A dining area is visible, featuring a round table and chairs. French doors open to a garden view.

Apartment in Cold Spring

Spacious & Cozy Village Getaway

Beautiful sunny home nestled in an historic part of the village at the top of the hill. Relax in a quiet garden surrounding, just a short walk to restaurants, shopping, or many hiking trails. A pergola greets you as you walk into your private patio entrance. This attached two story apartment has two bdrms, 1.5 baths, a fully equipped kitchen, and a gorgeous living room that boasts a gas fireplace. Sip a warm drink while cozying up to the fire, listening to your favorite record on the Victrola!

LocationFamilyCheck-in

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!

ValueLocationOutdoor spaces

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

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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, 178 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

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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, 211 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!

FamilyLocationComfort

4.9 out of 5 average rating, 225 reviews

A comfortable living area features a cozy couch with assorted cushions, positioned near a stone fireplace. Natural light filters through a window, illuminating wooden beams and eclectic decor on the wall shelves. A coffee table and a few chairs complete the inviting space.

Home in Cold Spring

The Foundry House by the Hudson River

The Foundry House is an ivy covered historic brick home, built in 1800. It was used as workers quarters for West Point Foundry and its lumberyard during the Civil War until 1911. It has been beautifully restored into a cozy and comfortable home. It’s located on a quiet street a block away from Main Street, half a block away from the Hudson River and the Bandstand, and a minute walk to Cold Spring Metro North Hudson Line Train Station.

ValueLocationAir conditioning

4.9 out of 5 average rating, 516 reviews

Chalet in Cold Spring

Mountain View Retreat

15 Minutes drive from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

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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.

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.

FamilyLocationCheckout

4.97 out of 5 average rating, 253 reviews

4.97 out of 5 average rating, 227 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.

FamilyValueHot tub

4.98 out of 5 average rating, 122 reviews

A spacious living area features a light-colored sofa with decorative cushions. A wooden coffee table sits in front, accompanied by two stylish dining chairs at a small table. Natural light fills the room through large windows, enhancing the welcoming atmosphere.

Apartment in Cold Spring

Charming Village Base. Walk to Restaurants & Shops

Charming 1 BR apartment in the heart of Cold Spring. Centrally located in walking distance to restaurants and shops as well as hiking trails. About 15 min walk from Cold Spring train station. Ideally located in a Town Home in the village of Cold Spring with a private entrance.

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Popular amenities for Highlands holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Highlands

Superhost

The exterior of a cottage is presented, featuring a gravel driveway and a single garage. Surrounding trees showcase autumn foliage while a small wooden deck is visible above the garage. The mountains can be seen in the distance beneath a partly cloudy sky.

Home in Philipstown

Bear Mtn Haus near hiking trails

FamilyLocationLong stay

4.86 out of 5 average rating, 140 reviews

4.94 out of 5 average rating, 138 reviews

A lakeside retreat is showcased, featuring a rustic exterior with dark wood accents. Adirondack chairs are arranged near the water's edge, alongside colorful kayaks resting on the peaceful lake. Lush greenery surrounds the property, reflecting in the calm water.

Home in Putnam Valley

Waterfront Lake House

FamilyLocationKitchen

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

ValueLocationAccess

Guesthouse in Highland Falls

The Cottage

ValueLocationNearby

4.83 out of 5 average rating, 23 reviews

4.98 out of 5 average rating, 80 reviews

A spacious outdoor deck is surrounded by trees, featuring four Adirondack chairs arranged around a central fire pit. Natural light filters through the foliage, enhancing the peaceful outdoor setting, perfect for relaxation or gathering.

Cabin in Cornwall

Storm King Forest Retreat

FamilyLocationCheck-in

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

FamilyLocationView

Apartment in Highland Falls

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.

West Point Rest Stop

FamilyLocationCleanliness

4.88 out of 5 average rating, 43 reviews