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Vacation rentals in Highland Falls

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Quick stats about vacation rentals in Highland Falls

  • Total vacation rentals

    Explore 60 vacation rentals in Highland Falls

  • Nightly prices starting at

    Highland Falls vacation rentals start at G$10,449 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,690 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Highland Falls vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Highland Falls rentals

  • 4.9 Average rating

    Highland Falls stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Highland Falls

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Home in Highland Falls
4.99 out of 5 average rating, 103 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!

Guest favorite
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.
Apartment in Highland Falls
4.83 out of 5 average rating, 285 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!

Top guest favorite
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.
Guest suite in Highland Falls
5 out of 5 average rating, 65 reviews

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

The neighborhood is so quiet w/ beautiful views everywhere you look. It's a private suite, w/ private entrance & bathroom, microwave, toaster oven, mini-fridge, & of course, a coffee maker! Extra living space w/ a couch, desk & smart TV. Work out in the morning or watch TV at night. Only ~1/2 mile to West Point, so Main Street (food/drink) & Thayer Gate are in walking distance. Perfect for visiting anyone or attending an event at West Point. Quaint towns, restaurants, hiking in all directions

Top guest favorite
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.
Apartment in Highland Falls
4.96 out of 5 average rating, 84 reviews

Lovely 2nd FL Apt Walking Distance to West Point!

Welcome To The Heart Of West Point. Beautifully Furnished Apartment. Located Steps Away from West Point. Walking Distance to Restaurants, & The Best Landmarks The Town Has To Offer. We Are Minutes Away From Hiking,Swimming, Fishing, & Much More! We are Ideally Located Near Bear Mountain State Park, Woodbury Commons & More! Apartment Includes 2 Full Size Bed, 1 Roll out Twin Bed. Comfortable Couches, Smart Tv, Wifi, & Much More. NO Parties. Family Living on 1st Floor Apartment.

Top guest favorite
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.
Apartment in Highland Falls
4.97 out of 5 average rating, 122 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.

Top guest favorite
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.
Home in Highland Falls
5 out of 5 average rating, 97 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

Top guest favorite
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.
Home in Highland Falls
4.99 out of 5 average rating, 201 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!

Top guest favorite
A charming blue house features a welcoming front porch with steps leading up to the entrance. White shutters adorn the windows, and flower boxes add color. A flag is displayed in front, with a well-maintained lawn and greenery surrounding the property.
Home in Cornwall-on-Hudson
4.96 out of 5 average rating, 140 reviews

Charming Hudson Valley Home: Minutes to West Point

Located in the Lower Village of Cornwall on Hudson, 5 miles from West Point, 4 miles from Storm King Arts Center and minutes from amazing hiking trails. This charming house offers everything you need for a relaxing getaway. Spacious deck makes it the perfect spot for a relaxing evening outside. The beautiful Hudson Valley and this charming house can't wait to welcome you! **Home does not have a washer/dryer available

Top guest favorite
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.
Farm stay in Fort Montgomery
4.97 out of 5 average rating, 245 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.

Top guest favorite
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.
Home in Highland Falls
4.99 out of 5 average rating, 120 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
4.77 out of 5 average rating, 156 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.

Superhost
Home in Highland Falls
4.88 out of 5 average rating, 16 reviews

Delightful Home!

Experience a thrilling gateway from the bustling energy of New York City in this delightful home! Centrally-located, just a short 5-minutes walk to West Point Military Academy and Thayer, and a mere 5.2 miles to the breathtaking Bear Mountain State Park. Adventures await right at your doorstep!

Popular amenities for Highland Falls vacation rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great vacation rentals in Highland Falls

Guest favorite
Home in Highland Falls
5 out of 5 average rating, 5 reviews

Highland Falls Home away from Home. Walk to Thayer

Guest favorite
Home in Highland Falls
5 out of 5 average rating, 5 reviews

Rockbound Escape

Top guest favorite
Home in Highland Falls
5 out of 5 average rating, 28 reviews

Old Grad House, within Cadet Walking Privileges

Guest favorite
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.
Home in Highland Falls
4.95 out of 5 average rating, 168 reviews

Cozy House 3 Blocks From West Pt

Top guest favorite
A round wooden dining table is set for four, surrounded by modern chairs. Sunlight streams through the large windows, illuminating the polished wooden floor. A radiant light fixture hangs from the ceiling, and a stylish cabinet displays decorative elements and a small vase with flowers.
Apartment in Highland Falls
5 out of 5 average rating, 53 reviews

West Point Apartment/Highland Falls NY

Top guest favorite
A spacious living area features an elegant chandelier hanging from a wooden beam ceiling. A white chaise lounge and a blue armchair are positioned around a wooden coffee table. Warm light enters through windows, illuminating the colorful area rug that covers the hardwood floor.
Home in Highland Falls
4.97 out of 5 average rating, 67 reviews

West Point Hudson Valley Getaway

Guest favorite
Guesthouse in Highland Falls
4.88 out of 5 average rating, 16 reviews

The Cottage

Guest favorite
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.
Apartment in Highland Falls
4.86 out of 5 average rating, 36 reviews

West Point Rest Stop

When is the best time to visit Highland Falls?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$56,217 GYDG$56,217 GYDG$45,977 GYDG$52,247 GYDG$56,844 GYDG$58,725 GYDG$53,291 GYDG$54,127 GYDG$53,500 GYDG$58,307 GYDG$62,696 GYDG$55,172 GYD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

Frequently Asked Questions

  • What are the best places to stay in Highland Falls?

    Stays around Highland Falls village allow you to explore charming streets, local eateries, and nearby nature. Homes near the riverside and in quiet residential areas are often recommended for both relaxation and accessibility.

  • What are the best things to do in Highland Falls with kids?

    Families often explore parks and riverside picnic spots or visit local playgrounds. Nature walks, seasonal community events, and nearby educational attractions create opportunities for fun and learning.

  • What are some of the best things to do in Highland Falls?

    Explore the scenic Hudson River waterfront and enjoy local shops around the village. Highland Falls has hiking trails, historic sites, and easy access to outdoor adventure and nearby cultural spots.

  • How is the weather in Highland Falls?

    Highland Falls has cold winters around 16–35°F (-9–1°C), with snow likely, and warm summers near 59–82°F (15–28°C). Spring and fall bring mild, changeable weather, often paired with colorful foliage and outdoor activity.

  • When is the best time to visit Highland Falls?

    Late spring and autumn are often recommended, when mild weather and colorful foliage make outdoor activities popular. Summer attracts visitors for community events and riverside gatherings, while winter brings a quieter pace and the possibility of snow.

  • What are the best places to visit in Highland Falls?

    Highland Falls has a lively village center, scenic riverfront areas, and is near the United States Military Academy campus, which often draws history enthusiasts. Local parks and historic markers highlight the region's stories and natural charm.

  • What are some hiking trails in Highland Falls?

    Highland Falls has woodland trails and riverside paths ideal for hiking and nature walks. Local parks and preserves provide trails for a range of ability levels, with seasonal views of the river and hills.

  • What are some family activities we can do in Highland Falls?

    Families frequently explore playgrounds, hike gentle trails, and participate in local arts workshops. Seasonal events and riverside picnics make Highland Falls a welcoming spot for all ages.

  • What are some of the best day trip ideas from Highland Falls?

    Explore arts and gardens in surrounding towns, visit nature preserves, or discover historic sites in the Hudson Valley. The area around Highland Falls frequently draws visitors for outdoor activities and cultural experiences.

  • Are there any pet friendly accommodations available in Highland Falls?

    Many vacation rentals in Highland Falls welcome pets, especially in residential areas near parks and walking paths. Some hosts provide extra amenities for pets, such as a fenced yard or pet bowls.

  • What are some local tips for visiting Highland Falls?

    Locals suggest exploring the village early to enjoy peaceful streets and fresh bakery treats. If hiking, check trail conditions and bring bug spray; autumn colors around Highland Falls are frequently suggested for photography.

  • What is Highland Falls known for?

    Highland Falls is known for its riverside scenery, historic connection to the United States Military Academy, and access to hiking in nearby hills. The village atmosphere and local events contribute to its distinct character.

  • What are the best hidden gems to explore in Highland Falls?

    Wander lesser-known woodland trails and discover tranquil spots along the riverbanks. Small galleries or historic plaques around the village often share stories of the area’s past and local artists.

  • What are the best foods to try in Highland Falls?

    Explore locally rooted flavors, including American classics, fresh baked goods, and seasonal farm produce. The area is known for its casual cafes, family diners, and small eateries serving diverse cuisine.

  • What should I bring for a trip to Highland Falls?

    Pack comfortable walking shoes, layered clothing for changing temperatures, and a rain jacket. A reusable water bottle and sunscreen are helpful for outdoor activities, especially during warmer months.

  • What is the nightlife in Highland Falls like?

    Nightlife in Highland Falls has a relaxed vibe, centering on local pubs, casual eateries, and occasional live performances. Evening strolls by the river and nearby taverns create a warm, welcoming atmosphere.

  • What are the most popular events or festivals in Highland Falls?

    Highland Falls features community celebrations, summer outdoor concerts, and seasonal festivals often tied to national holidays like Memorial Day or Independence Day. Local fairs and arts events in late spring and early fall draw both residents and visitors.

  • Are there family friendly vacation rentals in Highland Falls?

    Highland Falls has a variety of vacation rentals suitable for families, including spacious homes and apartments. Many accommodations feature amenities like kitchens, extra bedrooms, and easy access to parks and local attractions.

Destinations to explore

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