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Family-friendly vacation rentals in Highland Falls

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Highland Falls

  • Total vacation rentals

    Explore 50 vacation rentals in Highland Falls

  • Nightly prices starting at

    Highland Falls vacation rentals start at G$33,468 GYD per night before taxes and fees

  • Verified guest reviews

    Over 2,860 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 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 family-friendly rentals in Highland Falls

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh

Entire Home, Private Indoor Pool

This unique specious and tranquil getaway private home includes an indoor heated swimming pool, hot tub, an outdoor space of 34 acres for you to enjoy nature, work out equipment, movie theater. Complete eat in kitchen, outdoor grill. washer and dryer, three bathrooms. Huge open space basement equipped with LED changing color light. Rooms have Wi-Fi LED light to connect music. The place sleeps 8 guests, in beds. Two additional twin mattresses.16 guests maximum. Hot tub take a while to heat up.

4.81 out of 5 average rating, 136 reviews
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

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!

4.83 out of 5 average rating, 286 reviews
Guest favorite
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.
Home in Highland Falls

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!

4.97 out of 5 average rating, 114 reviews
Top guest favorite
Home in Highland Falls

Ultimate Walking Access to Thayer Gate USMA

Stay extra day on us! Book 4 nights and get the 5th night free at our 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, with 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.

4.97 out of 5 average rating, 126 reviews
Top guest favorite
A circle of bright orange Adirondack chairs surrounds a fire pit, which is highlighted by flickering flames. Lush green grass extends beneath the chairs, complemented by scattered yellow wildflowers. In the background, tall trees create a natural border under a clear blue sky.
Farm stay in Fort Montgomery

Secluded mountain top horse property near W. Point

"Green acres is the place to be, farm living is the life for me!" 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 mins from West Pt. situated on a mountain top. This private little space is a nature lovers paradise. Come, watch the horses from the front deck, enjoy fresh eggs in the morning, relax by the outdoor fire pit, star gaze & hike/explore forest trails right out the front door.

4.94 out of 5 average rating, 294 reviews
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

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.

4.97 out of 5 average rating, 128 reviews
Guest favorite
A two-story house is situated on a quiet residential street, featuring a white exterior with a contrasting brick foundation. The entrance is framed by multiple windows, allowing natural light to illuminate the interior. A well-maintained yard with greenery surrounds the property.
Home in Cornwall-on-Hudson

Eclectic, Sleeps 5, Wsher/Dryer, Parking, Yard, AC

Clean 2-story house on a residential street/safe area Free on-off street parking Eat-in kitchen Dining room Living room-fold out ottoman Free washer-dryer in utility room 2 Internet TVs, WIFI Work area Large backyard, art supplies, games, books Fire pit Community Pool closed again. Close to West Point, Storm King, the Hudson, Woodbury Mall, hiking, restaurants, bars, shopping No river or mountain view directly from house. Airbnb threw that in.

4.87 out of 5 average rating, 166 reviews
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

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

5.0 out of 5 average rating, 106 reviews
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.
Home in Highland Falls

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

4.93 out of 5 average rating, 178 reviews
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

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!

4.99 out of 5 average rating, 214 reviews
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

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

4.96 out of 5 average rating, 142 reviews
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

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.

4.99 out of 5 average rating, 122 reviews

Popular amenities for Highland Falls family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favorite
Chalet in Cold Spring

Mountain View Retreat

4.9 out of 5 average rating, 519 reviews
Guest favorite
Home in New Windsor

Historic Cornwall Farmhouse w/ Sauna & Hot Tub

5.0 out of 5 average rating, 107 reviews
Guest favorite
An outdoor pool area features a stone patio surrounded by vibrant flowers and greenery. Lounge chairs are arranged neatly beside the pool, and a wooden cabana is visible with a stone fireplace, creating a relaxing atmosphere for guests.
Home in Philipstown

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring

4.83 out of 5 average rating, 110 reviews
Top guest favorite
A sunlit seating area features light-colored, oversized chairs and a round coffee table. Large sliding glass doors open to a view of the forest, enhancing the connection to nature. A minimalistic pendant light hangs elegantly above, while a decorative plant adds a touch of greenery.
Home in Cold Spring

Hilltop Hideaway Forest Villa on 13 acres!

4.95 out of 5 average rating, 369 reviews
Superhost
A private hot tub sits on a cement pad, surrounded by greenery and trees. In the background, lounge chairs are arranged in a clearing, adding to the serene outdoor setting.
Home in Newburgh

Charming Getaway 16mi to West Point!

4.93 out of 5 average rating, 110 reviews
Guest favorite
Barn in Katonah

Red Barn/Heated Salt Pool and Cedar Soaking Tub

4.96 out of 5 average rating, 146 reviews
Guest favorite
Home in Beacon

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

4.92 out of 5 average rating, 181 reviews
Guest favorite
The log cabin is set amidst lush greenery and trees, featuring a sloped lawn that leads to the entrance. Solar panels adorn the roof, while diverse plant life and landscaping surround the home, creating a harmonious blend with nature.
Apartment in Philipstown

Foxglove Farm

4.9 out of 5 average rating, 278 reviews

Family- and pet-friendly home rentals

Guest favorite
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.
Home in Cornwall-on-Hudson

Cozy Riverfront Victorian in the Hudson Valley

4.92 out of 5 average rating, 194 reviews
Top guest favorite
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.
Home in Cornwall-on-Hudson

Your West Point Academy Home Away from Home

4.99 out of 5 average rating, 129 reviews
Top guest favorite
A spacious living area features large windows allowing ample natural light. A gray sectional couch is complemented by a mustard yellow chair and a round ottoman. Wooden flooring is contrasted by a blue area rug, adding warmth to the minimalist design.
Home in Newburgh

Balmville Mid-Century Gem & Work From Home Retreat

4.99 out of 5 average rating, 210 reviews
Guest favorite
A Mediterranean style house is showcased against a backdrop of rolling hills and the Hudson River. The exterior features multiple windows, and a stone chimney rises from the roof. The expansive landscape is highlighted by autumn foliage, creating a vibrant setting.
Home in Garrison

Hudson Valley Mountaintop Riverview

4.93 out of 5 average rating, 185 reviews
Top guest favorite
A hammock is suspended between two trees, providing a relaxing spot beside the lake. Vibrant autumn leaves in shades of orange and yellow frame the serene water view, while a wooden dock is visible in the background, inviting guests to enjoy the tranquil setting.
Home in Putnam Valley

Luxury Lake House Sauna 1h From NYC

4.99 out of 5 average rating, 191 reviews
Guest favorite
A spacious living area features a black leather sofa and an orange ottoman, complemented by a large potted palm. Bright light enters through the open door, enhancing the warm wood flooring and inviting atmosphere.
Apartment in Newburgh

Historic Stunner w/WasherDryer, Balcony, 2 bedroom

4.86 out of 5 average rating, 242 reviews
Guest favorite
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

4.94 out of 5 average rating, 144 reviews
Top guest favorite
Apartment in Stony Point

Gorgeous Suite w/ Private Entrance & Farm Friends

4.98 out of 5 average rating, 138 reviews

Family-friendly home rentals with a pool

Top guest favorite
A spacious living area is centered around a stone fireplace, adorned with wood beams. Natural light filters through large glass doors, offering views of the greenery outside. Comfortable couches are positioned invitingly, creating a relaxing atmosphere for guests.
Home in Cold Spring

Cozy, Modern Retreat in the Woods of Cold Spring

4.95 out of 5 average rating, 179 reviews
Guest favorite
An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.
Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

4.95 out of 5 average rating, 137 reviews
Guest favorite
A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.
Apartment in Chester

Private Country Getaway

4.97 out of 5 average rating, 188 reviews
Guest favorite
A spacious living area exhibits warm wooden floors and large windows adorned with decorative curtains. A cozy futon is positioned on a textured rug, complemented by a decorative welcome sign on the wall. A spiral staircase leads to the upper level, enhancing the open layout.
Apartment in Stony Point

E and T Getaway LLC

4.88 out of 5 average rating, 231 reviews
Top guest favorite
A cozy sleeping area features a queen-size bed dressed in a red and black plaid comforter. Two lamps are positioned on either side, providing soft lighting. A small nightstand holds decorative items, while a trunk for storage is located at the foot of the bed.
Loft in Cornwall

Country Getaway - Close to Hiking & Storm King

4.85 out of 5 average rating, 709 reviews
Top guest favorite
A spacious living area features large windows allowing natural light to fill the room. A stone fireplace is prominently placed against a wooden wall. Comfortable seating arrangements include a large sectional sofa, with decorative plants adding a touch of greenery.
Home in Yorktown Heights

Cozy getaway 1 hr from NYC!

4.91 out of 5 average rating, 186 reviews
Guest favorite
A spacious two-story house features a covered porch with white railings, providing a welcoming outdoor area. Lush green grass surrounds the property, and the backdrop includes rolling hills and a clear sky with clouds, emphasizing the serene location near the water.
Villa in Greenwood Lake

Hillside villa with 9-mile lake views

4.97 out of 5 average rating, 108 reviews
Top guest favorite
Home in High Falls

Comfortable & Spacious Country Home - All Seasons

4.98 out of 5 average rating, 124 reviews

When is the best time to visit Highland Falls?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$60,033 GYDG$60,451 GYDG$59,614 GYDG$59,614 GYDG$67,145 GYDG$65,262 GYDG$57,104 GYDG$57,732 GYDG$58,778 GYDG$62,752 GYDG$65,262 GYDG$58,987 GYD
Avg. temp-4°C-2°C2°C9°C14°C19°C22°C21°C17°C10°C5°C-1°C

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