Family-friendly holiday rentals in Highland Falls

Apartment in Cornwall-on-Hudson

A bright bedroom features a spacious bed with crisp linens and a patterned rug. Two windows allow natural light to fill the room, complemented by neutral wall tones. A bedside table holds decorative items, and a potted plant adds a touch of greenery.

4.94 out of 5 average rating, 144 reviews

Quaint Apartment in Cornwall on Hudson

Looking for a weekend getaway? Come experience this centrally-located apartment in the quaint village of Cornwall-on-Hudson. Step outside to find river views, enjoy miles of hiking trails, Hudson River picnics and kayaking that start right up the road. Just minutes to West Point, the Storm King Art Center, Mount Beacon and Woodbury Commons and still in walking distance to shops, restaurants, and parks. We’re excited to make this your favorite place to stay while visiting the Hudson Valley area.

Home in Cornwall-on-Hudson

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.

4.99 out of 5 average rating, 118 reviews

Your West Point Academy Home Away from Home

Make yourselves at home in this lovely, privately-owned residence as you attend West Point Academy events and tour scenic Hudson Valley. Build in 1900 and renovated in 2019, this house combines historic charm (original wood floors) with modern conveniences. The home's location is a twelve-minute drive to West Point's Washington Gate and within walking distance to the restaurants and shops of Cornwall. Enjoy 4th of July fireworks and weekly summer concerts with ease relaxing on the front porch!

Apartment in Highland Falls

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.

4.83 out of 5 average rating, 284 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!

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, 101 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, yet cozy, this house 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 yet still close to all the fun!

A well-maintained front yard features a vibrant array of flowers, including pink and yellow blooms. Neatly trimmed bushes and a white fence enhance the inviting appearance of the farmhouse. The porch is visible, providing a pleasant outdoor space that complements the lush landscaping.

4.97 out of 5 average rating, 118 reviews

Ultimate Walking Access to Thayer Gate USMA

Enjoy the Ultimate Walking Access to Thayer Gate from this Beautiful Farmhouse. Fully immerse yourself in the West Point experience! Hosted by a ‘23 Old Grad Mom, this Beautiful Farmhouse greets you with spacious dining room seating for 10 to gather around the table, fully equipped kitchen with granite countertops for all cooking needs, 75” SmartTV, 350 Roku channels, Cold AC and great backyard for entertaining! Allergen free environment. No smoking or pets. No exceptions or loss of deposit.

Farm stay in Fort Montgomery

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.

4.93 out of 5 average rating, 277 reviews

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.

Apartment in Highland Falls

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, 119 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.

Superhost

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

4.86 out of 5 average rating, 146 reviews

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

All About "Mitzi" 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 2 Internet TVs, WIFI Work area Large backyard, art supplies, games, books Fire pit NEW Community Pool-walking distance Close to West Point, Storm King, the Hudson, Woodbury Mall, hiking, restaurants, bars, shopping No river or mountain view directly from house (per ABnB) BRAND NEW PLUMBING

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, 193 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!

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.

4.99 out of 5 average rating, 117 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

4.78 out of 5 average rating, 151 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.

4.94 out of 5 average rating, 648 reviews

A dining area features a light wood table surrounded by four chairs. A cozy seating arrangement is located nearby, complemented by a bookshelf filled with books and decorative items. Natural light streams through the windows, highlighting the exposed brick wall and wooden beams.

Apartment in Cold Spring

Beautiful loft space

Located in the heart of Cold Spring, NY, this beautiful architect-designed loft space is only 2 blocks away from the Metro North train stop. It features a large single bedroom, a full kitchen, a full dining table and chairs, and a sleeper sofa.

Popular amenities for Highland Falls family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.92 out of 5 average rating, 128 reviews

A spacious living room features a soft, light-colored couch and a small wooden coffee table. A flat-screen TV is mounted on the wall, while decorative shelves display greenery and art. Natural light streams in through windows dressed with sheer curtains.

Home in Newburgh

Lovely home in town of Newburgh

4.94 out of 5 average rating, 412 reviews

Cabin in Wurtsboro

The Water House - Spring Spa on a Cascading Brook

4.9 out of 5 average rating, 265 reviews

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

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

4.82 out of 5 average rating, 122 reviews

Entire Home (private pool), Event Friendly

4.95 out of 5 average rating, 355 reviews

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!

4.99 out of 5 average rating, 197 reviews

The cabin is positioned in a wooded area, featuring a dark exterior and a sloped roof. A spacious patio area is visible, equipped with seating and a fire pit. A hot tub is placed nearby, illuminated by soft lighting along the pathways.

Cabin in Ellenville

Catskills Cabin, Hot Tub, Wood Stove, King Bed

4.95 out of 5 average rating, 417 reviews

The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.

Guesthouse in Beacon

Cozy Mountainside Suite - Minutes from Beacon

4.92 out of 5 average rating, 165 reviews

Home in Beacon

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

Family- and pet-friendly home rentals

4.87 out of 5 average rating, 1,037 reviews

An exterior view of an old milk barn, featuring a wooden door and overgrown greenery surrounding the structure. The rustic charm is highlighted by exposed brick and an angled roof. A few outdoor furniture pieces are positioned nearby, complementing the natural setting.

Farm stay in High Falls

Dave's Milk Barn

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, 181 reviews

Cozy Riverfront Victorian in the Hudson Valley

4.96 out of 5 average rating, 221 reviews

A dining area features a long wooden table set for meals, with plates arranged on woven placemats. To one side, a bar area displays glassware and coffee equipment. Expansive windows frame scenic lake views, allowing natural light to brighten the space.

Cottage in Putnam Valley

Private Lake House 1 Hour to NYC & Near Westpoint

4.98 out of 5 average rating, 123 reviews

A charming cabin is set against a backdrop of trees, featuring a blue exterior and a sloped metal roof. Reflections of the cabin are visible in the calm surface of a nearby pond. A small deck with steps descends into the water, enhancing the outdoor scenery.

Home in Rhinebeck

Slate Cabin - Stylish Country Escape x Rhinebeck

4.94 out of 5 average rating, 142 reviews

A wooden exterior house is surrounded by trees displaying autumn foliage. A pathway of stones leads to the entrance, where a deck with white railings is visible. Lush shrubs and decorative rocks enhance the natural landscaping.

Home in Philipstown

Cozy 3 bedroom house on quiet private road

4.96 out of 5 average rating, 226 reviews

An outdoor area is visible through a large window, featuring a vintage clawfoot bathtub and a wooden stool. A hammock is suspended nearby. Lush greenery surrounds the space, creating a serene atmosphere.

Home in Spring Glen

Creekside cottage on 65 acres of land

4.99 out of 5 average rating, 189 reviews

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 Balmville

Balmville Mid-Century Gem & Work From Home Retreat

4.98 out of 5 average rating, 214 reviews

Two waterfalls cascade over rocky terrain into a flowing body of water. Surrounding greenery includes trees and vegetation that enhance the natural setting. Sunlight illuminates the scene, reflecting off the water's surface, creating a serene environment.

Home in Verbank

The Waterfall House

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 528 reviews

Home in New Paltz

midcentury mod * POOL * walk out trail 2 mohonk

4.88 out of 5 average rating, 205 reviews

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

4.95 out of 5 average rating, 120 reviews

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

Apartment in Wappingers Falls

5 out of 5 average rating, 237 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

4.98 out of 5 average rating, 148 reviews

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

4.95 out of 5 average rating, 159 reviews

A small red cabin is framed by lush greenery, with a welcoming porch featuring two wooden rocking chairs. Natural stone path leads to the entrance, surrounded by a forest of tall trees and soft moss-covered ground.

Cabin in New Paltz

The Little Shelter at Gunks EcoLodge

Guesthouse in Pound Ridge

The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.

4.94 out of 5 average rating, 120 reviews

A Lovely Cottage in the Woods