Family-friendly vacation 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, 150 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.

4.86 out of 5 average rating, 215 reviews

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

Our cozy historical 2 bedroom apartment with river views, two porches, and modern upgrades is just what you need for a delightful getaway or focused work-cation. We've preserved historical charms (hardwood floors, historical trim, retro fixtures) while adding in modern amenities (washer/dryer, dishwasher, stylish bathroom, new kitchen, electric car charger, etc!). Less than a mile from the Newburgh-Beacon Ferry launch, which connects you to Metro North Train. Note: Located on the second floor!

4.97 out of 5 average rating, 121 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 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, and a great backyard for entertaining. Relax in cold AC near the Academy. No smoking or pets. No exceptions/loss of deposit. Book your Army getaway today! No smoking or pets or loss of deposit.

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, 120 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!

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, 106 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 & 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 Foot home features fun for everyone in a private setting, yet still close to all the fun!

4.99 out of 5 average rating, 174 reviews

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

Enjoy the lakefront from my charming home! Fish or Kayak from the private dock or relax on the large deck overlooking the water tucked away on the lake. Boats are included for all guests! Heated bathroom floors, massive TV (86in) + ample lake views. We also have a free Tesla Charger (with an adaptor you can use for other EVs). This is a relaxing retreat tucked away in one of New York's most convenient lakefronts from the city. 20 min to Bear Mountain 35 min to West Point 1 hour to NYC

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, 279 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, 121 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.

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, 198 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 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.

4.82 out of 5 average rating, 130 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!

Home in Cornwall-on-Hudson

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.

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

4.93 out of 5 average rating, 319 reviews

An open studio layout features a dining island with black chairs, a cozy couch in the corner, and a spacious bed made with neutral bedding. Decorative walls showcase intricate designs, while numerous pendant lights hang from the ceiling, illuminating the area. Large windows provide natural light.

Guesthouse in Peekskill

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

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

4.95 out of 5 average rating, 428 reviews

Cabin in Wurtsboro

Forest Spa Retreat on Cascading Brook • 90 Min NYC

4.9 out of 5 average rating, 269 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

4.83 out of 5 average rating, 126 reviews

Entire Home (private pool), Event Friendly

4.99 out of 5 average rating, 208 reviews

The modern cabin is set within a forested area, featuring a sloped roof and large windows. A private patio is furnished with a seating area and a hot tub is positioned nearby, surrounded by stone. The natural landscape enhances the serene setting.

Cabin in Ellenville

Catskills Cabin, Hot Tub, Wood Stove, King Bed

Cottage in Greenwood Lake

A spacious outdoor deck is seen, featuring pink lounge chairs and a small black table with a decorative item. A shaded area with a red umbrella provides relief from the sun. Lush greenery and the tranquil lake are visible in the background under a clear blue sky.

4.98 out of 5 average rating, 144 reviews

Secluded Lakeview Escape with Hot Tub

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

5 out of 5 average rating, 159 reviews

Two wooden docks extend into the calm waters of Greenwood Lake, framed by lush trees and houses on the opposite shore. A partially cloudy sky with blue patches creates a serene atmosphere, complementing the peaceful lakefront setting.

Home in Greenwood Lake

Wake up to this view all summer! Lakefront life!

4.92 out of 5 average rating, 170 reviews

Home in Beacon

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

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 1,064 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

4.99 out of 5 average rating, 275 reviews

A serene outdoor seating area features two wooden chairs positioned beside a stone platform. A fire pit with a crackling flame is set in front of the chairs, overlooking a gently flowing creek and lush greenery, creating a tranquil nature retreat.

Cabin in Millrift

Remote Waterfall Cabin at Swiftwater Acres

4.96 out of 5 average rating, 145 reviews

An open-plan living space features a light-colored sectional sofa and a dark leather coffee table. A dining area with a table and four chairs is positioned near highlighted kitchen cabinets. Warm wood flooring complements the neutral walls, enhancing the modern design of the room.

Home in New Windsor

4 Bd Paradise Gorgeous Design Close to All!

4.98 out of 5 average rating, 127 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

4.95 out of 5 average rating, 122 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

4.88 out of 5 average rating, 212 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

4.97 out of 5 average rating, 300 reviews

A charming two-story house features warm wooden siding and multiple red window accents. A welcoming front porch is adorned with lights, complemented by a gently sloped pathway leading up to the entrance, surrounded by lush greenery and seasonal foliage.

Home in New Paltz

Eclectic one-bedroom house

Apartment in Cornwall-on-Hudson

A wooden porch leads to a vibrant purple door, framed by light-colored trim. Potted red flowers add color to the entrance, while natural light filters through the nearby trees, highlighting the rustic charm of the space.

4.98 out of 5 average rating, 239 reviews

Charming Efficiency

Family-friendly home rentals with a pool

4.98 out of 5 average rating, 536 reviews

An in-ground swimming pool is surrounded by lush greenery, offering a serene outdoor escape. Lounge chairs are positioned on the pool deck, inviting relaxation. The area is accented by planters, creating an inviting and enjoyable outdoor space.

Home in New Paltz

midcentury mod * POOL * walk out trail 2 mohonk

Apartment in Wappingers Falls

The image shows a well-kept swimming pool surrounded by a fenced area and lush greenery. Brightly colored flowers in a hanging planter add a touch of color to the foreground. Poolside lounge chairs are arranged on a textured surface, inviting relaxation.

5 out of 5 average rating, 244 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

4.98 out of 5 average rating, 156 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, 162 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

4.97 out of 5 average rating, 215 reviews

A spacious and inviting pool area features a large, unheated swimming pool surrounded by a stone deck. Sun loungers are positioned near the water, and lush greenery provides a natural backdrop, creating a serene outdoor environment.

Guest suite in Holmes

Huge eclectic space w/ private pool. 1.5hr to city

4.96 out of 5 average rating, 171 reviews

Home in New Paltz

New Paltz dog friendly retreat w/ salt water pool

4.96 out of 5 average rating, 301 reviews

A wooden lounge chair is positioned near a serene saltwater pool, surrounded by lush greenery. The pool's clear water reflects the inviting outdoor space, which is complemented by concrete paving and a manicured lawn.

Home in Cottekill

Peace & Privacy - High Falls (hot tub & salt pool)