Family-friendly vacation rentals in West Point

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, 159 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.

FamilyIndoor spacesHiking

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, 110 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!

KitchenIndoor spacesDecor

4.97 out of 5 average rating, 123 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 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, 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.

KitchenFamilyGrill

4.85 out of 5 average rating, 368 reviews

A light-filled space features a well-equipped kitchen with modern appliances and a minimalist design. The wooden staircase, adorned with potted plants, leads to a cozy upper area. Natural light streams in through the window, illuminating the warm wooden flooring and vibrant area rug.

Apartment in Newburgh

Unwind in a Bespoke Downtown Studio W Laundry

A bright & creative studio apartment welcomes you! Totally renovated by us for our family, and now available to you. Pros: ♥Automated check in (no waiting!) ♥ Comfy queen sized murphy bed with a real mattress ♥ Open space hang out, work, play, etc ♥Walkable neighborhood ♥Custom design with unique features (hand made tile, Murphy bed, commissioned mural) Cons: ☆Second floor apartment (one flight of stairs) ☆Rooftop not available in late fall/winter ☆ Studio apartment Welcome home!

FamilyKitchenLaundry

Apartment in Cornwall-on-Hudson

A spacious living area is highlighted by a corner sectional sofa and a round marble coffee table. Soft, natural light filters through sheer white curtains, illuminating the warm wood floors. A dining space with a round table and modern chairs is visible in the background.

4.86 out of 5 average rating, 129 reviews

2-Bedroom in COH, near Newburgh & West Point

Two-bedroom apartment located right in the village of Cornwall-on-Hudson. Right next to the fantastic Italian Restaurante Peppitini and right across the street from the historic bandstand, if you're here on a Tuesday night in the summer, you'll likely be able to have a drink and catch a concert from the porch! Conveniently located close to West Point, Storm King Art Center, Newburgh, great hiking, and even Hudson River kayaking! The two bedrooms are roomy and each has a queen bed.

Indoor spacesFamilyHiking

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, 124 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.

KitchenIndoor spacesQuiet

Home in Cornwall-on-Hudson

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.

4.86 out of 5 average rating, 160 reviews

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.

KitchenFamilyGrill

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

FamilyKitchenCleanliness

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, 175 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

KitchenFamilyCleanliness

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.

4.97 out of 5 average rating, 251 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.

FamilyIndoor spacesBreakfast

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, 158 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.

KitchenIndoor spacesPets

4.92 out of 5 average rating, 154 reviews

A mid-century octagonal house is surrounded by lush greenery, featuring large glass windows that offer generous natural light. A wooden deck extends from the entry, framed by a black railing. The serene hilltop location provides a peaceful retreat in nature.

Home in New Windsor

View House

Magnificent views from this fully renovated octagonal, mid-century glass house on secluded hilltop site. Views of and close access to Storm King Art Center, Schunnemunk State Park, Black Rock Forest. 60 mi from Manhattan, Town of Cornwall, NY. Perfect getaway from the city.

Indoor spacesKitchenWalkability

Popular amenities for West Point family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 110 reviews

West Point Mountain House

FamilyKitchenGrill

4.9 out of 5 average rating, 513 reviews

Chalet in Cold Spring

Mountain View Retreat

KitchenFamilyValue

4.9 out of 5 average rating, 276 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

Indoor spacesKitchenNearby

5.0 out of 5 average rating, 104 reviews

Home in New Windsor

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

FamilyKitchenLong stay

4.95 out of 5 average rating, 110 reviews

The exterior of the home is portrayed at dusk, surrounded by trees. A spacious deck with outdoor seating is visible, along with an oversized hot tub lit by soft lights. Large windows reveal an inviting interior, contributing to the serene ambiance.

Villa in Tuxedo Park

Tuxedo Hilltop Retreat with a Large Hot Tub

KitchenIndoor spacesAccess

4.97 out of 5 average rating, 467 reviews

The open living space features a large wooden table at its center, surrounded by chairs. Floor-to-ceiling windows flood the area with natural light, offering views of the outdoors. Recessed lighting and plants accentuate the high ceilings and triangular architecture.

Home in Beacon

River & Mtn Views - Jacuzzi - near Metro North

KitchenIndoor spacesSleep quality

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

4.93 out of 5 average rating, 107 reviews

Charming Getaway 16mi to West Point!

FamilyIndoor spacesCheck-in

4.82 out of 5 average rating, 103 reviews

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

KitchenIndoor spacesOutdoor spaces

Family- and pet-friendly home rentals

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, 190 reviews

Cozy Riverfront Victorian in the Hudson Valley

KitchenIndoor spacesCondition

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, 245 reviews

Charming Efficiency

Indoor spacesKitchenBathroom

4.99 out of 5 average rating, 186 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

Indoor spacesKitchenParking

4.98 out of 5 average rating, 121 reviews

Apartment in Stony Point

Gorgeous Suite w/ Private Entrance

FamilyKitchenParks

4.96 out of 5 average rating, 149 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!

Indoor spacesFamilyTV

4.97 out of 5 average rating, 225 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

FamilyKitchenBackyard

4.99 out of 5 average rating, 204 reviews

A serene view of Walton Lake captures a wooden dock extending into calm waters. The setting sun casts a warm glow over the landscape, reflected in the lake. Lush greenery frames the scene, enhancing the tranquil atmosphere.

Cottage in Monroe

Cozy Lake Cottage

FamilyKitchenAccuracy

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, 123 reviews

Your West Point Academy Home Away from Home

FamilyIndoor spacesHeating

Family-friendly home rentals with a pool

4.84 out of 5 average rating, 695 reviews

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

FamilyKitchenShared spaces

4.97 out of 5 average rating, 178 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

Indoor spacesKitchenGetting around

4.92 out of 5 average rating, 178 reviews

Home in Beacon

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

FamilyIndoor spacesGetting around

4.95 out of 5 average rating, 177 reviews

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

FamilyKitchenLong stay

4.98 out of 5 average rating, 545 reviews

Home in New Paltz

midcentury mod hot tub*walk out trail R2R/Mohonk

FamilyKitchenCheck-in

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.

5.0 out of 5 average rating, 251 reviews

Cozy Charming Apartment in Private House ⭐️⭐️⭐️⭐️⭐️

KitchenFamilyBackyard

4.94 out of 5 average rating, 100 reviews

Cabin in Montgomery

Historic Cabin with Pool and Fire Pit

Indoor spacesFamilyBackyard