
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$33,477 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.

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.
KitchenIndoor spacesAccuracy

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!
FamilyIndoor spacesComfort

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.
Indoor spacesFamilyBackyard

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 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, yet still close to all the fun!
FamilyIndoor spacesBackyard

Luxury Cottage with Spectacular Lake Views
Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #P25-0245
Indoor spacesFamilyView

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.
FamilyIndoor spacesComfort

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
Indoor spacesFamilyGrill

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
FamilyKitchenOutdoor spaces

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!
FamilyIndoor spacesAmenities

Private Lake House 1 Hour to NYC & Near Westpoint
Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging
KitchenFamilyAccess

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 spacesWalkability

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.
FamilyKitchenBackyard
Popular amenities for Highland Falls family-friendly rentals
Family-friendly home rentals with a hot tub

Mountain View Retreat
Indoor spacesKitchenParking

Foxglove Farm
Indoor spacesFamilyValue

Magic Red Barn with Heated Salt Pool (opened now)
KitchenIndoor spacesHiking

Accord River House
KitchenFamilyTV

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

Cozy Mountainside Suite - Minutes from Beacon
KitchenFamilyHeating

River & Mtn Views - Jacuzzi - near Metro North
Indoor spacesFamilyTV

Charming Getaway 16mi to West Point!
FamilyIndoor spacesSleep quality
Family- and pet-friendly home rentals

Luxury Lake House Sauna 1h From NYC
Indoor spacesFamilyCleanliness

Waterfront Lake House
KitchenFamilyPets

Hudson Valley Mountaintop Riverview
Indoor spacesKitchenEV charging

Gorgeous Suite w/ Private Entrance
Indoor spacesKitchenHospitality

Unwind in a Bespoke Downtown Studio W Laundry
FamilyIndoor spacesTV

Charming Efficiency
Indoor spacesKitchenLayout

Modern Country Cottage by Bear Mountain
KitchenIndoor spacesGrill

Get Away to "Hygge" Tiny House on 75 Private Acres
KitchenFamilyHospitality
Family-friendly home rentals with a pool

Cozy, Modern Retreat in the Woods of Cold Spring
KitchenIndoor spacesView

Cozy Retreat w/ Pool, Cinema Room & Fire Pit
KitchenFamilyGrill

Private Country Getaway
Indoor spacesKitchenParking

Country Getaway - Close to Hiking & Storm King
Indoor spacesKitchenAccess

Luxury Villa w Lake View & Private Heated Pool
Indoor spacesFamilyHeating

Gorgeous Garrison Gem Sauna, Spa 5 min Cold Spring
KitchenIndoor spacesHospitality

midcentury mod hot tub*walk out trail R2R/Mohonk
KitchenIndoor spacesHospitality

Lakefront/Legoland/HotTub/Heated Pool 1 hr to NYC!
FamilyIndoor spacesBeach
When is the best time to visit Highland Falls?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$60,050 GYD | G$60,468 GYD | G$59,632 GYD | G$59,632 GYD | G$67,164 GYD | G$65,281 GYD | G$57,121 GYD | G$57,748 GYD | G$58,795 GYD | G$62,770 GYD | G$65,281 GYD | G$59,004 GYD |
| Avg. temp | -4°C | -2°C | 2°C | 9°C | 14°C | 19°C | 22°C | 21°C | 17°C | 10°C | 5°C | -1°C |
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