Family-friendly holiday rentals in Putnam County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Putnam County

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

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Guest favourite

Flat

4.82 out of 5 average rating, 272 reviews

Stay on Main St Walk to Academy! Free pvt parking

Enjoy this huge private 2 bedroom apartment on Main Street in the heartbeat of Highland Falls and walk just 3 mins to the Military Academy! Unbeatable location for family and friends visiting their cadets! Perfect place to kick back and relax after an Army football game or day of exploration. Centrally located to the best hiking, boating, golf and fishing with an easy drive to Bear Mountain State Park and ZOO, Woodbury Commons Outlet, Storm King Art Center, Eisenhower Theater and LEGOLAND!!

Guest favourite

Cottage

4.89 out of 5 average rating, 255 reviews

Lakefront Cottage near Hudson Valley

Named in the Top 30 U.S. Lakehouse Rentals by Refinery29 in May'21, this beautiful, secluded cottage on pristine Lake Oscawana has breathtaking views. Escape the city and enjoy the fresh country air! Extra-large great room, cathedral ceilings, loft bedroom, kitchenette, bathroom, fireplace, wall of double-height windows with spectacular lake views. Central AC/heat, hardwood floors, private large deck with BBQ. Dock nestled in a cove where you can swim or paddleboard. Only 1 hour from NYC.

Guest favourite

Chalet

4.9 out of 5 average rating, 416 reviews

Mountain View Retreat

$175 cleaning fee - couples only (1 bed), adjusted after booking if you ask for it. 15 Minutes drive from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

Guest favourite

Guest house

4.94 out of 5 average rating, 385 reviews

Cozy Mountainside Suite - Minutes from Beacon

The Equestrian Suite at Lambs Hill is a private estate with panoramic views overlooking the Hudson River & downtown Beacon. This beautifully-designed luxury suite sits atop a barn home to Icelandic horses & miniature donkeys, & features an outdoor hot tub, gourmet kitchen appliances, & wrap-around decks. 1 mile to Beacon's Main St, 2 miles to Metro North train station & DIA: Beacon. We can host a max of 2 guests & have some dangerous features for kids so guests should be adults only.

Guest favourite

Home

4.94 out of 5 average rating, 163 reviews

Cozy, Modern Retreat in the Woods of Cold Spring

Newly renovated with modern style and amenities yet retaining all of its rustic warmth and charm, our home is perfect for your next get away. Outdoors, enjoy the salt water pool, patio, grill and fire pit in our secluded setting. Indoors we offer a sauna, steam shower, central heat and air, a woodburning fire place, ping pong table, washer and dryer, and a fully loaded kitchen. Located 7 minutes drive from charming Cold Spring and just across the river from West Point.

Guest favourite

Guest suite

4.92 out of 5 average rating, 386 reviews

Creekside Beacon—Go Car-Free!—Steps to Hiking/Main

(Please click the "Show more" button below to expand & read full listing BEFORE booking! You'll see why I ask at end!) RECENTLY RENOVATED! Wake up next to a burbling creek in this immaculately clean full-floor apartment filled with midcentury design and modern tech. Steps to Main St, Roundhouse, and so much hiking. Perfect for a car-free escape. Easy access to Metro-North train, Dia, & quick walk to Mt Beacon hiking. Also near: Storm King, Breakneck Ridge, West Point.

Guest favourite

Home

4.96 out of 5 average rating, 102 reviews

Enjoy Walking Privileges! WestPoint Farmhouse

Walk to USMA West Point! Stay at an Old Grad mom’s beautiful Farmhouse located right outside Thayer Gate and really enjoy walking privileges!Located in gorgeous Hudson River Valley, this luxurious 1500+ sqft home has central AC and a great backyard for entertaining! Coffee Maker, High Speed WiFi, SMARTTV, 350 Roku channels, sports, Netflix and Amazon Prime! Allergen free environment. NO SMOKING or VAPING, PETS! NO EXCEPTIONS OR LOSS OF DEPOSIT.

Guest favourite

Home

4.9 out of 5 average rating, 163 reviews

Beacon 1794 Home 2acres-Walk to Train,MainSt,DIA

Charming preserved second oldest home in Beacon on nearly 2 acres. Large 5 bedroom house with oversized yard with sport court for a group to socialize and chill. Outside seating with lights and grilling. Short walk to train, DIA, hiking Mt. Beacon, Hudson River, Main Street, restaurants, shops, craft beer breweries and wedding venues. Great for family and friends gathering, events at nearby colleges, and company retreats.

Superhost

Home

4.89 out of 5 average rating, 180 reviews

Warm and worderful craftsman style comfort

Our home is in a quiet, family neighborhood, and just a short walk to Beacon's Main Street with all its' cafes, restaurants, specialty shops, galleries and antiquing. This fully renovated Cape Cod style home is perfect for families or groups and has a very large, private, fenced in yard and beautiful garden. Cable TV and WiFi complete your Hudson River experience.

Guest favourite

Flat

4.87 out of 5 average rating, 293 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

Guest favourite

Home

4.99 out of 5 average rating, 106 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.

Guest favourite

Home

4.95 out of 5 average rating, 129 reviews

Family weekend getaway

Two bedroom home located in Beacon. Mt. Views from living room and dining room windows. Close to mt. and Main st. Children welcome. Baby items available pack n play, bouncy seat, swing. Bear Mt and West Point within driving range. Extra charge for pets $100.00. Four adults or families up to 6.