Family-friendly vacation rentals in Woodbury

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Top-rated family-friendly rentals in Woodbury

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

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Guest favorite

An open dining area features large floor-to-ceiling windows, allowing natural light to fill the space. A long wooden dining table is centered, surrounded by wooden benches. Sheer curtains softly frame the windows, enhancing the connection to the outdoors.

Chalet in Tafton

4.86 out of 5 average rating, 132 reviews

Pocono Chalet~HeatedPool~Sauna~Firepits~Fireplaces

This is a one of a kind LINDAL CEDAR HOME, with an open layout, 16 foot Cathedral ceilings with floor to ceiling windows. Perfect getaway for family outings or friends getting out of the city. Following attractions are nearby: Lakes Wallenpaupack Promised Land State Park Skytop Camelback Ski/tube Kalahari Indoor Water Park Mt. Airy Casino NO PROMS NO FRATS POOL opens mid April and closes mid Nov. All guests are required to accept host's lease agreement prior to check in. Pets need approval

Guest favorite

Aerial view of a spacious property featuring a winding driveway, lush tree cover, and a large farmhouse. Nearby garden plots and additional structures are visible, surrounded by greenery. The landscape presents a peaceful rural setting, ideal for outdoor activities.

Farm stay in Blairstown

4.85 out of 5 average rating, 130 reviews

Cozy LakeView Farm near NYC/Rt.80 & Del. Water Gap

Enjoy Fresh Air & Spacious Views on your retreat w/ a Private Lake, Trails, Fields & Streams throughout. Beauty and Wildlife abounds. Spread out in an open layout 2BR apartment on the garden level. Guidebook for Seasonal Fun! Enjoy the countryside w/no traffic. *Close 2 NYC/Rt 80 thru a Quaint Moravian VIL. Appalachian Trail access. *Animal Tour w/Petting incl. Great local Farms/Markets w/Fresh Food. Alpaca & Wolf Preserve nearby. Hiking nearby. Farm Store soon.*3-day min Holidays. 1 dog<40pd.

Superhost

A two-story home is set amidst trees, featuring a combination of red wood paneling and brick. A large front deck with a staircase leads up to the entrance. Multiple windows offer views of the outdoors, with an American flag displayed prominently.

Cabin in Albrightsville

4.91 out of 5 average rating, 341 reviews

Value! Sleeps 10 Pp+2 Ch Most week nights $99+Fee

Pet friendly Pocono Mountain home located moments away from all major attractions. Skiing, hiking, paintball, water-parks and golf are all within a 10 minute drive. The Towamensing Trails community has an abundance of amenities including a lake with a beach, a pool, boat rentals, fishing, and an arcade for kids. You'll love our open floor plan and decorations boasting a wood burning stove for cold nights and a large deck for warm days. Excellent for families, groups, and romantic getaways.

Top guest favorite

An enclosed porch features two metal-framed chairs with cushions, positioned near a small table. A decorative rug with vibrant floral patterns covers the floor. A potted plant and a lantern add to the decor, with sunlight streaming through the windows overlooking the water.

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favorite

The living room features light green walls with large windows allowing natural light to fill the space. A patterned sofa and two armchairs offer seating. A coffee table sits on a layered area rug, while a corner with a small table and a chair adds functionality.

Home in Athens

4.84 out of 5 average rating, 170 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favorite

An arcade gaming console is positioned against a wooden wall, featuring a bright screen displaying a classic game interface. A child is seated in front of the console, focused on gameplay, while an adult stands nearby, both enjoying a fun moment together.

Home in Bushkill

4.93 out of 5 average rating, 138 reviews

Lakefront, Hot Tub, Pool, Gameroom, Pickleball

Olibear is your perfect spring retreat—ideal for couples, families, or anyone looking for a lakefront getaway. Tucked by the lake, our cozy home welcomes you with the Pocono scenery waking up around it. Just 5 minutes from Bushkill Falls, come explore the fresh spring scenery or relax by the indoor community pool, open weekends 12-4 PM. Hop in the private hot tub, grab a kayak, stroll the trails, or kick back by the firepit under the spring sky. Come claim your spring escape now!

Guest favorite

A collage displays different areas of the Harry Potter-inspired vacation home. A cedar barrel sauna appears alongside a cozy seating area featuring decorative trunks. A pool table is vibrant with colorful balls, while a nearby hot tub is inviting with bubbles gently rising.

Home in Pocono Summit

4.9 out of 5 average rating, 277 reviews

Enchanted Castle - Unique & Charming Getaway

Recently renovated unique Harry Potter inspired 4BR/2BA 1600sq ft castle themed home near Kalahari, Mt Airy Casino & Camelback! Enjoy a private fenced yard with Hot Tub, Sauna, Fire Pit, Mini Golf, Swing Set, Patio & BBQ Grill. Inside: Pool Table, Ping-Pong, Chess, Scavenger hunt, Smart TVs, WiFi, Netflix & Family Games. Perfect Poconos getaway with comfort & fun for all ages—very close to top attractions, skiing, waterparks & dining. Great for families, couples & group retreats.

Guest favorite

A spacious living area is highlighted by a flat-screen TV mounted on the wall. Natural light filters through large windows, illuminating the wooden floors and soft furnishings. A coffee table holds a decorative bowl, surrounded by vibrant yellow flowers that add a welcoming touch.

Chalet in East Stroudsburg

4.92 out of 5 average rating, 436 reviews

Cozy House - Lovely Fairytale TreeHouse - Hot Tub

Experience a nature lover's paradise in this stunning house with serene surroundings for play and relaxation. Perfect for families, it sleeps up to 6 adults and features a spacious living room, entertainment loft, and a 7-person hot tub for post-exploration relaxation. With its prime location, you're close to major Pocono Mountains attractions like Camelback Water Parks, Crossing Outlets, Delaware Water Gap, and more—the ultimate destination to explore this scenic region.

Superhost

A cozy sleeping area features a spacious bed dressed in a bear-themed comforter. Two bedside tables with lamps are positioned on either side, and a nature-themed artwork adorns the wall, contributing to a calming atmosphere in the room.

Home in Lake Harmony

4.92 out of 5 average rating, 106 reviews

Black Bear Cozy Cabin, Lake View Dr. Dog friendly.

This property is Dog friendly on Lakeview Drive, with 2 bedrooms that sleeps 6 in Lake Harmony. You must be age 30 to rent. No parties allowed. It’s a 5 min walk to the lake to fish, swim or kayak & 0.3 mile to restaurants/bars on Lake Harmony. We are located close to Split Rock Resort for family fun games, mini golf and water park. Wine & Cigar Fest. Back yard gas grill & fire pit & indoor wood burning fireplace. We are close to Pocono raceway and Skiing at JFBB.

Guest favorite

A cabin is shown nestled among trees, with a wooden deck overlooking a gently flowing stream. Vibrant autumn leaves contrast against the dark exterior of the cabin, enhancing the natural setting. The scene captures the peacefulness of the surrounding landscape, inviting relaxation.

Cabin in Accord

4.94 out of 5 average rating, 112 reviews

Peaceful Cabins by the river, excellent wifi!

Just figured out availability for our cabins this summer! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” and super chic Inness.

Guest favorite

A scenic view from a wooden deck showcases rolling green hills and tall trees. A tranquil pathway winds through the landscape, leading to nearby homes. Gentle sunlight filters through the foliage, enhancing the natural beauty of the surrounding area.

Home in Palenville

4.96 out of 5 average rating, 166 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

Top guest favorite

A charming country house is set against a backdrop of rolling hills, featuring a welcoming porch and large windows. Lush green grass surrounds the property, with a few trees adding to the natural scenery. Outdoor seating is visible in the foreground.

Cottage in Livingston Manor

4.99 out of 5 average rating, 155 reviews

Nicks Place

Open space kitchen, dining, and living room All in a cozy country setting . Two bedrooms with queen beds and two single beds in spacious loft. Bright and sunny. Outdoor grille, firepit, and sun porch. Close to hiking trails, one mile from state gamelands. Minutes from Beaverkill and Willowemoc rivers. Close to three local breweries and distillery. Within an hour of ski resorts. Super quiet location, off the beaten path.