Family-friendly holiday rentals in Monticello

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Monticello

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

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Guest favourite

Chalet in Tafton

4.85 out of 5 average rating, 131 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

Superhost

Cabin in Albrightsville

4.91 out of 5 average rating, 340 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.

Guest favourite

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 apartment. See Guidebook for Seasonal Fun! Escape Pocono traffic & enjoy the countryside. *Close to 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 coming soon.*3-day all Holidays. 1 dog<40pd.

Top guest favourite

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 favourite

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 favourite

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 favourite

Home in Kerhonkson

4.95 out of 5 average rating, 355 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Guest favourite

Chalet in East Stroudsburg

4.92 out of 5 average rating, 435 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

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 favourite

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 favourite

Home in Palenville

4.96 out of 5 average rating, 164 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 favourite

Cottage in Livingston Manor

4.99 out of 5 average rating, 153 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.