Family-friendly vacation 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 favorite

Cabin in Livingston Manor

4.97 out of 5 average rating, 280 reviews

Experience The Zen House

Enjoy your own private indoor HD movie theater with 5.1 Bose Surround Sound and leather recliner seats, a spa with a cold plunge pool and sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Here are some of the key amenities: -Hot Tub (2021) -Sauna & Cold Plunge Pool -Private 12 Person Movie Theater (you can plug in your device) -Table Tennis/Ping Pong and much more! Check us out on ig: @zenhouseny

Guest favorite

Cabin in Smallwood

4.85 out of 5 average rating, 223 reviews

Comfortable Catskill Cabin minutes to Bethel Woods

Comfortable, private home very close to Bethel Woods on a quiet dead-end street in a desirable mountain lake community. Two bedrooms & a loft, WiFi, heat/AC, deck with BBQ grill, picnic table & fire pit. In the heart of the Sullivan County Catskills centrally located to the many attractions this vacation recreation area has to offer: site seeing, concerts, hiking, camping, skiing, breweries/wineries, boating, parks, antiquing, casinos, wedding venues, museums, Delaware River, hunting/fishing etc

Guest favorite

Home in Bloomingburg

4.8 out of 5 average rating, 513 reviews

Δ Scenic Hiking Paradise with Deck and Fire Pit!

Relax at this peaceful place atop the Shawangunk Mountain Ridge. You'll enjoy plenty of room at this wooded oasis! • On 2 wooded acres • Beautiful area • Deck off kitchen w nice grill • Lawn fire pit w seating & string lights • Adjacent to 1600 acres of State Forest with official hiking trails & Amazing Views right near house • EXTRA Professional Covid Cleaning • Home gym & treadmill • 3 bedrooms • Large living room with 2 sleeper sofas • Near great outdoor and indoor attractions

Superhost

Cabin in Maplecrest

4.95 out of 5 average rating, 200 reviews

The Cabin - Ski House near Windham

The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Guest favorite

Cabin in Smallwood

4.97 out of 5 average rating, 230 reviews

Beautiful & Secluded Streamside Catskills Cabin

Private & secluded Smallwood cabin sleeps 6. See & Hear the stream flowing when you pull up. Large great room with fireplace & windows overlooking backyard stream. 1 master bedroom, 1 separate guest room, 1 open sleep loft (2 twin beds). Enjoy evenings on the deck, or by the outdoor fire pit listening to the stream that leads to a small waterfall. Enjoy the swim pit right in your backyard! Outdoor Shower! Close to Bethel Woods, hiking & White Lake dining. Minutes to Toronto Reservoir.

Guest favorite

Home in Cochecton

4.9 out of 5 average rating, 546 reviews

Woodsy Retreat, Sunny Home with Paths and Stream

This lovely hand-made home in the woods, lined with windows, flooded with light, has 2 bedrooms and 2 full baths, and a large wraparound deck facing a feisty stream. It has 10 hilly acres of woods with its own paths to wander. Work, relax and play in its inspiring kitchen and lofty spaces stocked with albums, movies, books, art supplies, and instruments. Enveloped in nature, yet only a 10 minute drive to local hot spots including Narrowsburg, Callicoon, Skinners' Falls and Bethel Woods.

Guest favorite

Tiny home in New Paltz

4.99 out of 5 average rating, 788 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

Guest favorite

Guesthouse in Mongaup Valley

4.99 out of 5 average rating, 388 reviews

Good Vibes Studio in the Woods

Hi! We're Jen, Jacob, and Jude. Welcome to our peaceful studio apartment with good vibes. One memory foam queen bed and one futon. Whether you want to just get away and enjoy the woods or need a place to crash that is super close to Bethel Woods, Resorts World Casino, Kartrite Waterpark and all of the delicious White Lake restaurants, our studio is the place for you! And we are right next door if you need anything at all. Come experience Mother Nature with us!

Guest favorite

Farm stay in Callicoon

4.96 out of 5 average rating, 201 reviews

Country road please take me home!!

Are you looking for rest & relaxation or fun in the Catskills. Come enjoy our warm, cozy home away from home. Our guest mobile home is located on a quiet country back road, but yet close to dining and outdoor activities that the Catskills has to offer, rafting down the Delaware & enjoying concerts at Bethelwoods. The possibilities are endless. We now have Spectrum internet. Please note that we do reside on an active farm. This could be a wonderful experience!

Guest favorite

Cottage in Phoenicia

4.89 out of 5 average rating, 850 reviews

Romantic hot tub cottage. Breweries/skiing nearby

Your perfect romantic country cottage with private courtyard, steamy outdoor hot tub and fire pit offering the feeling of complete seclusion yet only a couple of minutes walk from fabulous Main Street speciality stores and restaurants. 2 minutes to Woodstock Brewing and the famous Phoenicia Diner . Bike the rails with Rail Explorers just around the corner or hike the beautiful Ashokan Rail Trail from Boiceville ( 8 minutes )

Guest favorite

Home in New Paltz

4.97 out of 5 average rating, 728 reviews

Victorian Haven

Victorian Haven is located near the Shawangunk Mountains that extends for over 20 miles and reaches 2,200 feet in height at Sam's point, the highest elevation on the ridge. In addition, the Wallkill River provides unspoiled and picturesque spots for hiking, fishing and/or picnics. Gardiner has a beautiful rail trail that follows the path of the 1860's railroad and provides a great opportunity to hike, bike or ski.

Superhost

Cabin in Huguenot

4.94 out of 5 average rating, 264 reviews

Tranquil Lakefront Cabin!

This Warm LAKEFRONT Home Grabs Your Soul and Forces you to Decompress Instantly. Enjoy the Large Well Appointed Screened Porch with Glass of Wine/Cup of Coffee as you Gaze over the Rustic Lake thru Stately Oak Trees and Cranberry Bogs. Boats Included!!! $50 Per Pet Per Stay After Host Approval.. Firewood Stored In The Rear Of The Tool Shed..