
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.

Cozy Catskill Getaway Upstate NY - 5 min to casino
Kick back and relax in this cozy styled cottage! Centrally located near shopping plazas including Shoprite, Walmart and Marshalls. Also close to eateries, fast food restaurants, and Resorts World Casino. Explore the Catskills and come back to stay in a warm cottage. Although it is centrally located, it's pushed back enough that you still get the country living feeling. Located on 2 acres of land, you're sure to hear the birds chirping! There is a pull out couch available for an additional guest.

Hot Tub, Playground, 3 Acres, and Much More!
Relax with the whole family at this peaceful cottage in the trees 5 minutes from Bethel Woods - check out their upcoming events! Recently renovated cottage with hot tub, an electric fireplace, washer and dryer, dishwasher, and smart TVs. Family-friendly features include a baby gate, potty training seat, high chair, toddler-safe bunk beds, and toys Outdoor features include 2 fire pits, trampoline, jungle gym, basketball hoop, walking path, stream w/ waterfall, and 3 acres of woods to explore

Fireplace—Renovated—Near Skiing & Tubing—Chic+Cozy
Escape to The Original Bungalow, part of the @boutiquerentals_ collection—a newly renovated Scandi-chic retreat with a cozy fireplace & fire pit in a woodland backyard. Located just 2 hours from NYC in the Catskills (one of Travel+Leisure’s 50 Best Places), Smallwood is a destination in itself: walk along the lake, waterfall or hike the forest trails. Nearby are Holiday Mountain (skiing+tubing), Kartrite Waterpark, Bethel Woods + dining & shopping in Callicoon, Livingston Manor & Narrowsburg.

Catskill mountain getaway
Fits 4 adults and 2 children.Entrance to lake 100 feet away with boat for you to use. Fish , swim , boat , picnic table , dock in middle of lake ,nearby hiking. Back patio has swing chair and picnic table , hammock for a nice quiet relaxing time .enjoy wildlife birds, deer, etc. always on standby to answer question. our local handyman is ready to address any issues you may have. Full kitchen with all your cooking needs. This is a perfect vacation spot to have fun and make beautiful memories.

Cozy Catskills Cabin
Give yourself time away from the city and closer to nature. Go for a hike, a dip in the lake, or simply relax, take your shoes off and put a good record on. Casa Smallwood got its name from the hamlet of Smallwood, a quaint community of cabins from the 30's and 40's, nestled less than 2 hours from NYC. We're only 7 minutes away from BethelWoods Arts Center, the original site of the 1969 Woodstock Festival. Come stay with us and surround yourself with beautiful trees, lakes, love and peace.

Cozy Barn Cabin near Ski Mountain & Bethel Woods
1200 sq. ft Post & Beam 2 story Barn Cabin set on 18+ acres of property w/1250 ft. of rd frontage leading to this gem. Amish wood furniture and a wood burning stove. Open loft concept on 2nd floor offers 1 king bed, a trundle bed with 2 twins (sleeps 4), 1/2 bath & closet space. Downstairs offers kitchen, dining room, living room and full bath. Private park on property w/hammock, volleyball & basketball court, swing set, slide & playhouse, yard games (in house & shed) barbecue & firepit.

Riverfront Ski Chalet
Escape to the country air at Sean & Brad's riverfront chalet on the Neversink River. Formerly a popular ski shop and yoga studio, this fully renovated property offers you every possible amenity. Walk across the street to launch your kayak or toss a line into some of the best trout fishing around, roast s'mores around the fire or visit the Resorts World Casino, just 5 minutes away. Golf, hiking, mountain biking, local breweries and distilleries...all just a short distance as well.

Hot Tub, Fire Pit/Place, Snow Tubing/Ski Mountain
Coined the "Eikonic Box" for its iconic look- you'll be amazed by the flying boxes with unique views of the gorgeous forest views. Escape the ordinary and immerse yourself in the modern comfort of this stylish 3-BR retreat. Designed with sustainability and creativity in mind, our container home offers a one-of-a-kind lodging experience for those seeking a blend of innovation & relaxation. Book your stay today and experience the charm of container living! Message me for Q's!

Modern Upstate Escape with Outdoor Sauna
Newly renovated two bedroom, two bath cottage with four person barrel sauna at Swinging Bridge Reservoir, Sullivan County's largest motorboat lake. Updated amenities and mid-century and modern furniture provide a welcome respite from the city just 90 miles away. Take in the local scenery, catch a show at the Forestburgh Playhouse or stop into some of the local vineyards and restaurants. For a low key weekend, hang out by the fireplace playing some records and cooking a meal.

Private lake cabin w/hot tub, views and fruit
Catchers Pond is perched atop a hill with views overlooking a private pond featuring a swim platform, dock, Jacuzzi, outdoor shower, fire pit and a fruit orchard of peach, pear and apple. It is perfectly secluded and close to everything you might need for your stay being just 5 minutes outside Mountaindale. Its rustic, charming and wild. A great place to slow down, reconnect and watch seasons change. The cabin sits on 55 quiet acres with no other houses in sight.

Lovely Cottage w/ Jacuzzi+Woodstove!
Nestled in the hamlet of Smallwood, only 2 hours from NYC, this newly renovated cottage is the perfect getaway from the city and an oasis surrounded by nature. This cottage is perfectly located for access to surrounding lakes and seasonal beaches, hiking trails as well as exploring and discovering the lovely Catskills region. The cottage features a wood stove, spacious deck, a fire pit as well as an all-season jacuzzi to enjoy day or night.

Trails Head Tiny House
Private and off-grid tiny home near the Neversink Unique Area hiking trails. This tiny house is approximately a tenth of a mile from guest parking. A marked trail to the site with trail markers for easy direction. This tiny house has solar powered WIFI and lights. This is not an insulated structure and during the winter months there is no running water. The outhouse is located about 50 feet from the tiny house.
Popular amenities for Monticello family-friendly rentals
Family-friendly home rentals with a hot tub

The Water House - Winter Spa on a Cascading Brook

Lakefront • Hot tub • Kayaks • Fire Pit • Fishing

the tree house, by camp caitlin

Magical Lake House-Hot Tub-Deck-Outdoor Kitchen

Ye Little Wood | Cozy Forest Cottage with Hot Tub

Chic Cabin on Callicoon Creek

Catskills Cabin, Hot Tub, Wood Stove, King Bed

Map Maker's Cabin
Family- and pet-friendly home rentals

Remote Waterfall Cabin at Swiftwater Acres

The Waterfall Casita: A-frame with 30ft Waterfall

Private Riverfront, Magestic View, Wildlife, Sauna

R & R On The Knoll

bungalow summer cottages on the lake Catskills

Lidar West

Lakeside Studio on White Lake

Cozy Cottage in Popular Narrowsburg
Family-friendly home rentals with a pool

Stunning Mountain Cabin w/ Pool & Hot Tub

Appalachian Lodge Top Floor w/views

Airy & Private Escape on Mountain Rest Road *Pool*

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

Bella Cottage w/Cozy Fireplace & BBQ, Fall Getaway

Secret Getaway Nestled in a Woodland Setting

Family Fun w Hot tub/Pool/Sauna near Ski Holidaymt

Woodland Hideaway: Sauna, Tennis Court & 15 Acres
Quick stats about holiday rentals that are family-friendly in Monticello

Total holiday rentals
Explore 30 holiday rentals in Monticello

Nightly prices starting at
Monticello holiday rentals start at $139 NZD per night before taxes and fees

Verified guest reviews
Over 420 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
30 of Monticello holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Monticello rentals

4.8 Average rating
Monticello stays are highly rated by guests—averaging 4.8 out of 5!
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- Hunter Mountain
- Upper Delaware Scenic and Recreational River
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Elk Mountain Ski Resort
- Bethel Woods Center for the Arts
- Bushkill Falls
- Minnewaska State Park Preserve
- Windham Mountain
- Delaware Water Gap National Recreation Area
- Resorts World Catskills
- Sunset Hill Shooting Range
- Brotherhood, America's Oldest Winery
- Promised Land State Park
- Mount Peter Ski Area
- Shawnee Mountain Ski Area
- Hunter Mountain Resort
- Plattekill Mountain
- Pocono Mountains
- Bear Mountain State Park
- Wawayanda State Park
- Opus 40
- Claws 'N' Paws
- Tobyhanna State Park




