Family-friendly holiday rentals in Monticello

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.

renovated–hot tub–near skiing+tubing–cozy & chic

Escape to @boutiquerentals_' The Treehouse Bungalow–a renovated yet cozy 1930s Arts & Crafts cabin with hot tub, mountain views, fire pit & electric fireplace. Located 2 hrs 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 is dining & shopping in Livingston Manor, Callicoon & Narrowsburg, skiing/tubing at Holiday Mountain, Bethel Woods Center for the Arts & Kartrite Waterpark

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.

BirchRidge A-Frame: Sauna/Firepit/King Bed/7 Acres

Nestled in the Catskills Forest, less than 2 hrs from NYC, you'll find Birch Ridge A-frame! This gorgeous 2-bedroom cabin is set on 7 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that creates a magical stay with breathtaking views. This is the perfect place to relax, sit in the barrel sauna, hike through the private forest, roast marshmallows over the fire, and soak up the sounds of nature. A space that’s made for creating memories that will last a lifetime!

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.

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.

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.