Family-friendly vacation rentals in Monticello

Lake Access—Canoe—SUPs—Innertubes—FirePit—BBQ—Chic

Only 2 hours from NYC, stay at @boutiquerentals_' Scandi-inspired 'The Original Bungalow' in the Catskills featuring lake access, canoe, paddle boards+ inner tubes. Come for the ample swimming opportunities, pretty strolls along the lake, forest hikes, Bethel Woods Center for the Arts, original Woodstock site, proximity to the Delaware River, craft beverage trail & charming river towns with great dining+shopping. At night, grill up some delights on the BBQ & relax on the deck or by the fire pit.

Cozy Catskills Chalet • Fire Pit • Covered Deck

Stylish, newly renovated Catskills chalet near Bethel Woods Center for the Arts. Walk to White/Kauneonga Lake, lakefront dining, and a boat launch. Unwind by the fire pit, grill on the covered deck, or enjoy the spacious backyard with a playground, sports gear, and apple trees. Inside, relax with vinyl records, board games, puzzles, and a fully stocked kitchen. Close to hiking trails, ski resorts, the Delaware River, and charming nearby towns. Perfect for families, couples, and concert weekends.

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

Blue House | Cedar tub•BBQ•fire pit•stargazing

Nestled in the Catskills Mountain region, between the Delaware and Hudson Rivers in the community of Monticello. Insta @bluehouseofcatskills offers a year-round retreat away from the hustle and bustle of the city. Spectacular stary nights, wildlife in the backyard, hiking trails, swimming and skiing all a short drive away. The Blue House is a wonderful getaway for all to enjoy. Modern and contemporary design the Blue House offers comfortable king and queen bedrooms and a spacious living area.

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.

Catskills Lakefront Haven w/ Hot Tub & Game Room

Indulge in the serenity of our lakefront haven, situated along 100ft of Sackett Lake's private shoreline. Here, year-round enjoyment is a promise - be it summer swimming, kayaking, or winter ice fishing and snowmobiling. Mere minutes away from Holiday Mountain, Casino, Waterpark, breweries, and Bethel Woods, our modern home boasts a vast deck and an 8-person hot tub. This is more than just a getaway; it's a sanctuary for creating unforgettable memories. Don't miss the chance to experience it!

Lakefront Home in the Catskills

Quiet & Comfortable house on Sackett Lake w/dock. 3 Kayaks and canoe On our adjacent property for use Located near everything. Large deck w/BBQ. Fire pit area by lake & patio area in front Close to Kartrite water park, Resorts World, Bethel Woods , Breweries & wineries. So much to do right near by, or do nothing at all but relax & listen to the sounds of the country. Plenty of Outdoor furniture. Large front lawn & ample parking. Property not suitable for children under the age of 7.

Lakefront • Hot tub • Kayaks • Fire Pit • Fishing

A romantic lakefront escape ideal for one or two couples, or close friends seeking beauty, comfort, and connection. Wake to sparkling water, unwind in the hot tub beneath starlit skies, and share long evenings by the crackling firepit with firewood provided. Enjoy open-concept living, a fully equipped kitchen, outdoor dining on the spacious deck, peaceful lake views and private kayaks ready for sunrise paddles. Close to Bethel Woods, scenic trails, charming towns, and great local dining.

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.

Dutchhillcottage, gem in the southern Catskills.

Just 85 miles from NYC! Rustic chic design cottage waiting for you and your friends or family to enjoy. Private, comfy & cozy country getaway with amazing views situated on 10 acres of rolling hills in the southern Catskills, perched on a peak at the forests edge with expansive views all the way down to the Never Sink river with beautiful suntset views from our huge deck. Plenty of ameneties. Petdog friendly. Just 2 miles down the road from newly updated Holiday Mountain Ski Resort!

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

Recently 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.