Family-friendly holiday rentals in Monticello

Canoe—SUPs—Innertubes—Chic—Renovated—Fire Pit—BBQ

'The Original Bungalow,' part of the @boutiquerentals_' collection, is a Scandi-chic renovated bungalow surrounded by stunning trees. Located only 2 hours from NYC, Smallwood is a destination in itself: walk along the lake or waterfall, or take the canoe or SUPs for a paddle (seasonal). Nearby are Bethel Woods Center for the Arts, breweries, Livingston Manor & cute Delaware River towns with dining+shopping. In the evening, unwind by the fire pit or curl up by the fireplace with a book or movie.

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

Cozy Lakefront Catskills Cabin—2hrs from NYC!

This beautiful lakefront cabin is located at the end of a peaceful road adorned with tire swings and wildflowers. It is situated in a private community on a SMALL 3 acre lake, offering the perfect setting to enjoy morning coffee on the dock, taking refreshing afternoon swims in the lake, going for evening kayaking rides, and stargazing. You can unwind in our hammock nestled amidst the ferns next to a tranquil stream. We offer 2 kayaks and 1 SUP for your enjoyment. Best of all, 2 hrs from NYC.

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!

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

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.

Secluded lakefront home With an EV charger

Welcome to your oasis on the Swiniging Bridge Reservoir! Only 90 minutes from NYC, but a world away. A complete glass wall facing the water allows guests to take in the views and sounds of a babbling brook that feeds into a motorboat lake. This brand new house sleeps 6 adults (or 4 adults and 3 children) and features a full kitchen, free WiFi, bedding, linens, and toiletries. A canoe and paddleboat are also available for your use!

Luxury Lakefront Estate | Private Beach & Spa

✓ Lakefront home w/ sandy beach ✓ Covered hot tub ✓ Massive deck w/ outdoor kitchen + BBQ ✓ Private dock ✓ HDTV 55” w/ Netflix, Hulu, Prime ✓ 336 Mbps wifi ✓ Driveway for 6 cars + land across the street for 6 more ★”The view and the lake access was just what we wanted” 3 min→ Swinging bridge marina 20 min→ Resort Worlds Casino @thestarlightny