Holiday rentals in Monticello

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.

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.

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.

Remote Waterfall Cabin at Swiftwater Acres

Deep in a lush oak forest, on the bank of Bushkill Creek sits this hidden oasis. This is simply THEE most private abode in the entire area. Situated just feet from the water, the falls can be seen and heard from every room within the cabin’s charming, rustic interior. This spectacular 45 acre parcel is set within a vast reserve of state land: an oasis within an oasis. Just 90 minutes from NYC, this is a truly sublime atmosphere, perfect for those seeking a rejuvenating and inspiring getaway.

Modern Catskills Retreat•10 Acres•Hot Tub•Firepit

Welcome to a dream escape, tranquil 3-bedroom modern home that's less than 1-mile off the Delaware River! Built in 2023 and nestled on 10+ acres of pristine countryside delivering peace, quiet and privacy. This exceptional retreat seamlessly combines rustic charm with contemporary luxury, guaranteeing an unforgettable stay. The home features 3 furnished bedrooms sleep up to 7 (3 queen beds, 1 w/ trundle) + a spacious entertainment room flowing directly from the kitchen ideal for hosting.

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.

Dreamy Catskills mountain getaway w/ yoga studio

This stunning house has been renovated and offers total privacy and serenity - sitting on 5 acres at the end of a quiet road. The Mountain Terrace has an indoor wood stove, a deck with a beautiful view, a fire-pit, 3 bedrooms and 2 bathrooms and a double high ceiling in the main living space. There is a washer/dryer, a dishwasher an artist cabin and a private yoga studio. An easy 15 min drive to Livingston Manor for great restaurants, shopping and activities. Pet friendly.

Unique Container Home w/ Hot Tub, Fire Pit & More!

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 today and experience the charm of container living! Message me for Q's

Forest Spa Retreat on Cascading Brook • 90 Min NYC

Tucked into an evergreen forest, The Water House is a private spa retreat set above a cascading brook—where flowing water shapes your stay. Spend slow mornings on the deck, unwind in the hot tub, and gather by the fire pit under the stars. Find a quiet moment beside the Japanese-inspired pond. Inside, soft textures and vintage style create a warm, calming atmosphere designed to reconnect you with nature while offering the restful comfort of a boutique retreat.

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!