Holiday rentals in Monticello

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

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!

Charming Catskills Lakefront Home—2 hrs 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.

Barton bungalow cozy relaxation on 7private acres

Stay at the Barton Bungalow! This cozy, beautifully renovated bungalow sits on 7 private acres. It has a rustic feel with all the modern amenities. We have high speed WiFi so you can work from home. Enjoy some R&R in the hammock, relax by the fire pit or bbq . We are 2 miles from Walnut Mountain Park and less than 10 miles away from Bethel Woods. Try your luck at Resorts World Catskills or go for a splash at Kartrite indoor water park. The trendy Livingston Manor is less than 20 minutes away

Canoe•Fireplace+Pit•Renovated & Chic•Fall Foliage

Escape to The Original Bungalow, part of the @boutiquerentals_ collection—a newly renovated Scandi-chic retreat just 2 hours from NYC. Paddle the canoe or SUPs on the lake, take in the vibrant fall foliage as you stroll to the local waterfall or forest trails, or visit Bethel Woods Center for the Arts, Woodstock site, apple orchards, breweries, art galleries & charming towns like Callicoon & Livingston Manor. By night, gather at the fire pit or cozy up by the fireplace with a book or movie.

Romantic Agrihood Getaway Bungalow-Fireplace/WiFi

Spend some time in a classic Catskill Bungalow! Beautifully renovated and nestled in the quiet yet all-inclusive Hamlet of Hurleyville; this clean space offers a great place to rest your head and bones. In the cooler months enjoy a beverage by the fireplace or in the warmer months have one on the porch and look out at all the green there is around. Walk to town for dinner, shopping, or a movie at the PAC (VisitHurleyville.org). Please see below for more information on our pet policy.

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.

Lakefront Catskills Fall Foliage Dream

Serene getaway to a lakefront luxury MidCentury house 90 mins from NYC/3 hours from Philadelphia. Equipped with dock, firepit, outdoor deck and patio, guitar, instruments for family music making, games, books, and lake toys galore. 3-beds, 2-baths, fully equipped kitchen, large dining & living areas. Minutes to Callicoon, Livingston Manor, Narrowsburg, Bethel Woods, spas, Catskills Casino, Monticello Racetrack, Kartrite Waterpark, Holiday Mountain.

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.