Pet-friendly vacation rentals in Monticello

Element House - Off Grid Hideout

Unwind and reconnect with nature in this rustic and comfortable retreat nestled at the edge of a blueberry field. Surrounded by serene Catskills countryside, you’ll feel a world away, yet still be just minutes from outdoor activities, a thriving food scene, and Bethel Woods just 35 min away. Inside, you’ll stay cool with AC, a cozy queen bed, kitchenette, dining table, reliable wifi, and full bath. Outside, relax by the fire pit or cook on the charcoal grill. We are an LGBTQ+ inclusive space.

Pedal Boat+SUPs•Hot Tub•Treehouse Views•Renovated

Escape to The Treehouse Bungalow – part of the @boutiquerentals_ collection. This 1930s Arts & Crafts cabin combines Scandi-chic style with modern comfort, offering treehouse views, a hot tub, fire pit, BBQ & work-from-home den. Guests can paddle White Lake with our pedal boat or explore nearby lakes with the SUPs. Enjoy fall foliage hikes & drives, Bethel Woods Center for the Arts, the Woodstock site, apple orchards, breweries, art galleries & charming towns like Callicoon & Livingston Manor.

Cozy A-Frame | Hot Tub, Fire Pit & Pet-Friendly

Escape to the Cedar Haven A-Frame in Damascus, PA – the perfect romantic hideaway just a short drive from NYC. Nestled in peaceful woods, this cozy 400-square-foot retreat offers all you need for a relaxing escape. Soak in the private hot tub, roast marshmallows by the fire pit, or unwind to music as you watch the forest through wide windows. Whether celebrating a special occasion or just needing time away, the tiny cabin invites you to unplug, reconnect, and make memories in nature’s embrace.

Chic Cabin on Callicoon Creek

***FEATURED IN ARCHITECTURAL DIGEST, TRAVEL & LEISURE, APARTMENT THERAPY, AND FODORS TRAVEL*** Set back on a small private road, this cabin dating back to the 1800s is perched above the Callicoon Creek, popular with fly fishermen casting for rainbow trout. Head up the wooded driveway and find yourself in a serene, green clearing all your own. The cabin and studio make for a peaceful getaway, shielded from the surroundings, but incredibly convenient for reaching nearby towns and activities.

Canoe•SUPs•Fireplace+Pit•BBQ•Scandi-Chic•Renovated

Escape to The Original Bungalow, part of the @boutiquerentals_ collection—a newly renovated Scandi-chic retreat just 2 hours from NYC. Take in the vibrant fall foliage as you stroll to the local waterfall or forest trails, paddle the canoe or SUPs on the lake, 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.

Dreamy Catskills mountain getaway w/ yoga studio

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

Lakefront Catskills Kayak/Swim Luxury Mid-Century

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.

Dutchhillcottage, gem in the southern Catskills.

The Dutch Hill Cottage is a renovated, rustic chic design 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 Cattskils, perched on a peak at the forests edge with expansive views all the way down to the Never Sink river with amazing suntset views from our huge deck. Plenty of ameneties and we welcome your petdog!