Vacation rentals in Woodbourne

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Top-rated vacation rentals in Woodbourne

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A wooden deck extends from the chalet, offering a view of lush greenery and rolling hills under a clear blue sky. Sunlight filters through the trees, creating dappled light on the ground. The vibrant colors of autumn foliage can be seen in the landscape.

Chalet in Grahamsville

4.95 out of 5 average rating, 174 reviews

Catskills mountain view chalet

Come and enjoy our Catskills mountain view chalet. Escape the chaos of the city for peace and serenity. In our home you'll find an open concept kitchen/dining and living room space, a huge deck, 2 bedrooms, a newly renovated bathroom and a loft work space. Take in the country skyline view with a glass of wine on the deck while listening to meditative sounds of the babbling brook. Don't forget to bring groceries as the best way to enjoy the chalet is with a home cooked meal with those you love

Top guest favorite

The A-frame cabin is surrounded by vibrant autumn foliage, showcasing hues of gold and orange. A welcoming red door stands out against the green exterior. A wooden deck extends from the cabin, providing an inviting entry point amidst the natural landscape.

Cabin in Margaretville

4.99 out of 5 average rating, 178 reviews

The Waterfall Casita: A-frame with 30ft Waterfall

Nestled among Hemlock trees & steps from a 30 ft waterfall is our cozy A-frame cabin. Sitting on 33 private acres connected to state land, enjoy waterfall views while sipping coffee in front of the fireplace. The casita was intentionally designed to feel like a home away from home. In summer, cool off in the waterfalls & private streams, in autumn take in the stunning foliage & in winter ski/snowboard at Belleayre (25 mins away). Alder Lake & the Pepacton Reservoir fishing are a 10 min drive.

Guest favorite

A hot tub sits on a wooden deck surrounded by autumn foliage, illuminated by warm string lights. Nearby, a gently flowing brook is visible, reflecting the soft glow from flickering candles arranged on the deck. The serene setting offers a peaceful atmosphere for relaxation.

Cabin in Wurtsboro

4.96 out of 5 average rating, 337 reviews

Spring Spa on a Cascading Brook - The Water House

The brook flows through an evergreen forest creating a nourishing environment and the perfect setting for a relaxing and rejuvenating spa retreat. The living/dining room, hot tub/deck, and gas fire pit are set overlooking the cascading brook, ideal for entertaining, meditating or simply as an enjoyable natural muse. The soft, cozy and elegantly vintage styled interior is illuminated and warmed with central heating, ambient lighting and a home surround sound entertainment system with karaoke.

Guest favorite

A private deck area features a wooden chair beside a neatly stacked pile of firewood. The entrance displays a large sliding glass door, illuminated from within, revealing a warm interior. Soft outdoor lighting complements the natural surroundings of greenery.

Tiny home in Livingston Manor

4.97 out of 5 average rating, 130 reviews

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.

Top guest favorite

An open-plan living area showcases large windows that provide natural light and serene views of outdoor greenery. A spacious seating arrangement includes a sofa and armchairs, complemented by a dining table for six. Decorative elements and modern amenities are present throughout.

Cabin in Woodbourne

5 out of 5 average rating, 200 reviews

Catskills Overlook Mountain Sanctuary

Our cabin is located in the stunning Catskills area of Neversink, NY. A perfect hideaway to embrace a mountain visit, with modern conveniences. 2 acres of private, park-like land, that’s incredibly zen and encourages wandering. Sit near our koi pond, or relax on our decks–each with a view of Lake Paradise. A peaceful sanctuary, our 2 Bedroom cabin is complete with a seasonal (Oct-Apr) wood-burning fireplace, views of nature, and modern amenities for those who don't want to fully unplug.

Guest favorite

A cozy living area features a plush green sofa and a round wooden coffee table. A bright yellow chair adds a pop of color. Natural light fills the space through large windows, highlighting the wooden paneling and a wood stove in the corner.

Home in Woodbourne

4.94 out of 5 average rating, 147 reviews

Cozy Catskills Cabin with Grill & Fire Pit

My cabin in rural, woodsy Catskills is perfect for a relaxing getaway/escape from the city. Read a book or binge a show in the cozy living room, cook an elaborate (or simple) meal in the big, recently renovated kitchen, grill and/or enjoy the fire pit on the patio, & get out in nature with hikes, a lake, & slopes nearby! 25 minutes to all the cute Catskills towns like Livingston Manor, Mountain Dale, & Ellenville with great restaurants, bars, and shops! Also, only 5 minutes from Hemlock spa!

Guest favorite

Two wooden Adirondack chairs are positioned on a dock overlooking a calm lake at sunset. A kayak with an oar rests nearby, and the water reflects vibrant hues of orange and pink, bordered by trees in the background.

Cabin in Ferndale

4.92 out of 5 average rating, 224 reviews

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.

Top guest favorite

The A-frame cabin is surrounded by trees and set on a grassy area. A fire pit with seating is situated in front, with smoke rising gently in the evening light. The cabin's large windows reveal a welcoming interior, illuminated by natural light.

Home in Jeffersonville

4.99 out of 5 average rating, 191 reviews

BirchRidge A-Frame: Sauna/Firepit/Hiking/King Bed

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 6 private acres with hiking areas and a seasonal stream. Enjoy the wall of windows that create 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!

Top guest favorite

A cozy living area is highlighted by a corner fireplace and a flat-screen television. A sectional sofa with cushions and an armchair create a comfortable seating arrangement. A decorative shelving unit displays greenery and decorative items, while warm lighting adds a welcoming touch.

Bungalow in Hurleyville

5 out of 5 average rating, 145 reviews

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.

Top guest favorite

A treehouse structure is observed elevated among lush greenery, supported by a prominent tree. The exterior features dark siding, a distinct gable roof, and vibrant orange doors. A spiral staircase leads to the entrance, while a natural clearing surrounds the base.

Treehouse in Wallkill

4.99 out of 5 average rating, 325 reviews

The Treecastle at the Roundhouse Homestead

The Treecastle started as a vision when I was a child, but came to life during the quarantine of 2020. Escaping into the woods and surrounded by nature, the treecastle is supported on one end completely by a mature pin oak with hardware from Treehouse Masters TV show. Attention to detail shows in this romantic stay that will surely be a memory to last a lifetime. For more photos and videos check out our social media pages : treehouseandchill

Guest favorite

A cabin sits amidst tall trees beside a gently flowing creek. The red roof contrasts with the surrounding greenery, while natural light filters through the foliage. The tranquil water reflects the tree canopy, creating a serene woodland atmosphere.

Cabin in Livingston Manor

4.95 out of 5 average rating, 353 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek, gaze out XL windows, or cozy up by the fire—every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor—a quintessential Catskills town—and less than 2 hours from NYC.

Guest favorite

A welcoming living area features wooden walls and vaulted ceilings with exposed beams. A plush blue sofa and grey armchairs surround a glass coffee table. Sunlight filters through multiple windows, enhancing the warmth of the space. A dining table is positioned near the windows.

Home in Woodbourne

4.83 out of 5 average rating, 234 reviews

Escape 2 The Catskills

Explore all The Catskills has to offer in our newly renovated home that is like no other!! Our home is a glamorous blend of rustic and industrial styles. A beautifully decorated spacious 3 bedroom with a huge entertainment/family room on the lower level equipped with pingpong/air hockey table, Art Gallery, music area with drums/guitars, sauna and much more!!