Vacation rentals in Cuddebackville

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Top-rated vacation rentals in Cuddebackville

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Top guest favorite

Cabin in Cuddebackville

5 out of 5 average rating, 9 reviews

Cozy Mountaintop Cabin

Rustic and inviting mountain cabin located on 100 acres of private property. Relax and enjoy the peaceful surroundings only 2 hours from NYC. Perfect place for a romantic getaway or family fun. Breathe in the fresh mountain air, enjoy s’mores at sunset sitting around the firepit, just sit and relax and enjoy the sounds of nature and the chirping of hummingbirds, take a walk and bird watch 2 Bedroom cabin Sleeps 5 Upstairs 2 queens beds Downstairs bed - bunk beds Pullout couch in living room

Guest favorite

Cabin in Wurtsboro

4.97 out of 5 average rating, 354 reviews

Summer 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.

Top guest favorite

Cabin in Millrift

4.99 out of 5 average rating, 236 reviews

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.

Superhost

Place to stay in Cuddebackville

4.76 out of 5 average rating, 191 reviews

Welcome to your twelve-sided getaway!

Welcome to @cabin_dodeca ! Cabin Dodeca is a twelve-sided retreat located in Cuddebackville, New York. This is the upgraded cabin experience for anyone looking to detach and unwind from busy life. Cell service is minimal/non-existent however there is WiFi which allows streaming but can be slow. Utilize the large, 360-degree wraparound deck to enjoy the outdoors, cozy up in the screened-in porch, or stay inside in either living space. And pets stay for FREE We look forward to hosting you!

Guest favorite

Guest suite in Chester

4.96 out of 5 average rating, 341 reviews

Adorable Guest Apartment in Victorian Mansion

This lovely 3rd floor private apartment is in an 1883 Victorian Mansion in Blooming Grove, NY for 1 - 6 people. It is beautifully furnished, has luxurious beds, so let us know if you need one, two or three bedrooms! The apartment has a private entrance, a claw foot tub, French door shower, and a kitchenette with sunny breakfast nook. It's freshly renovated and spacious. You will have to take 2 staircases. Our land has a nice view of a field of wildflowers, and our neighbor has cows.

Guest favorite

Cabin in Rock Hill

4.88 out of 5 average rating, 397 reviews

Trails Head Cabin

Welcome to Trails Head Cabin! Located on a quiet dead end road, this cabin sits at the head of the Neversink River unique area and offers activities such as hiking, fishing and hunting. My wife and I have fully renovated the inside of the cabin, and have begun to update the exterior. A five minute drive to Resorts World Casino and Holiday Mountain Ski and Fun Park. A twenty-five minute drive to Bethel Woods Center for the Arts (sight of the 1969 Woodstock Festival). See you soon!

Top guest favorite

Cabin in Cuddebackville

4.99 out of 5 average rating, 152 reviews

Sauna & Hot Tub Creekfront Oasis · Hikers Hollow

Tucked away in the small town of Cuddebackville, you will find a wonderful rough cut cabin with all the comforts and amenities for a relaxing stay. The cabin is situated on 3+ acres on a quiet dead end road with very minimal car activity. Enjoy the wonderful nature that surrounds you, with the calming sound of the stream in the background. The interior of the cabin has been updated to ensure an exceptionally comfortable stay while still holding true to its original 1940's charm.

Guest favorite

Cottage in Goshen

4.92 out of 5 average rating, 341 reviews

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Picture this... You escape to a relaxing, picturesque, and peaceful country cottage and enjoy some of your favorite convenience amenities like 1 Gig Wifi and your favorite streaming sources. Just 10 minutes to LEGOLAND, 3 miles to the famous Orange Heritage Trail, and less than 20 minutes to America's oldest winery, Brotherhood, this cottage has something to offer for everyone. You'll be minutes from conveniences like Target but taking in the views, you'd never know it.

Guest favorite

Camper/RV in Godeffroy

4.9 out of 5 average rating, 21 reviews

Sydney, the Cozy Place Near the River

Unplug in Sydney. If you're looking for a peaceful escape to reconnect with nature and simplicity, "Sydney"- the RV offers the perfect cozy retreat. The Neversink River, located just across the street, is a great place to spot bald eagles nesting or enjoy fishing. You can also bike, swim, hike, or explore the area's rich history. This charming RV is more than just a place to stay—it's an invitation to slow down, breathe deeply, and experience life at a gentler pace.

Top guest favorite

Cabin in Sparrow Bush

5 out of 5 average rating, 36 reviews

Forest cabin escape | Pickleball court & fire pit

Welcome to your private escape in the heart of nature. Nestled on a 17-acre property, this newly renovated (2025) mezzanine cabin blends modern luxury with wilderness charm. Whether you're seeking a romantic getaway, a solo retreat, a digital detox, or an adventure-packed escape, this is the place for you. Get active in the forest and on the pickleball court, work remotely with a view, and then wind down with a book, a meal, or a movie—your perfect escape awaits!

Top guest favorite

Tiny home in Cuddebackville

5 out of 5 average rating, 108 reviews

The Silo-a tiny house getaway in the Catskills

No Winter Blues here! THE SILO-UNIQUE AIRBNB!!! Formerly 1920's feed Silo. Close to Holiday Mountain Ski, BETHEL WOODS Museum, Hike/bike 52 miles of local trails, brewery/winery, casino & unwind! This 4 flr. + loft silo nestled in Catskills w/ stunning views. Attached to early 1900’s barn-owners on-site. See guidebook for local suggestions. The main house barn is NOT the airbnb/rental. The Silo is the airbnb

Guest favorite

Cottage in Sparrow Bush

4.93 out of 5 average rating, 183 reviews

Serene Lakeside Oasis - 1.5 hrs from NYC Fast WiFi

Surrender your stresses at our "Serene Lakeside Oasis", a tranquil cottage nestled between a forest and a lake. Here, the beauty of the outdoors seamlessly blends with homely comforts. Whether you're working remotely, indulging in a day of rest, meditating by the water, or simply observing the local wildlife against the lake's scenic backdrop, this oasis offers unparalleled serenity.