Holiday rentals in Callicoon Center

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Top-rated holiday rentals in Callicoon Center

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A cozy living area features large windows offering views of the surrounding woods. The space includes a plush light grey sofa, black accent chairs, and a wooden coffee table. A warm-toned rug and soft, textured cushions add comfort to the ambiance.
Cabin in Livingston Manor
4.98 out of 5 average rating, 110 reviews

The Ensconce: Modern cabin in the woods

Our cabin is a stylish retreat set on 5 wooded acres. Just 2 hours from Manhattan, the home is 12 min from LManor, where you can enjoy a day in nature and venture out to NYC-quality restaurants and breweries in the evening. There is also great access to hiking, fly fishing, and snow sports. Our newly built, air-conditioned home has vaulted ceilings, bright sunlight, designer furniture, and forest views. Enjoy the deck for dining or watching the moonrise. Contact us for longer than 11-day pricing

Superhost
An indoor heated pool area features large windows allowing natural light to fill the space. Surrounding the pool are loungers, a colorful floating swan, and a bright orange inflatable, creating a cheerful atmosphere. Wood paneling and a beamed ceiling complete the inviting setting.
Home in North Branch
4.89 out of 5 average rating, 175 reviews

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

Top guest favourite
A charming cabin with a dark exterior and bright yellow door is surrounded by lush greenery. A dog is seen standing on the grassy area in front, with a deck and fire pit visible nearby. Stacked wood is neatly arranged to the side of the cabin.
Cabin in Roscoe
4.98 out of 5 average rating, 121 reviews

Cabin@Crow Hill: unplug and reconnect with nature

Escape it all, listen to the birds and near by Buck Brook. Explore the Catskills with plenty of hiking, lakes, and fly fishing. The stars are incredible, so as you sit on the balcony or at the fire pit look up. Crow Hill is located on a quiet road away from the bustle of town. The wifi is moderate due to the location, so it allows you to unplug. Crow Hill is dog friendly ( no cats) and perfect for a family getaway. The cabin is deep cleaned and sanitized between guests. Come take a break!

Guest favourite
Cottage in Livingston Manor
4.97 out of 5 average rating, 227 reviews

Charming Cottage~Bethel Woods Concerts~Firepit

Stylishly designed mid-century cottage surrounded by nature • Livingston Manor 12 min, Bethel Woods Center for the Arts 17 min. • Great for couples or small families • Walnut Mt. hiking 8 min. • Gas grill & fire pit • Rocking chair front porch • 2 queen bedrooms, open living area, 1 bathroom. • Fully-stocked kitchen/beautiful cabinets and open shelves. • Relax inside or explore the backyard's natural beauty. • Indulge in the luxury of a clawfoot tub. You'll love it! Book with us now!

Guest favourite
Cabin in Jeffersonville
4.94 out of 5 average rating, 144 reviews

1930's Vintage Cabin · Hot Tub · Kohler Cabin

Escape to Kohler Cabin in Jeffersonville A Rustic Retreat with Modern Comforts Discover the charm of Kohler Cabin, a vintage-inspired retreat nestled in the heart of Jeffersonville. With four bedrooms and two full baths, this cabin offers a unique blend of rustic elegance and modern convenience, perfect for a memorable getaway. Relax and rejuvenate in the screened-in hot tub, enjoy outdoor dining in the fenced-in yard, or simply unwind amidst the tranquil mountain views.

Guest favourite
Chalet in Obernburg
4.97 out of 5 average rating, 245 reviews

King Of The Hill

Romantic Mountain Top Retreat with Million Dollar Views Escape to this incredibly private, mountaintop vacation home, nestled on 80 acres of pristine land. Offering breathtaking, panoramic views. This peaceful retreat is the perfect getaway for relaxation and romance. Just 2 hours from the GW Bridge, enjoy the tranquility of nature without sacrificing modern comforts, including high-speed internet service. The ideal escape for those seeking both privacy and convenience.

Top guest favourite
A spacious great room features exposed wooden beams and warm wood flooring. In the center, a wood burning stove provides warmth, surrounded by several seating options including rocking chairs and a dining table. Large windows allow natural light to fill the space.
Home in Livingston Manor
4.91 out of 5 average rating, 203 reviews

Butternut Farm Cottage

Butternut Farm Cottage is an 1880's farmhouse. One and a half story great room with wood burning stove, kitchen, dishwasher; laundry room, two bathrooms and library with TV and Wifi. Lots of natural light. Sound system throughout. Covered porch. Comfortable beds. BBQ grill and fire-pit. Good for couples, solo adventurers, business travelers, families, and medium size groups (up to 6). **While not an issue for most some ambient noise from Rt. 17 is heard when outside.

Top guest favourite
An inviting living area features a stone fireplace, flanked by large windows that provide scenic views. A combination of leather and fabric seating enhances comfort, while a rustic wooden coffee table sits at the center. Natural light fills the space, creating a warm atmosphere.
Chalet in North Branch
4.99 out of 5 average rating, 143 reviews

Catskills Mountain Chalet l 5 Star experience !

Stylish Chalet in the world famous Catskill mountains privately tucked away on 12 acres surrounded by wildlife and nature. Year-round outdoor activities, fine dining, breweries, and boutique shopping all nearby. Enjoy it all here at Clover Fields! Why "Clover Fields" you ask? Deer visit our property almost daily to graze on our sweet clover fields. It's not uncommon to see them throughout the day. Other notable guests: fox, various birds, woodchucks, chipmunks.

Guest favourite
A rustic cabin is nestled among lush trees, featuring a metal roof and warm, inviting windows. Soft lighting from the windows enhances the natural surroundings, while a stone walkway leads to the entrance, blending harmoniously with the forest landscape.
Place to stay in Downsville
4.88 out of 5 average rating, 234 reviews

Half Moon: Fairytale Catskills Retreat

Enjoy nature in style at this fairytale in the forest. This idyllic escape combines whimsical structures, curated gathering spaces and a private wooded hillside surrounded by hiking trails and quaint towns. Disclaimer: This is a rustic cabin. Heating is from a wood-burning stove, there is no AC. The bath house is a separate structure from the cabin, up a hillside with stone steps. Cooking is via charcoal grills, small outdoor kitchenette or fire.

Top guest favourite
The exterior of the modern structure features large windows and a sloped roof. A wooden deck is highlighted with two red chairs and decorative planters filled with greenery and flowers. Soft sunlight illuminates the space surrounded by trees.
Guest house in Callicoon
5 out of 5 average rating, 108 reviews

R52Creekside one bedroom cottage

NEW Construction! Centrally located to all Sullivan county has to offer! Bethel woods, Livingston Manor, Callicoon and much more close by! Walk to a great little local deli and drive to many close restaurants. Set up for two adults or two adults with one small child. Efficiency kitchen (no oven). Ten acres with a creek and lots of area to walk and have a dog. King bed sleeping loft! Great area to explore in summer and winter! Dogs welcome!

Top guest favourite
A serene cabin is situated next to a tranquil pond, reflecting the surrounding greenery. The dock extends into the water, offering a peaceful outdoor space. The area features a well-maintained lawn with tall grasses, enhancing the natural setting.
Cabin in Callicoon
4.99 out of 5 average rating, 219 reviews

The Cabin at Pleasant Valley Farm

The cabin is located on a dirt road on our farm with a beautiful pond and an amazing view! This off-grid, cabin has two queen beds (100% cotton sheets), a mini-kitchen with a battery-ignition gas range, solar powered refrigerator, solar lighting, a wood stove, an outdoor shower, a fire pit, and an old-fashioned outhouse. An expansive porch and dock provide comfortable outdoor living. A seasonal favorite, the cabin is available May-Sept.

Guest favourite
Two alpacas are seen in the foreground, highlighting the rural setting. In the background, the barn's upper structure features dual cupolas and a spacious deck. Soft morning light enhances the natural landscape, while a satellite dish is visible on the barn's side.
Barn in Roscoe
4.98 out of 5 average rating, 150 reviews

Sleep Above the Alpacas Scenic Farm Getaway

Slumber comfortably atop our 100+ alpacas, Angora rabbits, chickens and potbelly pig named Daisy. BuckBrook Alpacas offers a 3-bedroom loft apartment rental above our barn. You will sleep surrounded by the mountains and the animals on one of the highest peaks of the county. Wake up for a complimentary farm tour and enjoy a 10% off shopping pass in our farm store on our entire selection of alpaca gifts for the whole family.

Popular amenities for Callicoon Center holiday rentals