Holiday houses in Callicoon Center

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Top-rated holiday rentals in Callicoon Center

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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, 103 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

Guest favourite
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
4.9 out of 5 average rating, 157 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
The A-frame cabin is nestled among trees, featuring a wooden deck and wide glass doors that open to the interior. A private hot tub is positioned nearby, providing a relaxing outdoor space surrounded by nature.
Cabin in Damascus
5 out of 5 average rating, 226 reviews

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.

Top Guest favourite
The sunken living room features a mix of modern furnishings, including a cozy sofa and an iconic lounge chair. Large windows provide natural light, showcasing the wood-beamed ceiling and a stone fireplace with a stacked wood supply nearby.
Home in Liberty
4.99 out of 5 average rating, 121 reviews

Stone Creek House: A Tranquil Family Getaway

Welcome to Stone Creek House, a creekside dog-friendly family retreat. Minutes to Livingston Manor, our light-filled house is designed for gatherings and relaxation. The house has a private creek with a small swimming hole and game room on three acres of landscaped property. A two-sided fireplace keeps you cozy in the living and dining rooms, while the outdoors has a private deck with a chimenea, swing, a field for activities, a fire pit, and a large grill for cooking. photos @stonecreekhouse

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
4.97 out of 5 average rating, 118 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
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.
Cabin in Jeffersonville
4.98 out of 5 average rating, 252 reviews

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!

Guest favourite
Cabin in Jeffersonville
4.96 out of 5 average rating, 136 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.

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
4.9 out of 5 average rating, 194 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.

Guest favourite
A modern cabin exterior is displayed, featuring a wooden facade and large windows. Snow blankets the ground, and a riverside view provides a peaceful backdrop. A deck leads to the river, surrounded by bare trees, creating a serene winter environment.
Cabin in Livingston Manor
4.95 out of 5 average rating, 117 reviews

Private riverside cabin with soaring ceilings

Newly built riverside cabin overlooking 600ft of private riverfront right on the edge of Livingston Manor. The cabin soaring ceilings and large windows create a light filled space and big views onto the Willowemoc river - stroll down the bank to fly fish one of the areas most famous rivers, or just enjoy looking out over it from your own private deck. After sunset enjoy the outdoor firepit, or indoor stone clad fireplace, or cook a feast from the chef's kitchen.

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, 138 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.

Top Guest favourite
A one-story cabin is surrounded by green grass and trees displaying autumn foliage. The structure features a white exterior with a sloped roof and two symmetrical doors on its lower front. A small window allows natural light into the space, blending harmoniously with the tranquil rural setting.
Guesthouse in Roscoe
4.99 out of 5 average rating, 133 reviews

Map Maker's Cabin

All season private, cozy cabin in a peaceful woodsy oasis, 15 min from Delaware River; off a main road and close to many peaceful walks. Fast wifi for working remotely, writer's retreat, romantic getaway, meditation, yoga, or time in nature. **We have an (inflatable) hot tub which we fill for guests (unless temps are way too low). NOTE: all-wheel/four wheel drive is highly recommended during winter months. We are looking forward to hosting you!

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, 213 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-Oct.

Popular amenities for Callicoon Center holiday rentals