Vacation rentals in Callicoon Center

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Top-rated vacation rentals in Callicoon Center

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

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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

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.

4.89 out of 5 average rating, 181 reviews

Guest favorite

Cabin in Roscoe

Wonders Never Cease: Peaceful Cabin with Wow Spa

Welcome to Wonders Never Cease, my upscale log cabin sanctuary & private spa, perched on a hilltop amid 12 acres of forest, with a spring-fed pond, incredible stargazing & your own hot tub, cold plunge and sauna. Ideal for romantic getaways, family vacations, trips with friends, wellness retreats - anyone craving a reset in nature. Wonders Never Cease is far more than a typical Airbnb cabin. It’s a destination in itself—and 1 in 5 bookings are returning guests. We love hosting, and it shows!

4.99 out of 5 average rating, 184 reviews

Top guest favorite

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

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!

4.98 out of 5 average rating, 123 reviews

Top guest favorite

Two kayaks, colored yellow and orange, rest on the grassy shore of a serene lake. A small dock extends into the calm water, reflecting the colors of a sunset sky. Trees line the horizon, completing the tranquil lakeside setting.

Cottage in Livingston Manor

Gorgeous Waterfront w/ Hot Tub and Game Level

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to The Glass House! Here are a few things I think you’ll especially enjoy about the house. Highlights – You’ll love the: Peaceful waterfront setting – tucked away on the lake, yet just minutes to town Year-round hot tub – the perfect way to unwind after hiking, or exploring Family-perfect layout – two spacious levels with a game/media room and screened porch Kayaks & life vests – easy, safe access to the water for all ages

5.0 out of 5 average rating, 110 reviews

Guest favorite

The rustic cabin, crafted from dark wood, is set against a colorful sunset sky. A gentle slope reveals steps leading up to the main entrance, while a green patio umbrella shelters a seating area nearby. Surrounding greenery adds to the natural ambiance.

Guesthouse in Callicoon Center

Beautiful Mtn Cozy Cabin-183 acres-Amazing Views

Bethel Woods & Callicoon Hills so near. Truly beautiful mountain cabin. Artistic, eclectic, luxurious—hi-speed internet—private patio & picnic table—comfy beds, bathrooms with 2 person Jacuzzi tubs—house-wide stereo—induction cooking–air-fryer/oven—dishwasher— linens–snacks-drinks included. Geothermal heat/hot water, solar electric — EV charging. Private chef and masseuse available. Farm-to-table restaurants, skiing, hiking, bike rentals, tons of trails, fishing and 183 acres to explore!

4.97 out of 5 average rating, 65 reviews

Top guest favorite

The exterior of a charming black home is illuminated by soft yellow lights from the windows at dusk. A stone path leads through a landscaped garden area, which is bordered by planters. Multiple light sources create a serene atmosphere amidst the surrounding greenery.

Chalet in Callicoon Center

Architecturally Unique Catskill Chalet

Unwind in a secluded upstate escape on 6+ wooded acres off a dead-end road while relaxing to the sound of Callicoon Creek. This newly renovated and thoughtfully designed home has multiple lounging areas, a wood-burning fireplace, hot tub, and fire pit. We are less than 15 minutes from the most charming Catskill Main Streets of Livingston Manor, Roscoe, Jeffersonville, and Callicoon and a five-minute walk to Callicoon Hills for dinner or coffee. Bring your family + dog out to the country!

4.99 out of 5 average rating, 91 reviews

Top guest favorite

A cozy living area is highlighted by large windows allowing natural light to fill the space. A wood-burning stove serves as a focal point, with a plush sofa draped in a soft throw. A mix of plants and decorative items enhances the inviting atmosphere.

Chalet in Roscoe

Sunday Mountain House - Cozy Catskills Chalet

Sunday Lodge & Mountain House is a peaceful retreat on 5 acres in the Catskill Mountains. Our home is located about 2-2.5 hours from NYC, and minutes from the charming towns of Roscoe and Livingston Manor. Tucked away on a mountain road, this is the perfect a place to relax and unwind. You can sleep. You can sip. You can cook. You can workout. You can hang. Outside of our doors you can fish. You can hike. You can stargaze. You can play. A place to do everything or nothing at all.

4.96 out of 5 average rating, 161 reviews

Top guest favorite

Chalet in Obernburg

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.

4.97 out of 5 average rating, 250 reviews

Top guest favorite

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

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.

4.99 out of 5 average rating, 149 reviews

Top guest favorite

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.

Guesthouse in Callicoon

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!

5.0 out of 5 average rating, 109 reviews

Guest favorite

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

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.

4.98 out of 5 average rating, 151 reviews

Superhost

Home in Callicoon Center

Lilac Hill - VIEWS, Privacy, and Design

Lilac Hill is a stunning escape in the heart of the Catskills, located just 2 hours from NYC. Set on 39 private acres with charming views of the Callicoon hills, surrounded by woodlands, the home has 4 bedrooms and 3 luxe baths and is a recently renovated, design-lover's dream. Amenities include a fireplace, firepit, and access to the best hiking and dining in the region.

4.78 out of 5 average rating, 18 reviews