Vacation rentals in Callicoon Center

5 out of 5 average rating, 3 reviews

A modern dining area with a large wooden table and six wire chairs is illuminated by natural light from a large window. The space is complemented by a simple area rug and decorative plants, creating a serene atmosphere. A piece of floral artwork hangs on the wall.

Cabin in Roscoe

Callicoon Cottage

Welcome to Callicoon Cottage, a quiet & charming 2BR farmhouse in the Catskills, perfect for romantic getaways, friend gatherings and family adventures. Enjoy a modern kitchen, spacious dining, a deep soaking tub, a backyard fire pit and a creek. A 1-min walk to Callicoon Hills Resort offers dining, sauna, yoga, a pool, a gym & skating. Nearby towns of Callicoon, Livingston Manor & Jeffersonville offer restaurants, shopping, hiking & more. Family-friendly with crib, highchair & baby essentials.

4.89 out of 5 average rating, 118 reviews

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.

4.98 out of 5 average rating, 105 reviews

An outdoor fire pit area is surrounded by wooden Adirondack chairs, with a small table beside each chair. Soft lighting from torches highlights the natural stone circle and a rustic cabin stands in the background, partially obscured by trees under a twilight sky.

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!

4.99 out of 5 average rating, 186 reviews

Home in Bethel

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!

4.97 out of 5 average rating, 367 reviews

A cozy living room is highlighted by a dark green accent wall and wooden beams above. A comfortable sofa faces a wood-burning stove, with a large window allowing natural light. Two lounge chairs and a small coffee table create an inviting seating area.

Cabin in Callicoon

Chic Cabin on Callicoon Creek

***FEATURED IN ARCHITECTURAL DIGEST, TRAVEL & LEISURE, APARTMENT THERAPY, AND FODORS TRAVEL*** Set back on a small private road, this cabin dating back to the 1800s is perched above the Callicoon Creek, popular with fly fishermen casting for rainbow trout. Head up the wooded driveway and find yourself in a serene, green clearing all your own. The cabin and studio make for a peaceful getaway, shielded from the surroundings, but incredibly convenient for reaching nearby towns and activities.

4.99 out of 5 average rating, 135 reviews

Cabin in Roscoe

Wonder's Never Cease: Hot Tub, Sauna & Cold Plunge

Hi, I'm Wonder! Welcome to my magical Catskills cabin escape - quiet & with a private spa. Ideal for romantic getaways, vacations w family & friends, or wellness retreats. Nestled in nature, our clean log cabin offers a natural, chemical-free hot tub, sauna & cold plunge. Enjoy views from the porch, cozy by the wood stove, grill epic meals, indulge in the spa & explore hikes & cute towns. Child, infant, pet friendly. Helpful host! Book to reconnect with nature, one another & yourself.

4.93 out of 5 average rating, 140 reviews

A spacious deck is featured, surrounded by greenery and overlooking the hillside. Four bright red adirondack chairs are arranged for relaxation, and soft string lights hang above, creating an inviting outdoor space. A metal chiminea is positioned to one side, adding warmth.

Home in Livingston Manor

Parkston Schoolhouse

Relax and unwind in this historic converted one-room schoolhouse. Built in 1870, the Parkston Schoolhouse served all grade levels in the Livingston Manor area. The schoolhouse was retired and converted to a cozy cottage style home in the mid 20th century and has recently been renovated into a stylish tiny home getaway. The home is tucked into the hillside along the beautiful, winding Willowemoc Creek and is set amidst a lush Catskill landscape just a five minute drive from Livingston Manor.

Tiny home in Livingston Manor

The cabin is displayed at twilight, featuring a spacious wooden deck with a charcoal grill and a small outdoor dining set. Glass sliding doors invite views of the interior, which is warmly lit. Surrounding greenery adds a natural, tranquil touch to the setting.

4.97 out of 5 average rating, 124 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 countryside, you'll feel a world away from it all, yet still be just minutes from outdoor activities, thriving food scene, and Bethel Woods just 35 min away. Inside, you'll find a cozy queen bed, kitchenette, dining table, fast wifi, and a full bath. Outside, relax by the fire pit or cook up a meal on the charcoal grill. We are an LGBTQ+ inclusive space.

4.94 out of 5 average rating, 154 reviews

A restroom features a white toilet beside a window overlooking greenery. A small vase with a floral arrangement sits atop the toilet tank, while a patterned shower curtain adds a touch of color to the space.

Cabin in Walton

The Mill House: Creekside Catskills Spring Escape

Nestled in the heart of the Catskills and just a 2.5-hour drive from NYC, escape to a winter retreat where you can reconnect with nature and enjoy the serene beauty of the season. This historic gem underwent a meticulous restoration in 2021, marrying its saw mill heritage with contemporary luxuries, including a Nest thermostat, smart speakers, keyless entry, and fast wifi. Original exposed post and beam construction and Scandinavian-inspired design make for a unique and cozy atmosphere.

Cottage in Livingston Manor

A charming front porch features two rocking chairs positioned beside a small table. Potted yellow flowers add a touch of color, while a path leading to the entrance is framed by greenery and fallen leaves, evoking a welcoming outdoor space.

4.97 out of 5 average rating, 195 reviews

Catskills Cozy Retreat:Comfy Beds, Firepit, & More

Experience vintage charm at Jameson Cottage, a mid-century farmhouse-style home surrounded by nature. • Modern amenities and rustic wood finishes. • Gas grill and fire pit. • Two queen bedrooms, open living area, and full bathroom await. • Compact kitchen features beautiful cabinets and open shelves. • Relax in the living room or explore the backyard with its bountiful flora. • Embrace the amenities, unleash culinary creativity, and indulge in the luxury of a clawfoot tub.

4.97 out of 5 average rating, 207 reviews

The exterior of the contemporary home is showcased against a vibrant sunset, highlighting the rooflines and expansive windows. Lush green grass surrounds the house, leading to panoramic views of the distant mountains and valleys in the background.

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.

4.99 out of 5 average rating, 119 reviews

A set of wooden stairs leads downwards, framed by a rustic wooden railing with metal accents. Natural light filters in from a window at the base of the stairs, enhancing the warm tones of the wooden steps and surrounding wall.

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.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Callicoon Center vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Callicoon Center

5 out of 5 average rating, 3 reviews

A light-filled living area showcases large windows framing views of the outdoors. A cozy seating arrangement includes a spacious bench and a wooden table. A modern wood stove adds warmth, accompanied by soft textiles and indoor plants, enhancing the calming atmosphere.

Home in Livingston Manor

Livingston Manor Retreat

CharlieRating, 5 stars10 months ago

A beautiful home on a beautiful piece of land. A river runs through this property and you can hear it flowing all day. The house is beautiful and full of unique pieces. It feels like you’re staying at a friend’s house, not just an airbnb. We will stay here again!

4.95 out of 5 average rating, 94 reviews

A fire pit is surrounded by four wooden chairs, set against a snowy yard. The farmhouse is visible in the background, its windows glowing warmly at dusk. Trees frame the scene, showcasing the winter landscape.

Home in Jeffersonville

The Swiss Hill Farmhouse

RebeccaRating, 5 stars1 month ago

Great spot to get away and decompress for a weekend. Loved that it was dog friendly and my pup had a great time hanging out with us outside stress free because the property is at the end of the road. Hot tub was great in the evening after a hike and it was an easy walk into the town to get breakfast at the local bakery!

4.98 out of 5 average rating, 93 reviews

An expansive wrap-around deck features black outdoor furniture, including a dining table and several lounge chairs. Surrounding trees allow for a tranquil setting with views of the lake and hillside in the distance. Fallen leaves add a seasonal touch to the wooden flooring.

Home in Jeffersonville

The Nest At Swiss - Lakefront In The Catskills

SamRating, 5 stars2 weeks ago

We had an amazing weekend in the Catskills thanks to The Nest at Swiss. We brought five kids and 5 adults and we had the greatest time. Plenty of room to spread out while also a ton to do. We watched movies, played cards, made pop corn, built fires, smoked meat, went fishing, kayaking, played endless games of manhunt and monopoly. The Nest was set up for everything. We really enjoyed the short walks into Jeffersonville and hanging out on the decks. Even though the weather wasn’t perfect for Memorial Day weekend it did not matter to us. The Nest is also really close to Bethel Woods and we took him to concert on Saturday night super convenient location. The house was fully stocked and had everything we can think of. Well done Matthew!

4.64 out of 5 average rating, 14 reviews

An outdoor deck is surrounded by lush greenery, featuring a large dining table with seating for eight. Comfortable seating areas with gray cushions and a coffee table are positioned for relaxation. A barbecue grill and heating lamp are also visible, enhancing the outdoor living space.

Home in Roscoe

Modern House Deep in the Woods of Roscoe

CatherineRating, 5 stars5 days ago

My husband and I (along with our Golden Retriever Luna) had the fateful experience of staying in this dream of a home at the end of our honeymoon. We booked last minute hoping to extend our celebration just a day longer and it could not have been a better decision. This is by far one of the best places we’ve ever stayed (and we’ve traveled to some pretty cool places). It made you feel like you were tucked away in the mountains of Japan. The architecture alone is outstanding, the house is a true piece of art. It made us feel creatively inspired, at peace, and made our honeymoon celebration feel extra special. Even Luna felt right at home! We’re so grateful for our stay and will absolutely be back!

4.97 out of 5 average rating, 95 reviews

The kitchen features rustic stone walls complemented by warm wooden accents. A wooden bar counter with metal stools offers seating. Glassware is neatly arranged in a cabinet above, contributing to the charming atmosphere of the space.

Cabin in Jeffersonville

1930's Vintage Cabin · Hot Tub · Kohler Cabin

AlexandraRating, 5 stars5 days ago

This was a beautiful tranquil home with a cute town right down the road for local eats. We came to this area because of a race behind held at Bethel Arts Center. It was 15 minutes away and a perfect location. The home was spotless and so cozy!

4.97 out of 5 average rating, 71 reviews

Cabin in Youngsville

Cutbow Cabin Secluded Home near Livingston Manor

EricaRating, 5 stars2 weeks ago

Our second visit to Matt’s place was just as magical as the first, if not more so! It's the perfect place to immerse yourself in nature, offering a wonderfully isolated feel while still being conveniently close to quaint towns, great hikes and breweries. The light and the land surrounding the house are truly breathtaking, and we’re grateful it’s dog friendly. We absolutely loved our time here and can't wait to return.

4.96 out of 5 average rating, 24 reviews

A cascading waterfall flows down rocky cliffs, surrounded by lush greenery. Sunlight glistens on the water as it splashes into a shallow pool below. Two goats are seen near the water's edge, while a person relaxes nearby, enjoying the natural setting.

Hut in Roscoe

Roscoe Coop clucking crazy Hut

JenRating, 5 stars2 weeks ago

Debra’s place was great and just how she described. Debra was kind and helpful. She also offered us cold seltzer water when we arrived! I loved her friendly dogs too.