Vacation rentals in Callicoon Center

Treetop deck, hot tub, and chef's kitchen

Welcome to our spacious, pet-friendly 1960s home tucked away on 5.5 private acres - just mins from two of the most popular towns in the Sullivan Catskills: Roscoe and Livingston. This bright 4 bed/3 ½ bath home works great for a couple or a crowd with plenty of indoor and outdoor space to gather or spread out. There’s a dreamy (and VERY well-stocked) kitchen. Two living rooms are perfect for leisure or work-from-home needs, and the home is stocked for visiting families. Deluxe 6-person hot tub!

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.

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!

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!

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 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, coffee, or the pool. Bring your family + dog out to the country!

Secluded oasis nestled in nature

Relax at our secluded oasis in the Catskills and explore over 12 acres of woods & lawn to play in. Hang out in our recently restored barn, featuring basketball hoops, a ping pong table, darts, and a place for your yoga or work-out routine. Relax in the hammock watching your kids on the trampoline or take the whole family on a day trip to near-by swimming holes, fishing, day-hikes, farmer markets, or other adventures. Finish the day around the campfire, eating S'mores under the stars.

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! We allow dogs but not cats due to allergy issues!

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.

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.

Spacious Catskills Farmhouse w/Private Pond

Welcome to Hillside House! Beautifully renovated, Hillside is a spacious farmhouse nestled on 10 secluded acres in the Catskill Mountains. With 7 bedrooms, 6 bathrooms and plenty of spaces to gather, this historic home is perfect for group getaways, family vacations and anyone looking to soak in the countryside. Relax on the grounds' mountain meadows and private pond, or explore some of the areas best cafes, vintage shops and restaurants.

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.

Hust Haus | Sweeping Catskills Views on 20 Acres

Hust Haus is a modern two bedroom retreat set on 20 private acres with incredible sweeping views of the Catskills. Wander the property along a seasonal stream, gather around the Solo Stove, or relax on the patio and take in the scenery. Inside, enjoy radiant heated floors, a fully stocked kitchen, and thoughtful modern comforts, all surrounded by the peaceful countryside of Jeffersonville.