Family-friendly holiday rentals in Callicoon

Mountain View Apartment

We offer a quiet and extremely clean place. We are only 6 miles from Belleayre Mtn Ski Center. Restaurants are nearby. You’ll love our place because of the neighborhood, the outdoors space, the light, and the kitchen. Our place is good for couples, solo adventurers, and business travelers. WIFI is 300mbps. We have security cameras outside only, EV Charging station on the property. We now have an outdoor fire pit (wood not included). We also have a standby generator in case of a power failure.

Catskills Retreat: Hot Tub | Fireplace | Firepit

Year-Round Catskills Retreat Escape to Five Star Cottage in Windham, NY, just 2 hours from NYC. This spacious 4-bedroom, 2.5-bath home features stunning mountain views, a cozy wood-burning fireplace, a hot tub, and a large deck for year-round enjoyment. Ski in the winter, and explore nearby hiking trails, lakes, and waterfalls in the warmer months. Ideal for families and groups seeking adventure, wellness, or a peaceful retreat. Book your stay today and experience the beauty of the Catskills!

Waterfront, outdoor deck with fire pit

Enjoy the fresh mountain air and relaxing vibe hosted by Mother Nature herself. Located on Main St. in Hunter - 3 min walk from the bus stop, 8 min walk to Hunter Mt if you choose (2 min drive w. Car/ski equipment) Cozy and comfortable house that overlooks Hunter Mountain. Private waterfront access to the Schoharie creek, good sized sunken backyard w fire, upper and lower patios - Sleeps 6 in beds, 2 more on the sofa bed. 2 full baths, washer and dryer, wifi and Smart Tv's with built in Roku

"Cabinessence" on Greenwood Lake, 60 mi from NYC

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Enchanted Castle - Unique & Charming Getaway

Recently renovated unique Harry Potter inspired 4BR/2BA 1600sq ft castle themed home near Kalahari, Mt Airy Casino & Camelback! Enjoy a private fenced yard with Hot Tub, Sauna, Fire Pit, Mini Golf, Swing Set, Patio & BBQ Grill. Inside: Pool Table, Ping-Pong, Chess, Scavenger hunt, Smart TVs, WiFi, Netflix & Family Games. Perfect Poconos getaway with comfort & fun for all ages—very close to top attractions, skiing, waterparks & dining. Great for families, couples & group retreats.

LUX Lakefront, HotTub, Pool, Pickleball, Game Room

Olibear is the perfect spring retreat for couples, families, or anyone craving a lakefront getaway. Situated by the water, our home blends cozy charm with the blooming Pocono scenery. Only 5 minutes from Bushkill Falls, discover vibrant spring sights or unwind by the indoor community pool, open weekends from 12-4 PM. Relax in the private hot tub, paddle kayaks or canoes, wander lively trails, or enjoy the firepit beneath the spring sky. Secure your spring getaway today!

Peaceful Cabins by the river, excellent wifi!

Just figured out availability for our cabins this summer! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” and super chic Inness.

Nicks Place

Open space kitchen, dining, and living room All in a cozy country setting . Two bedrooms with queen beds and two single beds in spacious loft. Bright and sunny. Outdoor grille, firepit, and sun porch. Close to hiking trails, one mile from state gamelands. Minutes from Beaverkill and Willowemoc rivers. Close to three local breweries and distillery. Within an hour of ski resorts. Super quiet location, off the beaten path.

LAKE DAYS are the BEST!

Township Registration # 006914” Welcome to our shareable happy place in the heart of the peaceful Pocono Lake. The lake with swimming beach and playground is our backyard LITERALLY! Located in Locust Lake at pines lake where you can just grab our canoe & go for a nice fishing trip at the end of the day the kids gets entertained all day. We provide basically everything you could possibly need for your best vocation