Family-friendly holiday rentals in Callicoon

Catskills Cottage w/ Hot Tub & View

Recharge in the secluded garden hot tub at this charming 1900s farm cottage and take in charming country views. Soak up the contemporary, Scandinavian-style interiors, then toast marshmallows around the fire pit under the stars. This cozy 1100 SF home is a perfect getaway to unwind, located just two hours from Manhattan. *Note for Airbnb Guests* You may have noticed increased prices which is due to Airbnb shifting the service fees entirely onto Hosts, instead of split between Hosts and Guests.

Family · Indoor spaces · Wi-Fi

The Schoolhouse at Kenoza Lake

The Schoolhouse at Kenoza Lake. This late 1800's renovated schoolhouse is the perfect getaway. Only a 2 hour drive from NYC. Old world charm with modern finishes. House features one bedroom plus a sleeping loft, a total of 3 beds plus a bunk bed, claw foot tub, cast iron wood stove, dinner barn, sleeping loft, vegetable garden, outdoor fire pit with bistro lights and Adirondack chairs. 10-20 min driving distance to all of Sullivan County's culinary offerings. 7 min drive to grocery store.

Indoor spaces · Kitchen · Check-in

Luxury Historic School House Cottage

Step into history inside our freshly renovated 1800s school house home. Relax and take it easy on the expansive front porch, with sweeping views of rural farmland and a historic cemetery next door. Sit by the fire and enjoy a book or beverage with friends and family and cook a nice farmhouse meal. This unique and tranquil getaway won't disappoint. And it's just 4 minutes from Narrowsburg's Main Street. Swimming holes and hiking trails along the Delaware River are just a stone's throw away.

Family · Kitchen · Sleep quality

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.

Family · Kitchen · Breakfast

Swimming Hole, OMG Game Barn! Hot Tub

Swimming hole in Callicoon Creek! 3,500 sq ft OMG Barn with 3 floors of fun: games, lounge, playground, billiards...! Stunning water views year-round. Excellent trout fishing. Two creeks merge together on the property. Cross the side creek into a forest oasis with 7 acres of nature trails. Callicoon has shops, restaurants and Delaware River access. FAST WiFi, Hot Tub, Firepit, Gas grill, Deck. 5 min to Seminary Hill. Villa Roma 9 minutes (skiing, tubing). We're renovated, clean and stocked.

Family · Indoor spaces · Comfort

3BR/2BA • Private Pool & Hot Tub Near Bethel Woods

A modern 3BR/2BA Catskills retreat with a private pool, hot-tub and fireplace. 10 mins away from Narrowsburg's shops and restaurants as well as Delaware River access for swimming and hiking. 15 mins to Bethel Concerts. Perched on a hill, offering scenic views and serenity- a true getaway destination. Enjoy modern decor, premium bedding, AC, fast Wi-Fi, and purest water that you’ll find. Swim, grill, play ping-pong, darts, star gaze. Pool season ends 9/14th. Hot tub is always open.

Family · Kitchen · Walkability

Chez Cochecton, a modern cabin in the Catskills

Completely renovated inside and out. This unique cabin style home is built for style and comfort. You'll love the thoughtful design and finishing touches. Enjoy some music and wine while relaxing in the private backyard. Cochecton and neighboring towns of Callicoon and Narrowsburg are full of amazing restaurants, shops and hangouts. Situated just off the Delaware River, this home is very close to swimming, hiking, and kayaking. Enjoy all the beautiful Catskills have to offer all year long!

Kitchen · Indoor spaces · Bathroom

Dog friendly, heated pool & Hot Tub w/ fenced yard

Escape to a modern mini barn 7 mins from Narrowsburg with a heated pool, hot tub, fire pit, high-speed Wi-Fi, Ev charger, backup generator and a fully fenced yard for your pups! Set in the gorgeous Hamlet town of Narrowsburg, my home is a 5 min drive into Narrowsburg Main Street! Bethel, Callicoon, Barryville, Livingston manor, are all 25 mins away. If you're looking to ski Big BEAR Mountain is close by! High speed internet 500mps. 7 day bookings and monthly bookings receive discounts!

Indoor spaces · Kitchen · Laundry

Close to Cute Towns~Labor Day~Firepit

Stylishly designed mid-century cottage surrounded by nature • Livingston Manor 12 min, Bethel Woods Center for the Arts 17 min. • Great for couples or small families • Walnut Mt. hiking 8 min. • Gas grill & fire pit • Rocking chair front porch • 2 queen bedrooms, open living area, 1 bathroom. • Fully-stocked kitchen/beautiful cabinets and open shelves. • Relax inside or explore the backyard's natural beauty. • Indulge in the luxury of a clawfoot tub. You'll love it! Book with us now!

Indoor spaces · Kitchen · Checkout

Hilltop Farm Campsite 20 mins to Bethel Woods

98 year 3rd generation family farm. Located 4 miles from scenic Delaware River. Only 20 mins from Bethel Woods! Very scenic peaceful and quiet. Multiple basic camp sights available, two different hilltop peaks with extraordinary views. Creeks, springs, hiking opportunities on two 100 acre parcels. Cows pigs and poultry live at the lower farm year round while hay is made at the upper farm come warm summer days. Wildlife abounds at the farm. Come have a peaceful stay on the hill!

Family · Value · Cleanliness

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.

Family · Indoor spaces · Outdoor spaces

Private Riverfront Catskills Retreat w/ Hot Tub

Tucked away on a private stretch of riverfront in the western Catskills, this cabin was made for unforgettable summer days. Morning coffee on the deck, afternoons by the river, golden-hour dinners outdoors, and fires under the stars. Inside, expansive picture windows, warm mid-century interiors, and thoughtful details create a space that's equal parts design-forward and deeply relaxing. Perfect for couples, families, friends, and dogs.

Indoor spaces · Family · Accuracy