Family-friendly vacation rentals in Callicoon

Swimming Hole, OMG Game Barn! Hot Tub

10% discount on 3 night stays! 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 on the property! Cross one creek into a 7 acre forest oasis. FAST WiFi, Hot Tub, Firepit, grill, Deck. Callicoon has shops, restaurants and Delaware River access. Seminary Hill 5 min. Villa Roma 9 min (skiing, tubing). We're renovated, clean and stocked with a barn like no other!

Indoor spaces · Kitchen · 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.

Family · Indoor spaces · Hiking

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 · Family · Cleanliness

Cozy Cottage in Popular Narrowsburg

A sweet cottage in the artsy hamlet of Narrowsburg welcomes you for a quiet retreat in the country. Moments from the Delaware River and the village, spend hours taking in the serenity of the river and rolling hills of the surrounding countryside, or popping into town for arts and entertainment. There are two separate bedrooms, one with a queen bed and one with a full bed; a well-equipped kitchen; WiFi; a front and back porch; and a deck Come enjoy the all-season splendor of Sullivan County

Indoor spaces · Family · Hiking

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.

Indoor spaces · Kitchen · Decor

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.

Kitchen · Indoor spaces · Solo travel

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 · Family · Wifi

Mid-Century Cottage | Lovely Yard | Fast Wifi

Stylishly designed mid-century retreat surrounded by nature • Livingston Manor & Jeffersonville 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. •. Enjoy fast internet Your unique escape awaits!

Kitchen · Family · Value

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

Perched on a hill with fantastic views, this modern 3BR/2BA Catskills retreat is perfect for couples or small groups. Unwind in the hot tub, cozy up by the indoor fireplace, make s'mores by the outdoor fire-pit, or enjoy your evening cocktail by the additional gas fire-pit on the patio. Watch deer wander through the meadow, enjoy a game of ping-pong or darts. House offers stylish interiors and premium bedding. Check out our guide-book for activities in the area.

Kitchen · Indoor spaces · Breakfast

Delaware River retreat

Approximately two hours from the GW bridge - this beautiful country home is located directly on the Delaware River. The house features a full kitchen, a large dining room, and two porches that overlook the river. Watch the eagles, warm up by the fireplace, ski, hike, fish, canoe, swim, eat and laze about. With hi-speed cable and WiFi, tons of space inside and out, this house is perfect for a getaway, staycation, or for families and couples looking to remote-work.

Kitchen · Indoor spaces · Hospitality

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.

Indoor spaces · Family · View

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.

Family · Kitchen · Check-in