A rural landscape with a house surrounded by autumn-colored trees and rolling hills.

Callicoon Hotel Guide - Family Friendly Hotels in Callicoon, New York

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Check availability on Callicoon Family Friendly Hotels

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Callicoon family-friendly hotels

A water park with a water play structure and people enjoying the water.
A hotel lobby with round tables, cushioned chairs, a large pillar, and a projection screen displaying a movie.
A hotel reception area with a wooden reception desk, multiple computer monitors, and a large chandelier.
A wooden building with a staircase leading to a balcony, surrounded by snow and trees.

1. Villa Roma Resort and Conference Center

Villa Roma Resort and Conference Center
Callicoon
  • All-day family adventures at this ski resort with an 18-hole golf course, indoor and outdoor pools, and waterslide fun.
€159
includes taxes & fees
12 Oct - 13 Oct
Villa Roma Resort and Conference Center
A wooden deck with Adirondack chairs and a small table, overlooking a garden.
A modern kitchen with a central island, stainless steel appliances, and wooden shelves.
A modern wooden house with a deck, large windows, and a separate black section.
A modern bathroom with a freestanding bathtub, a glass shower enclosure, and a window with wooden blinds.

2. Bright Modern Home * Wood-Stove Nights * Big Deck

Bright Modern Home * Wood-Stove Nights * Big Deck
Callicoon
€547
includes taxes & fees
10 Nov - 11 Nov
Bright Modern Home * Wood-Stove Nights * Big Deck
A covered outdoor area with a wooden deck and a view of a green landscape.
A covered outdoor deck with a round table and four chairs, surrounded by white railings and trees.
A bathroom with a wooden vanity, a mirror, and a glass-enclosed shower.
A wooden staircase with a cushioned bench at the bottom.

3. Inn at Tyler Hill

Inn at Tyler Hill
Tyler Hill
€132
includes taxes & fees
2 Nov - 3 Nov
Inn at Tyler Hill
An indoor venue with wooden beams, tables set for dining, and hanging greenery.
A wooden bridge leading to a building with a blue roof, surrounded by dense greenery.
A modern cabin with a wooden deck, large windows, and a black roof, surrounded by dense forest.
A triangular tent-style room with a bed, a small table, and a red lamp.

4. Callicoon Hills

Callicoon Hills
Callicoon Center
€288
includes taxes & fees
15 Oct - 16 Oct
Callicoon Hills
A rustic cabin with a stone foundation, surrounded by a well-maintained lawn and a variety of trees.
A rustic interior with stone walls, wooden beams, and large windows offering a view of the outdoors.
A rustic wooden interior with leather sofas, a round wooden coffee table, and a large window offering a view of a field.
A wooden interior with a ping pong table, tables, chairs, and large windows.

5. Roscoe Mountain Club

Roscoe Mountain Club
Roscoe
€117
includes taxes & fees
13 Oct - 14 Oct
Roscoe Mountain Club
A covered porch with outdoor seating, surrounded by lush greenery and a stone pathway.
A bar area with wooden cabinets, a counter with various bottles, and green chairs.
A bedroom with a large bed, a chair, a bedside table, and a wall-mounted lamp.
A cozy room with a wood-burning stove, a rocking chair, and a fireplace.

6. The North Branch Inn

The North Branch Inn
North Branch
€360
includes taxes & fees
25 Oct - 26 Oct
The North Branch Inn
A house with a covered porch and a grassy yard.
A bathroom with a bathtub, toilet, vanity with a mirror, and a window.
A house surrounded by trees and a river.
A pool table in a room with wooden flooring, a ceiling fan, and a billiards rack.

7. Callicoon Creek Farmhouse

Callicoon Creek Farmhouse
Callicoon
€377
includes taxes & fees
10 Nov - 11 Nov
Callicoon Creek Farmhouse
A modern lobby with a curved sofa, a reception desk, and a flat-screen TV.
A hotel room with two beds, a desk, a chair, and a large painting on the wall.
Accessible bathroom
A banquet hall with round tables covered in white tablecloths and chairs, a carpeted floor, and a ceiling with recessed lighting.

8. Days Inn by Wyndham Liberty/Monticello

Days Inn by Wyndham Liberty/Monticello
Liberty
  • Kids will love the arcade and pool fun at this family-friendly hotel with free activities and skiing nearby.
€94
includes taxes & fees
1 Nov - 2 Nov
Days Inn by Wyndham Liberty/Monticello
A modern living room with two sofas, a glass coffee table, and a painting of a horse.
A modern bathroom with a glass shower enclosure, a toilet, and a towel rack with folded towels.
A reception area with a marble counter, a wall-mounted artwork, and a ceiling with recessed lighting.
A large indoor swimming pool with a wooden deck and lounge chairs.

9. Best Western Monticello

Best Western Monticello
Monticello
  • Family retreat offers indoor pool, arcade, and sauna for year-round enjoyment near waterpark.
€115
includes taxes & fees
18 Oct - 19 Oct
Best Western Monticello
A modern kitchen area with a central island, various appliances, and a chalkboard wall with food-related drawings.
A hotel room with two beds, a nightstand with a lamp, a window with a view, and a carpeted floor.
An indoor swimming pool with clear signage, including "NO LIFEGUARD ON DUTY" and "NO DIVING" warnings.
A gym with treadmills, elliptical machines, and weightlifting equipment.

10. Hampton Inn Monticello

Hampton Inn Monticello
Monticello
€123
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn Monticello
View all properties

Choose what matters most at family-friendly hotels in Callicoon

Breakfast included
Pool
All-inclusive
4 stars
5 stars

Top Callicoon Hotel Reviews

The Hotel Belvidere

The Hotel Belvidere

8/10 Good
"Very Quiet"
Jeanne 3-night trip
Posted 4 days ago
The Hotel Belvidere
Days Inn by Wyndham Liberty/Monticello

Days Inn by Wyndham Liberty/Monticello

10/10 Excellent
"Restaurant was amazing . Staff very informative about history of Woodstock"
Mary 1-night trip
Posted 8 days ago
Days Inn by Wyndham Liberty/Monticello

Frequently asked questions

What's Callicoon like for family-friendly holidays?
The historic destination of Callicoon is a great choice if you've been considering a holiday with the children. The entertainment, excursions and recreation options are just some of the things that make this a good destination for family holidays.
What's the best family accommodation in Callicoon?
Villa Roma Resort and Conference Center is a resort with a children's pool and a children's club, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly holiday in Callicoon?
The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Callicoon are January, February, December and March, with each month seeing an average of 24 cm of snowfall.
What's there to see and do with your family in Callicoon?
While you and your family are holidaying in Callicoon, you may want to visit some family-friendly attractions such as The Museum at Bethel Woods and Carousel Water and Fun Park. Make sure that you have lots of time for activities such as Western Sullivan Public Library Tusten-Cochecton Branch and Tusten Theatre.