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

Find Family Hotels in Callicoon, NY from CA $143

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Check availability on Callicoon Family Hotels

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 fountain with water jets in the center, surrounded by a circular stone border. In the background, there is a building with a balcony and arched windows.
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.
CA $224
CA $282 total
includes taxes & fees
Oct 8 - Oct 9
Villa Roma Resort and Conference Center
A wooden deck with Adirondack chairs and a small table, overlooking a garden.
A spacious living area with a large sofa, a dining table with chairs, and a view of a deck with a wooden railing.
A modern kitchen with a central island, stainless steel appliances, and wooden shelves.
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
CA $197
CA $817 total
includes taxes & fees
Nov 2 - Nov 3
Bright Modern Home * Wood-Stove Nights * Big Deck
A covered porch with outdoor seating, surrounded by lush greenery and a stone pathway.
A cozy room with a wood-burning stove, a rocking chair, and a fireplace.
A garden with a gazebo, various flowering plants, and a pathway.
A bar area with wooden cabinets, a counter with various bottles, and green chairs.

3. The North Branch Inn

The North Branch Inn
North Branch
CA $434
CA $573 total
includes taxes & fees
Oct 25 - Oct 26
The North Branch Inn
A covered outdoor area with a wooden deck and a view of a green landscape.
A wooden staircase with a cushioned bench at the bottom.
A neatly made bed with white linens, a wooden headboard, and two bedside lamps. A window with curtains is visible, and a small table with a chair is in the corner.
A covered outdoor deck with a round table and four chairs, surrounded by white railings and trees.

4. Inn at Tyler Hill

Inn at Tyler Hill
Tyler Hill
CA $178
CA $194 total
includes taxes & fees
Nov 2 - Nov 3
Inn at Tyler Hill
An indoor venue with wooden beams, tables set for dining, and hanging greenery.
A modern cabin with a wooden deck, large windows, and a black roof, surrounded by dense forest.
A wooden bridge leading to a building with a blue roof, surrounded by dense greenery.
A large house with multiple sections, including a patio area with outdoor furniture and a stone pathway.

5. Callicoon Hills

Callicoon Hills
Callicoon Center
CA $198
CA $419 total
includes taxes & fees
Oct 8 - Oct 9
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 lodge with a green roof, surrounded by tall pine trees and a well-maintained lawn.
A wooden interior with a ping pong table, tables, chairs, and large windows.

6. Roscoe Mountain Club

Roscoe Mountain Club
Roscoe
CA $127
CA $143 total
includes taxes & fees
Oct 20 - Oct 21
Roscoe Mountain Club
A motel with a covered porch, outdoor seating, and flower planters.
A hotel reception desk with a desktop computer, a window with a view of the outside, and various informational brochures.
A hotel room with a flat-screen TV mounted on the wall, a wooden dresser with drawers, a tray with toiletries, and a sign on the wall.
A building with a covered porch, a door labeled "OFFICE," and a well-maintained lawn with a tree and potted plants.

7. Upper Delaware Inn

Upper Delaware Inn
Hancock
CA $173
CA $190 total
includes taxes & fees
Oct 11 - Oct 12
Upper Delaware Inn
A modern lobby with a curved sofa, a reception desk, and a flat-screen TV.
A banquet hall with round tables covered in white tablecloths and chairs, a carpeted floor, and a ceiling with recessed lighting.
A spacious indoor area with multiple tables and chairs, a kitchen area with a counter, and a large window providing natural light.
A hotel room with two beds, a desk, a chair, and a large painting on the wall.

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.
CA $124
CA $140 total
includes taxes & fees
Nov 1 - Nov 2
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.
CA $161
CA $182 total
includes taxes & fees
Oct 13 - Oct 14
Best Western Monticello
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.

10. Callicoon Creek Farmhouse

Callicoon Creek Farmhouse
Callicoon
CA $178
CA $496 total
includes taxes & fees
Oct 8 - Oct 9
Callicoon Creek Farmhouse
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 19 hours 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 4 days ago
Days Inn by Wyndham Liberty/Monticello
Lake Wanoka Resort

Lake Wanoka Resort

10/10 Excellent
"It’s magic place. I love that"
Zaira 1-night trip
Posted 7 days ago
Lake Wanoka Resort

Frequently asked questions

What's Callicoon like for family-friendly vacations?
The historic destination of Callicoon is a great choice if you've been considering a vacation with the kids. The entertainment, excursions, and recreation options are just some of the things that make this a good place for family vacations.
What's the best accommodation when traveling with kids to Callicoon?
Villa Roma Resort and Conference Center is a resort with a children's pool and a kids' club, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly vacation in Callicoon?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Callicoon are January, February, December, and March, with each month seeing an average of 9 inches of snowfall.
What's there to see and do with your family in Callicoon?
While you and your family are vacationing in Callicoon, you might want to visit some family-friendly attractions such as The Museum at Bethel Woods and Carousel Water and Fun Park. Make sure you have lots of time for activities like Western Sullivan Public Library Tusten-Cochecton Branch and Tusten Theatre.

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