Callicoon Holiday Rentals, New York: Private House Rentals

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

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Our top choices for Callicoon hotels

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 hotel reception area with a wooden reception desk, multiple computer monitors, and a large chandelier.

A grand staircase with ornate railings and a chandelier at the top.

A hotel lobby with round tables, cushioned chairs, a large pillar, and a projection screen displaying a movie.

1. Villa Roma Resort and Conference Center

Callicoon

DIANE

฿4,241

฿5,467 total

includes taxes & fees

26 Oct - 27 Oct

A covered outdoor area with a wooden deck and a view of a green landscape.

A cozy room with a wooden desk, a cushioned sofa, a flat-screen TV, and a window with curtains.

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 breakfast plate with scrambled eggs, bacon, and potatoes.

2. Inn at Tyler Hill

Tyler Hill

Roni

฿4,596

฿5,010 total

includes taxes & fees

2 Nov - 3 Nov

A covered porch with outdoor seating, surrounded by lush greenery and a stone pathway.

A garden with a gazebo, various flowering plants, and a pathway.

A cozy room with a wood-burning stove, a rocking chair, and a fireplace.

A bedroom with a large bed, a chair, a bedside table, and a wall-mounted lamp.

3. The North Branch Inn

North Branch

Georgia

฿10,301

฿13,607 total

includes taxes & fees

8 Nov - 9 Nov

A Hampton Inn hotel with a modern facade, a clear entrance, and a welcoming gas station.

A hotel room with two beds, a nightstand with a lamp, a window with a view, and a carpeted floor.

A modern kitchen area with a central island, various appliances, and a chalkboard wall with food-related drawings.

An indoor swimming pool with clear signage, including "NO LIFEGUARD ON DUTY" and "NO DIVING" warnings.

4. Hampton Inn Monticello

Monticello

ANN

฿4,133

฿4,670 total

includes taxes & fees

22 Nov - 23 Nov

A four-poster bed with a white bedspread, two bedside tables with lamps, a wooden door, and a framed picture on the wall.

A pathway flanked by trimmed trees leading to a building with a stone facade and multiple windows.

A two-story house with a stone facade and a large window.

5. Kenoza Lake View Manor

Jeffersonville

Norma

฿4,970

฿5,785 total

includes taxes & fees

1 Nov - 2 Nov

A triangular tent-style room with a bed, a small table, and a red lamp.

A wooden bridge leading to a building with a blue roof, surrounded by dense greenery.

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.

6. Callicoon Hills

Callicoon Center

Christopher

฿5,522

฿10,899 total

includes taxes & fees

29 Oct - 30 Oct

A modern living room with two sofas, a glass coffee table, and a painting of a horse.

A modern breakfast bar with a variety of food options, including a juice bar and coffee machines.

A large indoor swimming pool with a wooden deck and lounge chairs.

A hotel with a brick facade, a covered entrance, and a parking lot with cars.

7. Best Western Monticello

Monticello

Christine

฿3,833

฿4,331 total

includes taxes & fees

1 Nov - 2 Nov

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.

A spacious indoor area with multiple tables and chairs, a kitchen area with a counter, and a large window providing natural light.

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

Liberty

Eduardo

฿3,157

฿3,567 total

includes taxes & fees

1 Nov - 2 Nov

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 building with a covered porch, a door labeled "OFFICE," and a well-maintained lawn with a tree and potted plants.

9. Upper Delaware Inn

Hancock

Maura

฿4,102

฿4,513 total

includes taxes & fees

26 Oct - 27 Oct

A modern bar area with a central island, bar stools, and overhead lighting.

An indoor swimming pool with clear water, tiled floor, and a few lounge chairs.

An outdoor seating area with red chairs and tables, a fire pit, and a bar visible through the window.

10. Resorts World Catskills Casino

Monticello

Lagarian

฿6,047

฿7,677 total

includes taxes & fees

26 Oct - 27 Oct

A hotel with a pool area, outdoor seating, and a view of the sunset.

An indoor water park with a large water slide, a pool area, and a glass ceiling structure.

A bar area with a central island, multiple bar stools, and a large screen displaying content.

A restaurant setting with a counter, a digital scale, and a person serving food.

11. The Kartrite Resort & Indoor Waterpark

Monticello

Danely

฿4,367

฿7,342 total

includes taxes & fees

29 Oct - 30 Oct

A rustic cabin with a stone foundation, surrounded by a well-maintained lawn and a variety of trees.

A rustic wooden interior with leather sofas, a round wooden coffee table, and a large window offering a view of a field.

A rustic lodge with a green roof, surrounded by tall pine trees and a well-maintained lawn.

A rustic interior with stone walls, wooden beams, and large windows offering a view of the outdoors.

12. Roscoe Mountain Club

Roscoe

Donna

฿3,920

฿4,430 total

includes taxes & fees

28 Oct - 29 Oct

A two-story house with a front porch, a covered entryway, and a small garden area.

A modern kitchen with dark cabinetry, a stainless steel microwave, and an oven.

A spacious living room with a staircase, a dining area, and a decorative metal piece on the wall.

A bedroom with a bed, two bedside tables, a wall-mounted air conditioner, a framed picture, a door, and a patterned rug.

13. Windsong Retreat 2

Bethel

Joseph

฿9,420

฿11,980 total

includes taxes & fees

26 Oct - 27 Oct

A modern building with a wooden walkway leading to a covered entrance.

A restaurant with a long dining table, multiple chairs, and a high ceiling with hanging lights.

A modern living room with a stone fireplace, wicker furniture, and a flat-screen TV mounted on the wall.

A lakeside walkway with a wooden deck, surrounded by trees and a building with illuminated windows.

14. The Bradstan Boutique Hotel

Eldred

Alison

฿11,269

฿13,240 total

includes taxes & fees

2 Nov - 3 Nov

A sunroom with wooden beams, large windows, and a variety of potted plants.

A bedroom with a large bed, a nightstand with books, a lamp, and a view of a lake and trees through large windows.

A living room with a stone fireplace, two armchairs, a coffee table, and a bookshelf.

A large white house with a green roof, surrounded by a well-maintained lawn and a view of a lake.

15. Kenoza Hall

Kenoza Lake

Christopher

฿16,683

฿20,033 total

includes taxes & fees

1 Nov - 2 Nov

A traditional living room with a fireplace, a table with candles, a clock, and a chair.

A house with a green roof and a mailbox.

A two-story house with a green awning and a sign advertising a bed and breakfast.

A living room with two leather sofas, a glass coffee table, a lamp, and a floral rug.

16. Wayne on Main

Honesdale

Alex

฿4,558

฿4,968 total

includes taxes & fees

26 Oct - 27 Oct

A hotel with a red sign reading "ROOM" and a covered outdoor seating area with metal railings.

A bar area with a 'Hold 'em' sign, a refrigerator, and a variety of bottles.

A neatly made bed with a patterned throw, two bedside lamps, and a framed picture on the wall.

17. Hotel Wayne

Honesdale

Curtis

฿4,543

฿4,952 total

includes taxes & fees

26 Oct - 27 Oct

A rustic cabin-style hotel with outdoor seating and a fire feature.

A cozy living room with a fireplace, wooden furniture, and a variety of snacks and drinks on a table.

A cozy living room with a fireplace, comfortable seating, and a dining area.

A restaurant with a round table set for a meal, candles, and potted plants.

18. The Settlers Inn

Hawley

"Very nice hotel and our first visit there. The staff was very professional and friendly. Our room was very clean and had everything we needed. The breakfast in the hotel restaurant was excellent - wish we had more time to try dinner there. We were checking in at dinnertime and there was a line to get in. The outside grounds were so nice and there was a HUGE pumpkin to welcome us at the door. We will definitely go back again."

John

฿7,191

฿9,401 total

includes taxes & fees

24 Nov - 25 Nov

A modern lobby with a wooden accent wall, a seating area with sofas and ottomans, and a 'Museum Store' sign.

A large hotel with multiple buildings, a well-maintained lawn, and a lake nearby.

A person in a swimming pool with a tiled wall in the background.

A spacious indoor area with large windows and a high ceiling, suitable for group activities like yoga.

19. YO1 Longevity & Health Resorts, Catskills

Monticello

Suranie

฿11,775

฿13,306 total

includes taxes & fees

29 Oct - 30 Oct

A cozy indoor seating area with wooden beams, string lights, and potted plants.

A cozy log cabin interior with a fireplace, leather furniture, and large windows offering views of the outdoors.

A wooden building with a sign reading "The Arnold" and a garden with daffodils.

A cozy log cabin interior with a central seating area, wooden walls, and large windows.

20. The Arnold House

Livingston Manor

Leyla

฿11,821

฿14,539 total

includes taxes & fees

27 Oct - 28 Oct

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Stay near popular Callicoon attractions

Villa Roma Driving Range

This pristine driving range offers a serene Catskills backdrop for perfecting your swing technique. Practice various shots while enjoying the peaceful mountain scenery of Villa Roma Golf Club.

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Big Island

Commune with nature and explore the great outdoors at Big Island during your travels in Callicoon. Amble around the area's gardens or experience its entertainment choices.

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Villa Roma Go Kart Track

You can take time to visit Villa Roma Go Kart Track during your travels to Callicoon. Amble around the area's gardens or experience its entertainment choices.

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Learn more about Callicoon

This Delaware River town charms visitors with its historic Main Street shops and the restored Callicoon Theatre showing indie films. Kayak the gentle river currents or time your visit for the farmers' market where local musicians often perform on Sundays.

See all hotels in Callicoon

A lush green field with a hilly landscape in the background.

Top Callicoon Hotel Reviews

Days Inn by Wyndham Liberty/Monticello

10/10 Excellent

"Clean room"

Resorts World Catskills Casino

10/10 Excellent

"The hotel was great and so was the room besides some wear and tear in the furniture, the carpet was also dirty."

Wayne on Main

10/10 Excellent

"Excellent property. Great location. Clean room. Friendly stuff. Homey feel."

Best Western Monticello

8/10 Good

"Muy bonito lugar. Me encantó la pasé muy bien con mi esposa y mi hija. Un sitio para descansar de la rutina del trabajo. Muy recomendado de verdad"

Upper Delaware Inn

10/10 Excellent

"Great local hotel and the Pet-friendly room was clean and well kept. Plan to go back, would definitely recommend."

Inn at Tyler Hill

10/10 Excellent

"Awesome B&B, clean and great service."

Kenoza Lake View Manor

10/10 Excellent

"Beautiful place."

Super 8 by Wyndham Monticello NY

10/10 Excellent

"Great job with the redesign. Place looks awesome."

Hotel Wayne

10/10 Excellent

"Great for night or long stay. Has a lot of character"