Chalets in Montgomery County
Kentucky
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A river winding through a densely forested valley with rocky cliffs on one side.

Chalets in Montgomery County

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your current months are November, 2026 and December, 2026.

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Top cities in Montgomery County

An aerial view of a town with historic buildings, a central green area, and a parking lot.

Mount Sterling

Jeffersonville

Camargo

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Our top choices for Montgomery County chalets

A wooden deck with benches, a railing, and a view of a forested area.

A cozy wooden cabin bedroom with a bed, a window with blinds, a bedside table with a lamp, and a chair.

A wooden cabin interior with a stone fireplace, wooden dining table, and chairs.

A wooden cabin interior with a kitchen featuring white cabinets, a refrigerator, and a dining table with chairs.

1. Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.

Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.

Stanton

9.4 out of 10, Exceptional, (29 reviews)

9.4/10

Exceptional

(29 reviews)

"We loved our stay! The cabin was peaceful, secluded, and the perfect place to relax. The hot tub and fire pit were our favorite parts, and we can't wait to come back."

Kelli O.

The price is CA $184

CA $184

CA $318 total

includes taxes & fees

Nov 8 - Nov 9

Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.

A cozy cabin interior with a wooden interior, a sofa, a television, and a kitchen area.

A wooden cabin interior with a dining area, a sofa, and a staircase leading to another level.

A cozy wooden cabin interior with a sofa, two patterned chairs, a small table, and a fireplace.

A wooden cabin with a hot tub on a wooden deck, surrounded by trees.

2. Hot Tub Arcade Wifi Whispering Winds - Rrg!

Hot Tub Arcade Wifi Whispering Winds - Rrg!

3.0 star property

Campton

Hot Tub Arcade Wifi Whispering Winds - Rrg!

A wooden deck with a railing, surrounded by tall trees and a clear blue sky.

A cozy living room with a wooden staircase, a flat-screen TV, a sofa, a loveseat, and a red chair.

A cozy cabin interior with wooden walls, a red sofa, a brown leather couch, and a Christmas tree.

A rustic cabin interior with a wooden dining table, chairs, a sofa, and a chandelier.

3. Wifi - Pet Friendly - Secluded Knotty By Nature

Wifi - Pet Friendly - Secluded Knotty By Nature

3.0 star property

Campton

Wifi - Pet Friendly - Secluded Knotty By Nature

A stone house with a balcony, surrounded by trees.

A wooden interior with a bathroom featuring a white sink, mirror, and towel rings.

A forest with a wooden staircase leading up.

Spacious kitchen with granite countertops and cozy stone fireplace with electric insert.

4. Updated Lake House, set atop the hill overlooking beautiful Deer Water Lake.

Updated Lake House, set atop the hill overlooking beautiful Deer Water Lake.

Rogers

8.4 out of 10, Very good, (38 reviews)

8.4/10

Very good

(38 reviews)

"We had a wonderful time and couldn't have asked for a better stay! Everything was perfect from start to finish. The location was excellent—close to all the attractions, making it easy to get everywhere we wanted to go. The accommodations were comfortable, and everything exceeded our expectations. We would definitely stay here again and highly recommend it to anyone visiting the area!"

Crystal J.

Updated Lake House, set atop the hill overlooking beautiful Deer Water Lake.

A cabin with a red roof, surrounded by dense forest and rocky terrain.

A cabin with a porch, outdoor seating, and a fire pit.

A wooden interior with a bar area, stools, and a sofa.

A spacious kitchen with wooden beams, a stone fireplace, and modern appliances.

5. Exquisite, luxurious, stunning view, private, authentic log cabin

Exquisite, luxurious, stunning view, private, authentic log cabin

Rogers

9.4 out of 10, Exceptional, (13 reviews)

9.4/10

Exceptional

(13 reviews)

"Beautiful location, secluded and plenty of space to relax. Great spot for us with our 2 teens. So close to lots of activities in the gorge too!"

Elizabeth I.

Exquisite, luxurious, stunning view, private, authentic log cabin

A spacious loft with a high ceiling, a wooden staircase, a leather sofa, and a kitchen area.

A wooden staircase with a railing leading to a room with large windows and a view of greenery outside.

A wooden deck with a green metal roof, a dining area with outdoor furniture, and a view of a forested area.

A kitchen with a wooden ceiling, a central island with bar stools, and a refrigerator.

6. Hot Tub - Haven at the Red - Red River Gorge, KY

Hot Tub - Haven at the Red - Red River Gorge, KY

3.0 star property

Stanton

Hot Tub - Haven at the Red - Red River Gorge, KY

A hot tub in a wooden cabin with a view of the surrounding forest.

A modern kitchen with stainless steel appliances, a dining area with a wooden table and chairs, a living room with a sofa and fireplace, and a TV mounted on the wall.

A bedroom with a bed, two bedside tables with lamps, a ceiling fan, and a sliding glass door leading to an outdoor area.

A kitchen with wooden shelves, a sink, and a window.

7. Alone At Last

Alone At Last

3.0 star property

Campton

Alone At Last

A log cabin interior with a staircase, a living room with a sofa, a water dispenser, and a window with curtains.

A wooden cabin bedroom with a bed, a nightstand, a window with curtains, and a wall-mounted lamp.

A cozy wooden cabin bedroom with a bed, a TV, and a view of the outdoors.

A cozy room with a wooden cabinet containing board games like Battleship and UNO. There's a table with chairs, a window with curtains, and a view of greenery outside.

8. Hot Tub & Wifi - Hillside Haven Red River Gorge KY

Hot Tub & Wifi - Hillside Haven Red River Gorge KY

3.0 star property

Rogers

Hot Tub & Wifi - Hillside Haven Red River Gorge KY

A cozy log cabin interior with a fireplace, leather sofa, and a staircase.

A modern kitchen with stainless steel appliances, wooden cabinets, and a dining area with a wooden table and chairs.

A spacious cabin with a loft bedroom, a cozy living area with a leather sofa, and a stone fireplace.

A spacious cabin interior with a kitchen, dining area, and a staircase leading to a loft bedroom.

9. Wifi, Hot Tub & Pets - Eaglerock Retreat in Rrg!

Wifi, Hot Tub & Pets - Eaglerock Retreat in Rrg!

3.0 star property

Rogers

Wifi, Hot Tub & Pets - Eaglerock Retreat in Rrg!

A hot tub on a wooden deck with a view of a forest.

A wooden interior with a kitchen featuring a double door, a microwave, a stove, and a refrigerator.

A cozy living room with a leather armchair, a grey sofa with patterned cushions, and a coffee table. A staircase with wooden railings leads to a kitchen area.

A compact kitchen with wooden cabinets, a stainless steel refrigerator, a washing machine, and a clock on the wall.

10. Hot Tub, Wifi & Pet-friendly - Pilot Point

Hot Tub, Wifi & Pet-friendly - Pilot Point

3.0 star property

Stanton

Hot Tub, Wifi & Pet-friendly - Pilot Point

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top reviews in Montgomery County

An indoor swimming pool with clear water, a pool ladder, and lounge chairs.

A hotel lobby with a blue sofa, armchair, and a coffee station.

A Comfort Inn & Suites building with a yellow facade, brick accents, and a clear blue sky.

A hotel lobby with a blue sofa, armchairs, a coffee table, and a reception desk.

Comfort Inn & Suites Mount Sterling

Mount Sterling

10/10 Excellent

Nice clean hotel. Falsely advertised as pet friendly though; hotel is not pet friendly. Only service dogs are allowed.

Dolina

Reviewed December 21, 2023Reviewed December 21, 2023

Comfort Inn & Suites Mount Sterling

A lobby with two armchairs, a fireplace, and a large mirror.

A building with a brick facade, surrounded by well-maintained landscaping including various shrubs and flowering plants.

A gym with treadmills, a weight machine, and mirrors on the walls.

A breakfast buffet with various food items and a pitcher of milk.

Ramada Limited Mount Sterling

Mount Sterling

10/10 Excellent

Great property

Nasim

Reviewed June 30, 2024Reviewed June 30, 2024

Ramada Limited Mount Sterling

A hotel room with a large bed, a desk with a chair, a window with a view of the outside, and a wall-mounted TV.

A reception area with two illuminated reception desks, a wall-mounted sign, and a Coca-Cola refrigerator.

A buffet area with multiple food service stations, including omelets and other prepared dishes.

A Holiday Inn Express building with a covered entrance, stone pillars, and potted plants.

Holiday Inn Express Lexington East - Winchester by IHG

Winchester

8/10 Good

Good place to stay

martin

Reviewed April 30, 2025Reviewed April 30, 2025

Holiday Inn Express Lexington East - Winchester by IHG

A Hampton Inn hotel with a large parking lot, a prominent sign, and a clear sky.

A reception desk with a 'Manager On Duty' sign, framed pictures on the wall, and a 'Welcome to Winchester' sign.

A hotel breakfast area with a checkered floor, wooden cabinets, a microwave, and various breakfast items.

A store interior with shelves stocked with snacks and treats, a chalkboard sign reading 'Local Flavor,' and a 'Treats' sign on the wall.

Hampton Inn Winchester

Winchester

10/10 Excellent

Beds were better than expected

Ryan

Reviewed May 15, 2025Reviewed May 15, 2025

Hampton Inn Winchester

A wooden deck with a railing, a person sitting on a chair, and another person standing and looking through binoculars.

A spacious dining area with wooden tables and chairs, large windows offering a view of the outdoors, and a high ceiling with chandeliers.

A log cabin interior with a wooden floor, a sofa, a chair, a dining table, and a stone fireplace.

A swimming pool with a lifeguard stand, a no diving sign, and a covered area with lounge chairs.

Natural Bridge State Resort Park

Slade

10/10 Excellent

We were so impressed with the whole experience

Tammy

Reviewed July 29, 2025Reviewed July 29, 2025

Natural Bridge State Resort Park

A hotel with a modern design, featuring a large building with multiple balconies and a well-maintained lawn.

A restaurant with a counter, tables, chairs, and a kitchen area with appliances and food items.

A lobby with two armchairs, a reception desk, and a chandelier.

A hotel room with a bed, two bedside tables, a desk, a chair, and a lamp.

Best Western Winchester Hotel

Winchester

10/10 Excellent

Fix the cold water dispenser

Paul

Reviewed May 17, 2025Reviewed May 17, 2025

Best Western Winchester Hotel

A scenic overlook with a stone retaining wall, wooden railing, and a cable car system in the background.

A log cabin with a covered porch and several wooden chairs.

A wooden signboard for Black Bear Lodge with a contact number.

A two-story log cabin with a balcony, a covered porch, and a gravel driveway.

Black Bear Lodge Motel

Slade

10/10 Excellent

Love it, would totally rent there again

phil

Reviewed October 19, 2024Reviewed October 19, 2024

Black Bear Lodge Motel

A Baymont Inn & Suites building with a 'Newly Renovated' sign, featuring a modern design with large windows and a prominent corner tower.

A swimming pool with wooden walls and large windows offering views of greenery.

A Baymont Inn & Suites reception area with a blue accent wall, a large window with a view of a pool, and a modern reception desk.

A hotel room with two beds, a sofa, a desk, and a window with blinds.

Baymont by Wyndham Winchester

Winchester

10/10 Excellent

Très bien

Alexandra

Reviewed August 9, 2026Reviewed August 9, 2026

Baymont by Wyndham Winchester

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Chalets in Montgomery County

Change your mind

Treat yourself

Be picky

Top cities in Montgomery County

Mount Sterling

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Montgomery County chalets

1. Secluded 2-BD cabin, tranquil mountain setting. Hot Tub Gazebo! Wood fireplace.

2. Hot Tub Arcade Wifi Whispering Winds - Rrg!

3. Wifi - Pet Friendly - Secluded Knotty By Nature

4. Updated Lake House, set atop the hill overlooking beautiful Deer Water Lake.

5. Exquisite, luxurious, stunning view, private, authentic log cabin

6. Hot Tub - Haven at the Red - Red River Gorge, KY

7. Alone At Last

8. Hot Tub & Wifi - Hillside Haven Red River Gorge KY

9. Wifi, Hot Tub & Pets - Eaglerock Retreat in Rrg!

10. Hot Tub, Wifi & Pet-friendly - Pilot Point

Top reviews in Montgomery County

Comfort Inn & Suites Mount Sterling

10/10 Excellent

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