Top Chalets in Montgomery County in 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.

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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.

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

Stanton

Kelli O.

AED 833 total

includes taxes & fees

8 Nov - 9 Nov

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

2. Hot Tub Arcade Wifi Whispering Winds - Rrg!

Campton

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

3. Wifi - Pet Friendly - Secluded Knotty By Nature

Campton

A stone house with a balcony, surrounded by trees.

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

Rogers

Crystal J.

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

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

Rogers

Elizabeth I.

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

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

Stanton

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

7. Alone At Last

Campton

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

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

Rogers

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

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

Rogers

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

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

Stanton

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Top reviews in Montgomery County

A Holiday Inn Express & Suites building with a modern design, featuring a covered entrance and stone pillars.

Holiday Inn Express & Suites Mt Sterling North by IHG

Mount Sterling

10/10 Excellent

JimS.

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

Comfort Inn & Suites Mount Sterling

Mount Sterling

10/10 Excellent

Gilda

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

Ramada Limited Mount Sterling

Mount Sterling

10/10 Excellent

Bonnie

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.

Holiday Inn Express Lexington East - Winchester by IHG

Winchester

10/10 Excellent

Dennis

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

Hampton Inn Winchester

Winchester

10/10 Excellent

JDK

A Holiday Inn Express hotel with a prominent sign, multiple parking spaces, and a well-maintained lawn.

Holiday Inn Express and Suites Morehead by IHG

Morehead

10/10 Excellent

Brian

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

Natural Bridge State Resort Park

Slade

10/10 Excellent

Edgar

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

Best Western Winchester Hotel

Winchester

10/10 Excellent

Kimbery

A covered outdoor deck with a table and chairs, overlooking a forested area.

Blue Licks Battlefield State Resort Park

Carlisle

10/10 Excellent

Richard

A hot tub with a wooden deck and a wooden fence.

Plum Crazy: Hot Tub Cabin in Frenchburg

Frenchburg

10/10 Excellent

Plum crazy was BEAUTIFUL! It was impeccably clean. It smelled good as soon as you walked in the door. The linens smelled freshly washed. Inside the drawers were clean (no food crumbs). And the decor inside the house was so cute. From the chair hanging on the wall, the watering can shower head to the mouse house in the wall. Everything was spotless and beautiful. And the hot tub was located on a beautiful deck and it was well kept and so clean. The only criticism I have is that the yard needed...

Amy

Value Stay

Winchester

10/10 Excellent

This is a money saver motel. No frills, no bugs and no extras. The refrigerator, microwave and air conditioner and toilet were near new and functioning well. The carpet and sink are original from 1989 and in poor shape, the sink was draining very slowly but for the price of a clean room without bugs it wasn't an issue for us. The water saver shower head was annoying as could be but it's a hot shower and it was definitely clean so we lived with it. This isn't a vacation resort but if you're...

Crystal