Top Vacation Homes in Montgomery County in 2026

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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 vacation homes

A wooden deck with a hot tub, surrounded by trees and string lights.

1. Treetop Designer Cabin · Hot Tub · Red River Gorge

Rogers

Gina M.

AED 1,113 total

includes taxes & fees

16 Nov - 17 Nov

A cabin with a deck, surrounded by trees with autumn leaves.

2. Retro Treetop Cabin | Hot Tub| Red River Gorge

Rogers

Ann O.

AED 1,113 total

includes taxes & fees

15 Nov - 16 Nov

A hot tub with a wooden deck and a cabin with a sign that reads 'Welcome to High Rock.'

3. Backyard Cliffs! RRG Cabin - Onsite Hike

Stanton

Kala M.

A cozy attic bedroom with a sloped ceiling, a bed with yellow pillows, a small chair, a dresser, and a window with a view of the outdoors.

4. Cozy Tiny Home Retreat - Near RRG Hiking + Hot Tub

Stanton

Kristian S.

A modern kitchen with white cabinets, stainless steel appliances, and a central island.

5. 50 Shades of Slade | Private Hot Tub, Pet-Friendly + 5 Minutes to Natural Bridge

Stanton

Jamie T.

A cozy seating area with a large window, a cushioned bench, and a small table with a lantern.

6. Good Vibes Only: Red River Gorge! Large Game Room! Hot Tub!

Clay City

Joshua L.

An outdoor deck with wicker furniture, a fire pit, and a view of a forested area.

7. Sandstone Lodge, Ride to Hollerwood + DBBB Access

Stanton

Jodi V.

A tent in a forest, a fire pit with chairs, and a bench.

8. Red River Gorge Cozy Glamping Tent for 4 • AC, Fire Pit & Hot Tub

Stanton

Kimberly J.

AED 847 total

includes taxes & fees

9 Nov - 10 Nov

A log cabin interior with a TV, sofa, and kitchen area.

9. Overlook Oasis! RRG, A-frame Cabin, NEW HOT TUB, Grill! Pet friendly

Campton,

Harrison

AED 1,049 total

includes taxes & fees

8 Nov - 9 Nov

A patio area with a fire pit, picnic table, and chairs, surrounded by trees and a building.

10. Sunny Days at the Gorge Your Red River Gorge Adventure & Wedding Venue Basecamp

Rogers

Veronica M.

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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.

A hotel room with a bed, a desk with a chair, a sofa, and a TV.

Comfort Inn & Suites Mount Sterling

Mount Sterling

10/10 Excellent

Gilda

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

Ramada Limited Mount Sterling

Mount Sterling

10/10 Excellent

Bonnie

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

Holiday Inn Express Lexington East - Winchester by IHG

Winchester

10/10 Excellent

Dennis

A hotel room with a large bed, a television, a desk with a chair, a wardrobe, and a window with curtains.

Hampton Inn Winchester

Winchester

10/10 Excellent

JDK

A hotel room with a bed, a sofa, a desk, and a wardrobe.

Holiday Inn Express and Suites Morehead by IHG

Morehead

10/10 Excellent

Brian

A log cabin interior with a stone fireplace, wooden walls, and a ceiling fan.

Natural Bridge State Resort Park

Slade

10/10 Excellent

Edgar

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

Best Western Winchester Hotel

Winchester

10/10 Excellent

Kimbery

A lodge with a sign reading "WORTHINGTON LODGE," surrounded by landscaped gardens and trees.

Blue Licks Battlefield State Resort Park

Carlisle

10/10 Excellent

Richard

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

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

A hotel room with a bed, a desk, a chair, a desk lamp, a window with curtains, an air conditioner, and a view of the outside.

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