Condo Rentals in Montgomery County
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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 condo rentals

A modern kitchen with grey cabinets, stainless steel appliances, and a brick accent wall.

A modern kitchen with a large island, stainless steel appliances, and a unique chandelier.

A spacious living area with a leather chair, a white sofa with patterned cushions, and a pink tray table.

A staircase with a brick wall on one side and a black planter wall with various plants and flowers.

1. Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge

Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge

Winchester

10.0 out of 10, Exceptional, (11 reviews)

10/10

Exceptional

(11 reviews)

"It was a great experience, get communication and loved the space!"

Amanda F.

Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge

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

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

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

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

A hotel room with a bed, a bathroom, and a large mirror.

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

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

An indoor swimming pool with a lifeguard chair, a pool ladder, and a sign indicating no diving allowed.

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

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

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.

Hampton Inn Winchester

Winchester

10/10 Excellent

Beds were better than expected

Ryan

Reviewed May 15, 2025Reviewed May 15, 2025

Hampton Inn Winchester

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

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

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

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

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

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

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.

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

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

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

A wooden cabin room with a bed, a nightstand, and a painting on the wall.

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

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

A hotel dining area with a coffee station, a clock, and large windows offering a view of the outside.

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.

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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Flights from Vancouver (YVR) to Lexington (LEX)
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Search Condos Rentals in Montgomery County from CA $75

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 condo rentals

1. Large Downtown Artist's Loft, 30 min to Lexington, Horse, Bourbon, R River Gorge

Top reviews in Montgomery County

Comfort Inn & Suites Mount Sterling

10/10 Excellent

Explore a world of travel with Expedia