Vacation rentals in Montgomery County

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Top-rated vacation rentals in Montgomery County

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Guest favorite

The spacious living area features a wooden interior with large windows allowing natural light. A comfortable dark leather sofa is arranged around a central coffee table. An entertainment area includes a TV and a circular mirror, while a door leads to one of the bedrooms.

Cabin in Jeffersonville

5 out of 5 average rating, 16 reviews

Endless View Cabin Rental

Endless View Cabin is conveniently located in the Red River Gorge/Natural Bridge area. It is a new construction (970 sq. feet of open floor plan). Bedroom 1 includes 1 queen size bed, dresser, hi-chest, nightstand and 55"TV. Bedroom 2 boosts a huge 4 adult queen size, Minnesota pine bunk bed with dresser. This cabin is dog friendly, loaded with board games for the family, has an outdoor fire pit, amazing views, quiet and secluded which allows for a great getaway for you and your friends/family.

Top guest favorite

The exterior of the luxury Barndominium is showcased at dusk, featuring a modern design with large windows. An expansive porch with seating is illuminated, highlighting the transition from outdoor to indoor spaces. A two-car garage is visible on the right side, set against a grassy area.

Home in Clay City

5 out of 5 average rating, 14 reviews

Modern Barndo|Hot Tub|Fire Pit|20 min RRG|Rec Room

Luxury Barndominium | Ultimate Game Room | 20 Mins to Red River Gorge This newly designed luxury Barndominium is packed with every amenity and game you can dream of, making it perfect for families, groups, and adventure seekers exploring the Red River Gorge, stargazing by the fire pit, lounging, or soaking in the hot tub. Games for all ages include pool, foosball, ping pong, darts, arcade games, multiplayer video game table, a dedicated small child play area, basketball, volleyball, and more!

A cozy living room features warm wooden walls and ceiling, complemented by soft lighting from stylish lamps. A comfortable sofa is positioned across from a television, with a round coffee table at the center. Nearby, a small dining table is set against a window, offering natural light.

Cabin in Mount Sterling

5 out of 5 average rating, 3 reviews

Rustic Mt. Sterling Cabin2 Near Downtown • Pets OK

Rustic Mt. Sterling Cabin 2 Near Downtown • Pets OK ★☆ ABOUT THIS SPACE ☆★ Tucked away in the rolling hills of Mt. Sterling, this rustic cabin offers the perfect blend of country charm and modern comfort. Just a short drive from the historic downtown district, you’ll have easy access to local shops, dining, and small-town charm—then come home to peace and quiet. Inside, unwind with a movie on the 55" smart TV, play a round of cards, or cook up something hearty in the fully equipped kitchen.

Superhost

A welcoming interior features a high, beamed ceiling with a chandelier above a large wooden table. Comfortable seating is arranged around a flat-screen TV, while sunlight filters through multiple windows. A red door adds a touch of color to the warm wood tones.

Cabin in Jeffersonville

4.81 out of 5 average rating, 47 reviews

Barn at Red River Gorge & Lexington

Location! Location! Location! Located only 15 minutes from Red River Gorge and Natural Bridge and 45 minutes from Lexington, this BRAND NEW 2 bedroom 1 bath barn cabin is the perfect place to relax and unwind. Relax and converse on the screened in back deck. Tell scary ghost stories around the fire pit. Cook those delicious hamburgers and hot dogs on the grill. Enjoy the amazing views of the Bluegrass and breathtaking stargazing from the overlook. Take a stroll throughout the woods.

Guest favorite

A charming two-story country home is set on a gently sloping lawn, featuring a red front door and several windows that allow natural light. Green shrubs and grass surround the entrance, complemented by a clear blue sky overhead.

Home in Sharpsburg

5 out of 5 average rating, 15 reviews

Firethorn’s Hilltop Haven

Country living at its finest. The home is nestled on a 140 acre seasonal working farm with lush open fields in scenic rural but Central Kentucky. This peaceful getaway gives a glimpse of what life on the farm and being in nature is like. Surrounded by open rolling fields, the perfect place to relax, take a walk, take a dip in the pool, or just be in nature. This home has it all. Family friendly. Pool available from May 19th to September 9th. Rates apply. Can park RV's & trailers.

Superhost

A cozy bedroom features blue walls adorned with butterfly decor and soft lighting. A queen bed is dressed with a floral comforter and surrounded by an inviting area rug. A small couch and side table add to the room's charm, with doors leading to additional living spaces.

Home in Mount Sterling

4.84 out of 5 average rating, 213 reviews

THE DOLLY - Cozy, Bright Home in Historic Downtown

Hello, Dolly! This bright and cozy home in the heart of downtown Mt. Sterling provides comfort and convenience. With hundreds of unique artifacts and rare photos to discover, you will find peace, relaxation, and tons of Dolly-themed photo ops! In addition to WiFi and Roku TV, guests will enjoy a massive collection of Dolly Parton films, records, and books. A fully-themed kitchen, bedroom, dining room, and bathroom offer many fun Dolly touches. A place so cute, even Jolene wants to stay!

Top guest favorite

The kitchen features a large central island with a dark finish, complemented by light granite countertops. Bright, white cabinetry surrounds the space, enhanced by overhead pendant lighting. Stainless steel appliances, including a refrigerator and microwave, provide modern convenience amid an open layout.

Home in Mount Sterling

5 out of 5 average rating, 86 reviews

High Street Hideaway home atmosphere for relaxing

High Street Hideaway, relax away from the city in a spacious well appointed home atmosphere. Large back deck for relaxing and dining. No need to park on the street and walk a flight of stairs! Private parking with 4-5 steps up to deck and back door! *Access to Lexington 30-45 minutes away via Interstate 64. * 45 minute drive to the natural beauty of Red River Gorge for hiking/ climbing *30 min to Cave Run Lake * Three blocks to local shops, eateries, and town festivals!

Top guest favorite

A cozy living area features a dark gray couch and two wooden chairs, complemented by a light area rug with a geometric pattern. A round mirror reflects light, and a floor lamp stands beside a window with horizontal blinds.

Loft in Mount Sterling

4.98 out of 5 average rating, 62 reviews

One Bedroom apartment with full kitchen

This a spacious and peaceful apartment located in historic Mt. Sterling, Kentucky just off of I-64. In 30 minutes you can be at Cave Run Lake, Red River Gorge or Lexington, Kentucky. It is also the perfect location for the popular 4 day “Court Days” which happens every third weekend in October! This apartment is 2 blocks walking distance to downtown Mt. Sterling, KY where you will find fun shopping and dining! This apartment is deep cleaned between bookings. Reserve today.

Guest favorite

The historic log cabin features a symmetrical facade with two front doors and multiple windows, framed by well-maintained greenery. A flag hangs proudly above one entrance, while a curved pathway leads guests to the inviting entry. The expansive lawn enhances the cabin's rustic charm.

Cabin in Winchester

4.91 out of 5 average rating, 79 reviews

Historic Cabin - Farm - Near RRG, Lex, local music

Join Laura, the founder of Laura's Lean Beef, Laura's Mercantile and Regeneration Distilling Co., at her farm at the edge of the bluegrass. The entire 1200 acres are open to guests, with easy access to the Red River Gorge, Winchester and Lexington. See farm animals and organic crops such as hemp, check out the aging barn for whiskey, while staying in an 18th century cabin updated with granite countertops, new beds and mattresses, modern bathrooms, and solar panels.

A modern interior is showcased with a wall-mounted television above a sleek, wall-inserted fireplace. Decorative shelves with potted plants create visual interest, while an air conditioning unit is positioned for comfort. Neutral-toned walls provide a calming backdrop.

Apartment in Mount Sterling

4.55 out of 5 average rating, 62 reviews

Montgomery Manor #11

Enjoy a stylish experience at this centrally located 1/2 mile from I-64 , only 40 miles from Cave Run Lake & Red River Gorge. A beautifully designed interior room with a queen size bed that sleeps two comfortably, 55 inch screen tv with a beautiful wall inserted fireplace. Gorgeous kitchenette with mini refrigerator lots of cabinet space, two burner stove top with plenty of counter space for cooking and a sink for dishes and a newly remodeled walk-in shower

Top guest favorite

A bright living area features a light-colored sofa with decorative cushions, complemented by two green armchairs. A round glass coffee table is positioned at the center, and large windows with charming designs allow natural light to fill the space. A decorative area rug adds warmth to the room.

Apartment in Mount Sterling

4.94 out of 5 average rating, 18 reviews

Charming Downtown Apartment

Introducing a charming two bedroom, one bathroom apartment nestled in the heart of downtown Mt. Sterling, Kentucky. This meticulously preserved gem invites you to step back in time while enjoying modern comforts. Located within the historic Farmers National Bank building, the space exudes character. Take a stroll down Main Street to find a variety of great restaurant and shopping opportunities. Located within 35 miles of Lexington and the Red River Gorge.

Top guest favorite

A modest bunkhouse is positioned on a sprawling green lawn, surrounded by gentle hills. A covered front porch invites relaxation, while a gravel driveway provides access. The landscape features a mix of trees and bushes, enhancing the rural charm of the setting.

Home in Jeffersonville

4.96 out of 5 average rating, 24 reviews

Welcome to the Bunkhouse!

The bunkhouse boasts 3 large bedrooms, two offer queen beds, while the master has a king. Two full baths and an additional sectional couch in the living room guarantee you plenty of room to spread out and enjoy your stay! Enjoy a peaceful stay on a working rare breed horse farm surrounded by large herds of both young and old horses as well as other farm animals. Gorgeous sunsets are as common as the gorgeous equines spotting the 70 acre farm.