Vacation rentals in Montgomery County

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Top-rated vacation rentals in Montgomery County

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Top guest favorite

A spacious bedroom is illuminated by natural light from triangular windows. A comfortable king-sized bed is featured, complemented by a warm-toned area rug beneath. A stylish brown couch is positioned near the window, and a clothing rack with hangers provides additional storage.

Apartment in Mount Sterling

4.96 out of 5 average rating, 77 reviews

Historic 2-Bedroom Apartment in Downtown

Charming apartment in the historic Farmers National Bank building in downtown Mount Sterling. Recently renovated, the apartment provides the comfort and amenities of home, yet retains all of the character of the original building. Within walking distance of many great restaurants and if you’re in the mood to shop, stop in to Lily Aesthetics downstairs or take a stroll down Main Street to find a variety of great shopping opportunities. Located within 35 miles of Lexington and the Red River Gorge.

Top 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, 18 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.

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, 4 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.

Cabin in Jeffersonville

5 out of 5 average rating, 3 reviews

Cozy Red River Gorge Cabin

New owner of loved cabin with BRAND NEW beds and mattresses! Escape with your family or friends to our secluded, pet friendly Red River Gorge home. Located 20 min from RRG and 45 min from Lexington, you'll wake up every morning to the relaxing sounds of nature. Start your day with coffee or a book on the peaceful screened in porch. Take a hike. Wind down in the evening with a game of cards or s’mores by the fire. Whatever your adventure, we hope you'll make lifetime memories in our cabin.

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, 48 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, 17 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.

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

4.83 out of 5 average rating, 216 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, 88 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, 81 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.

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, 26 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.

A cozy living area is featured, with a spacious grey sectional sofa adorned with decorative pillows. A heated massage chair sits nearby, complemented by a small table and a stylish area rug. Natural light enters through large windows, and a wall art piece adds a touch of elegance.

Home in Mount Sterling

4.73 out of 5 average rating, 49 reviews

Magnolia bluff

Forget your worries in this spacious and serene space. Enjoy a multi-functional therapeutic massage in the heated massage chair while watching the 55 inch smart tv. The zero gravity massage chair provides a full body relaxation from the neck down to the legs. Get a great workout without leaving the privacy of your home. Dedicated work out room with an elliptial machine, rowing machine, weights, push-up bars, yoga mat and more.