Vacation rentals in Mount Sterling

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Top-rated vacation rentals in Mount Sterling

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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.

Guest favorite

An open living space features polished wood flooring and neutral walls. A circular coffee table sits at the center, surrounded by a cozy seating area. Bar stools line a kitchen counter, and glass doors lead to a deck, framed by checkered drapes for a rustic charm.

Apartment in Clay City

4.87 out of 5 average rating, 63 reviews

Gran's Guest House RRG! Back to School Specials!

Located less than 20 minutes from the Red River Gorge and less than 5 minutes from the Kentucky Dragway is “Gran’s Guest House,” which has a farmhouse style that is practical, simple, and rustic, yet also embraces modern comforts that create a look that feels both cozy and stylish. Also only minutes away from the hidden treasure of Pilot Knob, a hiking overlook a hiking overlook considered to be the prominence upon which Daniel Boone first looked out over the Bluegrass region of Kentucky.

Top guest favorite

A rustic cabin is nestled among vibrant autumn trees, positioned above a serene pond. A small dock with two chairs is visible near the water's edge, inviting relaxation. The surrounding landscape features lush greenery and colorful foliage, enhancing the cabin's secluded feel.

Cabin in McKee

4.97 out of 5 average rating, 392 reviews

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

Guest favorite

A traditional bedroom showcases a four-poster bed with a patterned comforter. A decorative lamp sits on a bedside table, and a vintage console table with a plant adds a touch of greenery. Natural light enters the room through the open door, enhancing the serene ambiance.

Guesthouse in Winchester

4.93 out of 5 average rating, 204 reviews

Carriage House on the Park

Enjoy the tranquility of this Upstairs Apartment (over 400 sq ft) suite, located across from Winchester's College Park. Executive amenities include heated bathroom floor tile, additional sink and vanity and large flat screen Roku Smart TV. Carriage house is located just steps from public gym and recreational center and historic downtown Winchester. Centrally located with easy access to Lexington, Paris, Versailles, Georgetown, Kentucky Horse Park, Natural Bridge and Red River Gorge.

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, 83 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

The entrance of the cottage features a wooden door framed by two windows, offering natural light. A decorative wreath adorns the door, and wall sconces provide additional illumination. The exterior showcases white siding with teal accents, complemented by a brick pathway leading to the door.

Home in Winchester

4.91 out of 5 average rating, 832 reviews

Cozy Cottage

Sweet little cottage within walking distance of historic downtown Winchester. Open floor plan, 500 square feet of coziness! Queen size bed, kitchen, living room, dining all in one place. We’re a working farm on the edge of the city limits in an older non-gentrified neighborhood. Surrounded by the Kentucky Horse Park, Keeneland, Rupp Arena, Fort Boonesboro, Red River Gorge and the Kentucky Bourbon Trail. Easy access to I-64, I-75, and Mountain Parkway - gateway to Appalachia.

Top guest favorite

A charming cabin is illuminated at night beside a stocked fishing pond. Water gently cascades from a fountain, creating a serene atmosphere. The surrounding landscape features trees and an open area, enhancing the sense of tranquility under the starry sky.

Tiny home in Stanton

4.99 out of 5 average rating, 145 reviews

Tiny Cabin At The Pond

Welcome to peace and quiet! If seclusion is what you're searching for, then you have found the place! Located on a hobby farm beside of a stocked fishing pond, it's as much of a destination as it is an accommodation. The closest neighbors are 3 friendly donkeys that love to greet guests at the fence for attention and ear rubs. Fishing poles and donkey treats are provided to round out your stay. We're 20 scenic minutes to Slade or Stanton and 25 to Mount Sterling.

Guest favorite

Farm stay in Winchester

4.81 out of 5 average rating, 129 reviews

The Winchester Retreat

Welcome to the Winchester Retreat! We are located right off of I-64 in Winchester, just 30 minutes from both Lexington and the Red River Gorge. We're right down the street from Winchester's downtown, boasting restaurants, breweries, and shops. Pet friendly!! Come spend an evening by the fire pit and whip up a great dinner using our fully equipped kitchen or charcoal grill. We're also close to Legacy Grove Park, complete with a walking trail and dog park.

Guest favorite

The living area features a spacious sectional sofa, a wooden coffee table, and a small dining area with two chairs. Light-colored walls and a ceiling fan contribute to the room's ambiance. A colorful artwork hangs above the sofa, and a white refrigerator is visible in the background.

Townhouse in Stanton

4.88 out of 5 average rating, 95 reviews

Red River Unit 4 - Firepit, central AC, Wi-Fi.

<b>20% OFF FOR A WEEK! 30% OFF FOR 28 DAY STAYS! STAY 30 DAYS OR MORE AND PAY NO TAXES! BEST VALUE FOR RED RIVER GORGE! CLIMBERS AND HIKERS WELCOME! 2 SEPERATE BEDROOMS </b> 12 miles to RRG, right next to Kroger. Easy access, no need for 4x4, its right in town! - Duplex right side - Central A/C and heat. - washer/dryer/gas stove - Fiber wifi - 4k Roku TV - Off street parking, private driveway fits 2 to 3 vehicles. PLEASE READ HOUSE RULES FOR PETS.

Guest favorite

A retro-inspired kitchen space features a round white dining table surrounded by four red chairs. Black and white checkered flooring complements the vintage decor, while a light-filled window dressed with playful curtains adds warmth. A classic phone and wall clock are visible on the gray walls.

Home in Stanton

4.93 out of 5 average rating, 99 reviews

Climbers Choice RRG Stay-Wifi-No cleaning fee

We'll have you feeling like a local in two days minimum and in a town so friendly you might just become one. Fully furnished duplex (SIDE A) minutes drive from the best Red River Gorge hiking trails, climbing, Miguel's, Natural Bridge State Park, The Gorge Underground, Callie's Lake, La Cabana & Kroger. Located in Stanton at beginning of Scenic Byway. Side A & B can be booked together if availability allows.

Top guest favorite

A comfortable living room is presented, featuring two plush armchairs and a spacious sectional sofa with cushions. A coffee table is positioned centrally, while a stone fireplace adds a rustic element. Large windows provide natural light, framing views of the surrounding nature.

Cottage in Clay City

4.98 out of 5 average rating, 121 reviews

Scenic views, farm fun in peaceful modern cottage

A family-friendly farm that offers opportunities for couples, families or small groups to create special memories. Our farm is also the perfect place for unique family adventures, family reunions, retreats, parties of any type and intimate weddings - all in an idyllic country setting (events charged separately). We offer educational tours and introductions to our animals for guests that are interested.

Guest favorite

A welcoming living space features hardwood flooring and soft gray walls. A comfortable sofa and patterned armchairs are arranged around a rustic coffee table. Ceiling fans provide ventilation, while large glass doors open to a view of the expansive yard.

Farm stay in Carlisle

4.99 out of 5 average rating, 161 reviews

Hilltop Retreat at Wendt’s Wildlife Adventure

Take it easy at this unique and tranquil getaway. Newly remodeled home on a 125 acre farm that is home to Kentucky’s newest wildlife park & Daniel Boone’s last home in Kentucky. Expansive views, and a visit to Wendt’s Wildlife Adventure (open seasonally), which is owned & operated by your hosts, are sure to give you just the right amount of rest & adventure that you are seeking.