Vacation rentals in Clark County

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Top-rated vacation rentals in Clark County

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Top guest favorite

A grassy path of stepping stones leads from a stone area to the entrance of the apartment, surrounded by well-maintained landscapes and shrubs. The gentle slope of the yard offers a view of the surrounding farmland under a cloudy sky.

Farm stay in Winchester

4.92 out of 5 average rating, 146 reviews

LenMar Farm Country Stay near Lexington KY

Farm stay in the heart of the Kentucky Bluegrass 20 min from the Kentucky Horse Park and downtown Lexington. 30 min to Keeneland. 45 min to Red River Gorge. Quiet, private walk out basement apt. with 2 bedrooms, great room, and butlers pantry with coffeemaker, small refrigerator, microwave, and kitchen basics. Space is not shared. Eat indoors or out, fire pit and horses/cattle out back. Up to 2 well-behaved dogs with pre-approval from hosts. Dogs can’t be left alone. 2 night min, 10 night max.

Guest favorite

A spacious hallway features rich hardwood flooring and an arched entryway with exposed brick walls. Potted plants add a touch of greenery, while light fixtures provide illumination. A glimpse of a kitchen area and a bathroom can be seen in the background.

Loft in Winchester

5 out of 5 average rating, 36 reviews

Artist’s Loft 2Bdr Winchester, near Lexington KY

This stylish place is perfect for your visit to Central Kentucky. Located on I-64, it is a half an hour to the Horse Park, downtown Lexington, and red river gorge. This is also above an Italian restaurant, so you can easily get good eats for your stay but beware you do hear the hum of the exhaust fan. Both bedrooms have king size temperpedic mattresses. This 1890’s building has been lovingly restored to preserve many original features and character. We invite you in to support it’s renewed life!

Top guest favorite

A scenic view of the property is presented, showcasing vibrant autumn foliage against a bright blue sky. The grassy area is interspersed with colorful leaves, leading towards the welcoming home in the distance, surrounded by trees and a serene countryside setting.

Home in Winchester

4.98 out of 5 average rating, 56 reviews

Serene Country Refuge at The Right Angle * Remote

Discover peaceful country living, a secluded homestead retreat where modern comforts meet rustic charm. Tucked away on a narrow country road, this remote sanctuary offers a true escape. Wander our private trail, curl up with a book from our custom library, or gather around the crackling fire under a blanket of stars. Though wonderfully secluded, just 15 min from town, located between the adventures of RR Gorge and the culture of Lex, offering the perfect blend of isolation and accessibility.

Superhost

A sleek black reclining loveseat with built-in cup holders and a central tray is illuminated by soft blue lighting. The backdrop features a dining area with a small table and chairs, visible through large glass doors leading to the outdoor space.

Home in Winchester

4.81 out of 5 average rating, 27 reviews

The Winchester

Work groups or families welcome. Bring the whole family there is lots of room for everyone. Home covers all the bases from comfortable living spaces to movie watching or gaming in the theatre/game room. Many table games to choose from. Out door space with a 6 foot privacy fence. Fire pit , bbq grill, picnic table , deck, patio, covered front porch. Off street parking, Home is straight across the street from a nice city park. Close to lexington and Natural Bridge a huge tourist area.

Guest favorite

A charming exterior view of the house features a welcoming porch with decorative plants and an American flag. A concrete pathway leads from the sidewalk to the entrance, flanked by manicured lawn areas and mature trees providing shade.

Guesthouse in Winchester

4.94 out of 5 average rating, 194 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.

Guest favorite

A warm welcome is extended with a stylish doormat featuring the word 'hello' in a playful font. The mat sits at the base of a staircase leading to a darkly stained wooden staircase, complemented by a light wood floor.

Loft in Winchester

5 out of 5 average rating, 15 reviews

Hanna’s 1,400 SQ FT Downtown Royal Retreat Loft

1400 SQ.Ft in DT Winchester, KY. 1 bedroom 2 queen beds with 1.5 bathroom and laundry amenities . - experience luxurious living at an affordable price!!! -across the street from historical Courthouse -with Molder and Brand new furnishings and amenities to make this special aboard feel like home -Two Queen beds -two big TVs -Two new custom reclining couches, good for additional sleeping space -Private entrance+ample parking in the rear. Have fun at this unique and stylish place

Guest favorite

The front entrance of the cottage features a wooden door framed by two windows. A decorative wreath is hung on the door. A small red table and chairs are positioned on a brick path, welcoming visitors.

Home in Winchester

4.91 out of 5 average rating, 788 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 row of historic buildings along a city street features varied architecture and colorful facades. The structures include shops and offices, with large windows and decorative elements. Several parked cars are visible along the curb, and the clear blue sky provides a bright backdrop.

Apartment in Winchester

4.94 out of 5 average rating, 89 reviews

The Carriage Inn - 1-bdrm apt in historic downtown

Centrally located in historic downtown Winchester with views of the county courthouse. Apartment is upstairs in a building that was originally used as a carriage repair shop. It is within walking distance to lots of unique shops and restaurants and the Bluegrass Heritage Museum. Walk or drive to the Farmers Market (seasonal) on historic Depot Street on Saturday mornings. The Red River Gorge/Natural Bridge area is 40 minutes east. Lexington is a short 20-30 minutes west.

Superhost

A modern bathroom features a spacious jetted tub surrounded by elegant tile work. Shelves with decorative items are mounted on the wall, while a separate shower stall is visible in the corner. Soft light enters through a window, enhancing the relaxed atmosphere.

Farm stay in Winchester

4.82 out of 5 average rating, 103 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.

Top guest favorite

Farm stay in Winchester

4.97 out of 5 average rating, 115 reviews

Family Farm Winchester/Lexington 20 min.*Game Room

Franklin Ridge Farm is 5 minutes to DT Winchester close to Lexington Quick access to I64 close to I75 ***Discounts this coming Weekend Centrally located: Eateries & Historical Sites Lexington 20min State Parks Meadow Green Music Park 20min Keeneland 30.4mi. Kentucky Horse Park 30min Red River Gorge 35min Ark Encounter 45min Creation Museum 1hr 30min ~Home is surrounded by our family farm EST. 1803 at the beginning of Scenic Rt.15 So much to see & do

Guest favorite

A charming cabin exterior is surrounded by vibrant flowers blooming in a lush garden. Stone steps lead up through greenery to the front door, accentuated by window boxes with colorful plants. The cabin's rustic log section features a contrast with the lighter siding of the main structure.

Cabin in Lexington

4.82 out of 5 average rating, 563 reviews

Unique Stay - 1907 Log Cabin Near Kentucky River

Kirkland Cabin - Stay in a 1907 Log Cabin Perched on the Palisades of The Kentucky River in Lexington. * 2022 Updated Kitchen * King Bedroom and fun loft offering 2 single beds (ladder access) & 1 full bath. This is a cabin built in 1907 & has the character to prove it. Unplug with games or utilize High-speed WiFi. This cabin is 1 mile from I-75 & 15 minutes to downtown Lexington. Enjoy dinner < 1 mile away at Proud Marys BBQ w/ Live music (seasonal)

Top guest favorite

A charming outdoor area features a simple tent structure and a rustic wooden shed under the shade of lush green foliage. A natural stone path winds through the space, leading to the tent, while grassy patches and scattered rocks enhance the serene environment.

Tiny home in Richmond

4.97 out of 5 average rating, 109 reviews

The Stepping Stone Ranch

Cozy little mobile home located on a very beautiful horse farm (we welcome you to book a trail ride while you stay, just write in advance so we can get it booked as we do sometimes fill up)! Terrific location, only 15 minutes from Lexington, with many other outdoor activities in the area as well (ziplining, kayaking, Fort Booneborough). Also very close to multiple awesome restaurants with fun atmospheres (Proud Mary, Boonedogs, Halls on the River, etc.)