Holiday rentals in Clark County

4.92 out of 5 average rating, 151 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.

4.98 out of 5 average rating, 63 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.

4.96 out of 5 average rating, 81 reviews

Loft in Winchester

Stylish Loft Historic Downtown 2Bdrm Winchester KY

New York style loft meets historic renovation—Central Kentucky. Meet charming Winchester. Under hr. to Keeneland race track, Kentucky Horse Park, & the spectacular Red River Gorge/Natural Bridge. Lexington 30 min. Paris, Georgetown, Richmond & Berea close too. Many local, small businesses-restaurants, brewery, distillery, shops, antiques, flea markets, & historical sites! Unit is on the second floor—may not be right for all abilities. Public, street parking. See our lovely town renovation.

Superhost

4.85 out of 5 average rating, 33 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.

4.98 out of 5 average rating, 62 reviews

River Duplex (private upstairs entrance)

An affordable and unique place to experience life on the river. River life may be peaceful but also can be rowdy, with several neighbor dogs, golf carts, welcoming to those that are open to an experience and can tolerate occasionally loud music and dog barking next door for a great price in a scenic location. **You will be sharing the house with a downstairs tentant **access to fire, laid back here! **NO Wifi and cat 🐈 and dog on property (No Team Mobile. Verizon, AT&T DO WORK!)

Guest house in Winchester

4.93 out of 5 average rating, 198 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.

4.91 out of 5 average rating, 808 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.

4.94 out of 5 average rating, 93 reviews

Flat in Winchester

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.

4.97 out of 5 average rating, 119 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 **Check-in & SAVE~June 16,17; 23,24,25,26,27 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

Superhost

4.81 out of 5 average rating, 112 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.

4.82 out of 5 average rating, 574 reviews

Cabin in Lexington

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)

4.97 out of 5 average rating, 114 reviews

Tiny home in Richmond

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.)

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Popular amenities for Clark County holiday rentals

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Other great holiday rentals in Clark County

Private room in Mount Sterling

4.77 out of 5 average rating, 22 reviews

The Savannah Retreat Heart of the Bluegrass

LaurenRating, 5 stars47 months ago

This house was beautiful! Everyone is so friendly! If you close the door to the bedroom it can get pretty cold in there! There’s also some pretty white cats that come around the house. Wet food was provided and I fed them everyday! The driveway is a bit rocky, but I drove my Nissan Sentra and it did fine!

Cabin in Mount Sterling

4.64 out of 5 average rating, 28 reviews

Peaceful Mt Sterling Cabin: Deck & Fire Pit!

MatthewRating, 5 stars6 months ago

The cabin offers spacious accommodations. The area is scenic and peaceful. Feels like you’re deep in the woods and off the beaten path, while only 10 minutes from all amenities and accommodations.

Superhost

4.81 out of 5 average rating, 21 reviews

The Winchester 2

MirbekRating, 5 stars1 month ago

A wonderful vacation home! Everything was clean, cozy, and thoughtfully arranged. We especially enjoyed the billiards table — great fun for evening entertainment. A special thank you to the host — very friendly, responsive, and helpful. It was a pleasure dealing with such a responsible and welcoming person. We’ll definitely come back again!

Private room in Winchester

5 out of 5 average rating, 3 reviews

Blewegrass Apiary

NayaraRating, 5 stars23 months ago

Absolutely zero complaints. Curt was accommodating and went above and beyond what was expected. His kids are also wonderful and the dog too! We won’t be staying anywhere else, if we go back to Kentucky. Thank you, Curt and family!

Cabin in Clay City

4 out of 5 average rating, 8 reviews

Hot Tub, WiFi & Pet-Friendly - The Ridge at RRG

EdRating, 5 stars5 months ago

Clean little Cabin, felt right at home. Hot tub is a nice addition to this place. Responsive host! Best margarita I’ve ever had at the Mexican place right in town. Would definitely stay again. The only downside is that the upstairs loft is only like 3ft tall, had to army crawl around up there lol. Perfect for kids tho.

5 out of 5 average rating, 74 reviews

*2Rm Farm Cottage*King Bed*5min DT Winchester

DennisRating, 5 stars3 days ago

Enjoyed our brief and peaceful overnight stay. It was a good and convenient location for our purpose. Appreciated Amanda’s response to our request.

Cabin in Clay City

Near Red River Gorge, cabin with fire pit & hiking

AshleyRating, 5 stars1 month ago

We had such a wonderful stay at this adorable house! The location was perfect—morning coffee on the front porch with the sunrise and relaxing evenings on the back porch soaking up the afternoon sun. The fire pit was such a cozy touch for the cooler nights, and we appreciated the neatly stacked split wood ready for use. The house itself was clean, comfortable, and had everything we needed. The host went above and beyond by offering us a late checkout on Easter morning, which made our departure so much more relaxed. One of the biggest highlights for our kids was the river just down the street—they spent hours splashing and playing in the water. During our visit, we explored the rail car experience in Versailles, hiked to Natural Bridge, and visited Creation Falls at Rock Bridge—each outing was an adventure. This stay was exactly what we needed, and we’d definitely come back!