Holiday houses in North Middletown

Near to EKU; discounts to 10%

Located 5 minutes from I-75. Newly renovated basement apartment perfect for solo travelers, friends or couples and is pet friendly. Take it easy at this country setting and enjoy the pool. Convenient to EKU, stay after a day at Keeneland, exploring the Bourbon Trial, concerts or just a peaceful and relaxing getaway. Available small hot tub on request. Guest space has own entrance and is separate and independent from host’s space. 5-10 minutes restaurants, groceries, gas, drug stores and banks.

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!

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.

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.

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.

Carriage House

Unwind with the spacious area this apartment has to offer. It is located on a working horse farm above the shop, in the renowned Bluegrass region of Ky. At Houstondale you can stroll to the barn and visit the horses or hide away in your space and relax. The KY Horse Park is a 22 minute drive, Lexington is 25 minutes and you are 30 minutes from horse racing at Keeneland Race Track. Even with the remote feel you are only 1 mile from Walmart, shops, and downtown Paris.

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.

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)

Paradise Inn B&B - Lover's Suite

The only B&B in Kentucky with an ‘Eiffel Tower’ view! Paradise Inn B&B is a unique penthouse suite atop "The World's Tallest Three Story Building" (from Ripley's Believe It or Not!) with exquisite oriental decor from the far East. The unbeatable hospitality is provided by your host and the owner, Lee Nguyen. This stay includes a $25 gift certificate for Paradise Cafe - Asian fusion and Pho restaurant located on the first floor.