Cottage vacation rentals in Lexington

A Romantic Getaway on the Bourbon Trail

Unwind and relax amongst the gorgeous and peaceful surroundings, or step out and explore. Enjoy this slice of raw Kentucky set on 100 acres of pristine rolling hills, creeks and forest you're free to explore. The space is completely self-contained with a large fully equipped kitchen, 1.5 bathrooms, a luxurious king size bed and a twin daybed. This piece of Central Kentucky is along the Bourbon trail, and is just 1-hour from Louisville, 40 minutes from Lexington, and 20 minutes from Bardstown.

River House - Cottage with KY River View & Access

Come relax at the peaceful river house. It feels like a retreat right on the Kentucky River with a party-sized dock for easy river access. It’s a cozy cottage on stilts with a breakfast bar on the porch and swing on the patio. Be surrounded by nature and beautiful views of the river and palisades. Tuck away in seclusion just minutes away from downtown Wilmore, Asbury University & Seminary. 35 minutes or less from LEX Bluegrass Airport, Keeneland and Shaker Village. See guidebook for more info.

Cottage on the Bourbon Trail

Newly built cottage located in the country. Enjoy amazing views from a covered front porch as you rock in comfortable rocking chairs. Fully furnished and beautifully decorated to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a kitchen for cooking if desired. Pool is behind owners residence and is shared with owners family and possibly 2 additional people. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

Paradise Cottage Enjoy lake Views and Lake Access!

Relax and enjoy! Great Herrington Lake views with lake access at Paradise Cottage! Peaceful private setting on one of the most beautiful parts of the lake. Located Mins from Multiple marinas, Bourbon trail, golf courses, Centre College/Asbury University events. 3 bedrooms, 5 beds, 2 full bathrooms, washer/dryer, newly remodeled. Sleeps 9. Includes: wi-fi, Hulu, 2 TVs, multiple decks, covered side patio, fire pit, gas grill, corn hole, kayaks and lily pad included with stay! Four parking spaces!

Retro Mid-Century English Cottage

Just minutes to Keeneland and Red Mile. You’ll be glad you found this hidden gem in the Horse Capital of the World. Close to everything but in a safe and friendly neighborhood. Within ten minutes (or less) to Keeneland, Downtown, Rupp Arena, The Distillery District, UK, Masterson Station Park, Legacy Trail, The Arboretum or a scenic drive down Old Frankfort Pike. Our cozy cottage boasts two bedrooms with queen beds, a huge back yard with privacy fence to relax in, wi-fi, and large screen tv.

Quaint cottage in the heart of Danville

Cute renovated cottage in the heart of historic Danville. Walking distance to downtown and all of Centre College. Enjoy local restaurants, the Saturday morning Farmers Market, and the amazing shops on Main Street. The Cottage is fully furnished and beautifully decorated to make your stay comfortable and relaxing. All beds are memory foam mattresses, and all linens are 100% cotton with hypoallergenic fiber filled pillows and comforters. The front porch & deck offer outdoor space to sit a while!

Bourbon Barrel Cottages 3 Ky Bourbon Trail HOT TUB

Leave the Cleaning to Us – Your Bourbon Country Escape Awaits! Kick back, relax, and unwind in a stylish, serene retreat nestled in the heart of Kentucky’s Bourbon Country. Welcome to Bourbon Barrel Cottages, where nature, comfort, and convenience come together. Each of our five private two-bedroom cottages sits on its own two-acre lot, surrounded by wildlife and natural beauty—perfect for couples, friends traveling together, or anyone seeking peace and privacy. You'll Love Staying with Us!

Bluegrass & Bourbon Cozy Cottage

Welcome to our cozy cottage in Woodford County, right on the Kentucky Bourbon Trail! Just a 10-minute walk to downtown, you'll find coffee shops, restaurants, bakeries, parks, & The Amsden Bourbon Bar. Iconic spots like Woodford Reserve, Castle & Key, & Keeneland are all within 7 miles. Though visible, the quiet cottage is tucked away with a private drive, offering a peaceful retreat. Whether you're into bourbon, horses, hiking, or just relaxing, you’ll feel right at home. Book tours early.

Life is Better On The River

Make lasting memories at this unique and family-friendly cottage on the Kentucky River. Enjoy nature at its best, along with all the comforts of home. Guests return year after year. * WiFi is sometimes unreliable. It connects via satellite, as this is the only option available in our neighborhood. WIFI Riverstar, Pw 12345678 This property is located on the riverbank. You may encounter bugs while enjoying the outdoors. We conduct regular exterminations, but occasional cobwebs happen.

Quaint Cottage in DTown Lex, 15 mins to Horse Park

• Neighboring The Legacy Trail • Walkable to Local Favorite Spots | West Sixth Brewery, County Club, The Blue Heron Steakhouse • TVs in Living Room + Bedroom • Fully Equipped Kitchen What is the Legacy Trail? It is a shared-use greenway trail that snakes its way through Lexington's iconic horse farms and green, rolling hills. This 12-mile trail starts in downtown Lexington and leads to the iconic Kentucky Horse Park. Premise ID for Local Regulations & Licensing: 15081035 dash 1

The Cottage at Montresor

Certainly one of the most enchanting, smartest places to escape to. Everything about it is just right: stay at our splendid 50 acres just minutes from Keeneland. Relax in comfort surrounded by beautiful decor - all in proportion. An unrivaled ambiance of peace & tranquility with the convenience of contemporary living. This destination will leave you wishing you could stay forever. 5 minutes from restaurants & grocery, 12 minutes from the airport & luxury shops.

Linden Place LLC

Our cabin is on gated property in the middle of Bluegrass horse country with a an indoor and outdoor private shower and sits on the back of 5 landscaped acres for maximum privacy. Close to the Ky Horse Park! Incl., YouTube TV, WiFi, deluxe king bed, & private deck overlooking pastures. Snacks, tea/coffee and breakfast items provided. Please note there will be a pet fee of $25/Nite/pet with a max weight of 35lbs. Fees will be requested after booking.