Cottage vacation rentals in Lexington

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 2 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.

Country Cottage

Relax in a personal getaway or with your family at this peaceful place. Our farmhouse cottage is located on the rolling hills of our family cattle farm. It has an easy access driveway w/ample parking & outdoor space. It is about 15 minutes from I-75 which makes the interesting attractions of Berea & Richmond convenient & makes Louisville, Ky Horse Park, Lake Cumberland & Red River Gorge within a 1-2 hour drive . In addition we have another listing on the property... Serenity Cabin.

Location! Hot Tub | Comfy Beds | KY Horse Park

Stay in a 1920s "American Four Square" home in the cutest part of downtown Georgetown! New HOT TUB, a fully STOCKED kitchen, Blackstone gas grill, wonderful outdoor spaces, private deck/yard with a fire chimney (wood provided). All the AMENITIES of a clean, comfy home while visiting the bourbon trail, Kentucky Horse Park, ARK (33mi), Lexington concerts, college student visits & more. Guests love our 5-star "𝐠𝐮𝐞𝐬𝐭 𝐟𝐚𝐯𝐨𝐫𝐢𝐭𝐞" approach. We're 100% hospitality value-driven hosts!

Springwood Cottage in the heart of the Bluegrass.

Set adjacent to a Thoroughbred horse farm, this 2 bedroom, 2 full bathrooms, with central common living area cottage was completely renovated in 2018. It comes complete with modern touches and high end finishes. The property is located on a small lane and is quiet and peaceful. Visit nearby Midway, Kentucky, a charming small town with restaurants and shops. The cottage is 8 miles from Ky Horse Park, 12 miles from Keeneland and Lexington airport and 11 miles from downtown Lexington.

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

Tiny House Farm Stay on One Goat Farm

This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery. Located in the heart of an Amish community. We breed, show and raise registered myotonic goats. We have a fall and spring kidding season so if you book during that time, expect to see baby goats frolicking in the fields. The cottage is on a functioning farm with horses, cats, goats and a donkey. We offer overnight housing facilities for your own equines as well.