Cottage holiday 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.

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!

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. With a pool, hot tub, and putting green there is plenty to do to unwind. Guests return year after year. This property is located on the riverbank. You may encounter bugs while enjoying the outdoors. We conduct regular exterminations to reduce encounters. You will also enjoy the songs of many birds, glow of lightening bugs, and seeing the stars.

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!

Cottage on the Bourbon Trail

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 June-Sept. We have recently also installed a Tesla High Powered Wall Charger w/60amps. We’d love to have you!

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!

Country Cottage -2 bedroom in Woodford County, Ky

Relax with the whole family at this quite charming country cottage. Private driveway. Large yard. Front and back porch areas. Six miles from and major interstate 64. Local site seeing areas within 10 minutes or less. Buckley Sanctuary, Woodford Reserve, Castle & Key Distillery, Glenn’s Creek Distillery & The Stave restaurant. Also, 20 minutes to State Capital, downtown Frankfort, The Vietnam Memorial and 30 minutes Keeneland Racecourse, Lexington. Also, 12 miles from 127 yard sale event.

Cozy Tree House @ Herrington Lake near Lexington

Looking for some time away to find your zen again? Looking for a blissful lake retreat with friends? This A-frame Treehouse at Herrington Lake, is just 40 minutes from Lexington, KY! Enjoy your coffee on the deck with beautiful lake views! Centre and Asbury parents...make my home your home away from home! My home provides single floor accessibility, with flexible bedding options! For Moms and girlfriends looking to put themselves in Time Out for a bit, you've found the perfect spot!

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.

Bourbon Trail Cottage | Walk Downtown | Keeneland

Escape to this charming Bourbon Trail cottage, just a short walk to downtown Versailles and minutes from Keeneland. Enjoy local shops, restaurants, and easy access to top distilleries. Tucked on a private drive, this peaceful retreat offers the perfect blend of convenience and relaxation for bourbon getaways, special events, or a quiet escape. Spend your evenings by the firepit with a glass of bourbon and your mornings enjoying a scenic walk through the park into town.

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.