Cottage holiday rentals in Lexington

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Top-rated cottage rentals in Lexington

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Top guest favourite

Cottage in Willisburg

4.99 out of 5 average rating, 70 reviews

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.

Top guest favourite

Cottage in Wilmore

4.98 out of 5 average rating, 248 reviews

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.

Top guest favourite

Cottage in Salvisa

4.97 out of 5 average rating, 134 reviews

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!

Top guest favourite

Cottage in Harrodsburg

4.94 out of 5 average rating, 179 reviews

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!

Top guest favourite

Cottage in Lexington

4.93 out of 5 average rating, 157 reviews

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.

Top guest favourite

Cottage in Danville

5 out of 5 average rating, 174 reviews

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!

Top guest favourite

Cottage in Lawrenceburg

4.94 out of 5 average rating, 124 reviews

Bourbon Barrel Cottages #2 on Ky. Bourbon Trail

LEAVE THE CLEANING TO US! Kick back and relax in this calm, stylish space in the center of Kentucky’s Bourbon Country. Enjoy wildlife and nature in one of our 5 two bedroom cottages. Each sits on two acres. Perfect retreat for couples traveling together or individuals looking for privacy and quiet. We’re located directly between 4 of the biggest bourbon distilleries on the trail and 20 minutes from anything you’d like to see and do! **There will be a $500 for smoking inside of the cottage

Superhost

Cottage in Stanford

4.75 out of 5 average rating, 28 reviews

Gardenside Cottage Arcadia Farm

Welcome to the peaceful, quiet, and serene Gardenside Cottage located inside the private gates of Historic Arcadia Farm. Escape from the rush of life to our newest guest cottage perfect for a small family, a group of friends, or just a personal getaway. Within a short walk from the historic Shelby Manor, you will have hiking trails, scenic walks, and nearly 700 acres to explore. The cottage is equipped with all of the essentials but without cable TV and internet, you can totally unplug.

Guest favourite

Cottage in Lexington

4.96 out of 5 average rating, 67 reviews

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.

Top guest favourite

Cottage in Pleasureville

4.99 out of 5 average rating, 209 reviews

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.

Guest favourite

Cottage in Frankfort

4.92 out of 5 average rating, 113 reviews

2 BR Cottage on the River

Nestled in the woods on the edge of the KY River, this peaceful two BR, 1½ BA home has been newly renovated & resides right in the heart of the KY Bourbon Trail & Horse Country. Willy’s Whiskey River Retreat is a cozy cottage that sits on a half acre of land. Blending modern conveniences with southern charm, character & history, this cottage is only a 10 minute drive from Castle & Key Distillery & Woodford Reserve.

Top guest favourite

Cottage in Versailles

5 out of 5 average rating, 28 reviews

Cozy Cottage Downtown Versailles

Rose Hill Cottage, built in 1877, sits in the heart of the Rose Hill Historic District of Versailles, KY. Enjoy your best night's rest with our hand-selected luxury bedding. Take a soak in the original, restored claw-foot tub. Relax on the porch while you sip your morning coffee. With the best of the old and the new, a stay at Rose Hill Cottage is sure to transport you back in time. Breakfast is included.