Holiday rentals in Madison County

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Top-rated holiday rentals in Madison County

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Top guest favourite

Flat in Richmond

4.96 out of 5 average rating, 385 reviews

Luxury on Main / East

Head past the custom front-door painting and into an interior with original hardwood flooring. Standouts include a remote-control fireplace and subway-tiled kitchen with stainless steel appliances. A wood stove adds a warm glow to the shared patio. This 1920's shotgun-style four unit apartment building has been completely restored with all modern amenities. The Tenant House has a rich history on Main Street in downtown Richmond. Guests have access to all shared spaces I will be available 24/7 for contact via text, call, email, or in person. Information about the surrounding area and the unit will be provided. Walk to the latest downtown venues and jog round nearby parks from this location, directly across from the Richmond Visitors Center. Eastern Kentucky University is also convenient for here, while many places to eat and drink are on the doorstep.

Guest favourite

Flat in Richmond

4.91 out of 5 average rating, 133 reviews

Cozy upstairs 2bed/1 bath Apt Richmond near EKU

Cozy upstairs 2 bed apartment offers a clean comfortable stay near downtown Richmond and the EKU campus. Centrally located for ease of commuting to downtown, Wal-mart, Kroger, Richmond Centre shopping and numerous restaurants. Easy check in / check out process. Security cameras on site. Egyptian cotton towels and microfiber sheets provided. Full size washer / dryer in unit. This unit can be noisy during weekdays from 6 am to 5 pm from the granite business next door. Located 7 minutes from I-75.

Guest favourite

Flat in Richmond

4.94 out of 5 average rating, 143 reviews

Modern 2bd 2ba - Near I75, No Steps, Free Wifi

This spacious, single level duplex unit is located in one of Richmond's best neighborhoods and only 24 miles from Lexington, KY. It is perfect for a quick one or multiple night stay. With the central location of this unit, you are a short drive from all attractions! You and your guests will LOVE this luxury unit that provides stainless steel appliances, granite counter tops, memory foam mattresses, coffee bar, sectional sofa, work area, games and much more. 4 miles from I-75 2.5 miles to EKU

Top guest favourite

Home in Richmond

4.96 out of 5 average rating, 141 reviews

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.

Top guest favourite

Home in Richmond

4.99 out of 5 average rating, 187 reviews

Richmond Retreat by Raydarr Properties, LLC

Older home with lots of character located within walking distance of downtown Richmond. If you like the outdoors there is a porch with a swing, and a sitting area in the back yard with a fish pond. Located approx. 2 miles off of I-75. The driveway goes behind the house for parking, and is quite narrow. There is plenty of room in the driveway to park out front (which is also safe), if you are unable to squeeze through. The driveway side of the yard is open, so the backyard is not fully fenced.

Top guest favourite

Home in Berea

4.93 out of 5 average rating, 763 reviews

Berea Painter's Cottage

Eclectic, clean, comfortable cottage featuring original artwork, located in walking distance of Berea College Campus, Artisan Village/Old Town area, Art Galleries, Unique Shops, The Lot, Rebel Rebel, Nightjar, Sunhouse Craft, and Native Bagel. A short drive to the Pinnacles and Kayaking at Owsley Fork Lake. The location is great. A cozy patio in front of the home with a swing and a tree canopied deck in back that feels like being in a treehouse. Basic TV channels and high-speed internet.

Guest favourite

Cabin in McKee

4.97 out of 5 average rating, 405 reviews

Mountain Dream Cabin -Fish Pond+Fenced Yard+Stalls

Escape to a peaceful cabin with a wraparound porch perfect for soaking in the beauty of nature. This pet-friendly retreat features a fenced yard and space for trailer parking, plus four horse stalls available upon request. Enjoy catch-and-release fishing in the stocked pond, or explore nearby attractions: 25 minutes to Berea’s historic downtown and Pinnacle Trails, and 30 minutes to Flat Lick Falls and Sheltowee Trace. Unwind, explore, and experience the charm of our small-town getaway!

Guest favourite

Cabin in Berea

4.92 out of 5 average rating, 218 reviews

A Happy Place Cabin with magical views!

A cabin and experience like no other in Berea. Enjoy the smell of cedar, sounds of the country, amazing views of the mountains and magical sunsets! Relax in our cozy all cedar cabin that sits on a 37 acre property. Fish in the large pond, swing on the porch, and cook dinner outside on the Blackstone griddle. Located just 5 miles from town, it is close enough to find great dining options and visit all that Berea has to offer, yet far enough away to provide serene tranquility and peace.

Top guest favourite

Guest suite in Berea

4.99 out of 5 average rating, 122 reviews

The Artist's Tranquil Nest & Studio

Nestled near Central Kentucky Wildlife Reserve, The Nest offers an entire upper floor for one price with two private rooms: Chickadee’s Nest (queen) & Sparrow's Nest (king and trundle), a Gathering room with a sleeper sofa, Paris Coffee Room, bird bath (bathroom), bird perch (deck), wifi, monitor/cable in each room. Art classes are offered upon request by children's book author/illustrator, Lori McKeel, for an additional fee. Separate entrance and plenty of privacy and parking.

Guest favourite

Flat in Winchester

4.89 out of 5 average rating, 159 reviews

The River House Floor 2 Getaway, w/a river view.

Enjoy the spectacular views of the Kentucky River from this second-floor studio. Located within an easy walk of hiking trails and dining. Visit the Waterfront Grill or Hall’s on the River. A tasting at the winery just a few minutes away will sweeten your stay. For more play, kayak rental is nearby. This property is nestled on the riverbank. You will encounter bugs if you are enjoying the outdoors. We have regular exterminations, but an occasional cob web is to be expected.

Guest favourite

Home in Berea

4.89 out of 5 average rating, 159 reviews

Cheerful 2 bedroom home with parking on premises

Stay in style at this bright and newly renovated home where Old Town is only an 2 minute drive away! You'll have the whole home to yourself! amenities, including a full fenced in backyard and private driveway– all with restaurants and shops within easy driving distance.Perfect for a couple or a small family. If you’re searching for a cozy home in Berea with a great location, then look no further. Save your dates now and enjoy a vacation where the art is.

Guest favourite

Cabin in Lexington

4.83 out of 5 average rating, 602 reviews

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)