
Holiday rentals in Madison County
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Top-rated holiday rentals in Madison County
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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.

College-town Comfort
Centrally located in Richmond, KY with easy access to I-75. The house is a 6 minute drive to downtown Richmond and Eastern Kentucky University. A new park is 3 minutes away. Several grocery stores are close; 10 minute drive from restaurants and entertainment. The new Richmond Sports Complex and Lexington Sporting Club Youth Complex are an easy, short drive away. This charming house is great for a couple, two couples, or a family visiting the area! Guests breaking house rules will be vacated.

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.

Southern Charm
Centrally located to all things Richmond!! This beautiful home gives you all the warm and cozy vibes. From the time you walk in the front door, it will feel as comfortable as being home. Enjoy the fully stocked kitchen, spacious and well-appointed bedrooms, electric fireplaces in several rooms, pool table, covered back deck with grill, large backyard, Roku enabled TV's throughout and so much more. Let your family enjoy the whole home instead of booking two rooms at a hotel! See you soon!

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.

Simply sweet - Entire 1 bed upstairs apt near EKU
Simply sweet is a cozy upstairs 1 bed apartment that offers a clean comfortable stay near the EKU campus. Close to Purdy's Coffee and BBH. Centrally located for ease of commuting to downtown Richmond, 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. Stackable washer / dryer in unit. Located 7 minutes from I-75. No pets please-there’s no green space here.

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!

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.

Westwood
Stay in this newly renovated, freshly furnished 3 spacious bedroom 3.5 bathroom home in the heart of Richmond, KY. This home has many luxury features like a sunroom, granite countertops, and is walking distance to Eastern Kentucky University’s Campus. Included is a Smart TV in the living room, TVs in 2/3 bedrooms, adjustable AC/Heat, Serta Mattresses, and luxury furniture perfect for relaxing. We appreciate you staying with us, and feel free to reach out at any time during your stay!

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. Guest space has own entrance and is separate and independent from host’s space. 5-10 minutes restaurants, groceries, gas, drug stores and banks.

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)

Stunning Cedar Cabin, Hot Tub, Amazing Views!
Escape to this serene cabin surrounded by 20 acres of green hills. This cedar cabin is only 15 minutes from Richmond KY, but you'll feel like you're in a different world. Admire the nature through floor to ceiling windows, roast marshmallows on the patio with a chimenea, and melt your stress away in the Artesian Premier hot tub. Experience a peaceful stay in this quiet and comfortable retreat.
Popular amenities for Madison County holiday rentals
Other great holiday rentals in Madison County

Pinnacle Lodge now w/ Brand New Hot Tub!

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

Spacious Downstairs Apartment

Silo Mill

Davis Hollow Retreat

Charming Private Cabin on Red Haven Farm

Luxe Villa with Private Pool & Hot Tub

Cozy Corner
Destinations to explore
- Rentals with a firepit Madison County
- Rentals with a fireplace Madison County
- Rentals with a washing machine and dryer Madison County
- Cabin rentals Madison County
- Rentals with outdoor seating Madison County
- Flat rentals Madison County
- Farm stay rentals Madison County
- Family-friendly rentals Madison County
- Pet-friendly rentals Madison County
- House rentals Madison County
- Rentals with a patio Madison County
- Kentucky Horse Park
- Buffalo Trace Distillery
- Rupp Arena
- Levi Jackson Wilderness Road State Park
- Anderson Dean Community Park
- SomerSplash Waterpark
- Old Fort Harrod State Park
- Hamon Haven Winery
- Talon Winery & Vineyards
- Idle Hour Country Club
- Paradise Cove Aquatic Center
- Rising Sons Home Farm Winery
- Equus Run Vineyards
- Lovers Leap Vineyards and Winer
- Wildside Winery
- Beatty Fork




