Pet-friendly holiday rentals in Madison County

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.

Downtown Charm - Walk to EKU & Parks Near I-75

Charming 4 BR/2 BA HOUSE in a quiet neighborhood in quaint downtown Richmond. Backyard patio, fire pit & Grill Walk to EKU, Restaurants, Bars, Parks & Shopping. Only 5 mins to I-75 30 mins to Lexington Airport (LEX). High Speed WIFI 2 Smart TVs - Rokus for Streaming. Sling TV & Antenna with 50 channels Sleeps 8 persons. $55 extra per person & night for parties above 4 guests. Pet Fees - $100 per pet. Pack n' Play with mattress, bassinet, high chair, toddler rails & stair gate available.

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.

Walnut Creek Retreat - King Suit - Waterfall

Charming, fully renovated 1866 farmhouse retreat with peaceful country side views, a wide creek and waterfall. King suit with lavish master bath (rain shower, soaking tub, and heated floors) Cozy Scandinavian farmhouse vibe complete with fireplace, fire-pit, and thoughtful amenities throughout. Large, fully equipped kitchen and dining space. Close driving distance to outdoor activities, charming towns, EKU, and attractions. Great for families, small groups, couples, or a solo retreat.

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.

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!

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)

Stable Suite on Farm, with view of Goats’ Stall.

Are you dreaming of the perfect farm stay? Nicura Ranch is a private farm located only 1.5 miles from I75. This stable suite is 1 of 5 suites attached to our barn, and very unique. A bedroom window looks directly into our goat’s stall. The private barn suite features a bedroom, full kitchen and bathroom. There is a private entry and free parking. The suite comfortable sleeps 2 adults. Breakfast and a glass of Bourbon included. Pet friendly/no fee

Kilday Cabin at Happiness Hills Farm

The Kilday Cabin is a cozy, Amish-built log cabin at Happiness Hills Farm, a farm and retreat center in the Appalachian foothills near historic Berea, Kentucky. It's a perfect little getaway for couples, families (with a kid or two), and small groups who want to enjoy each other's company in a beautiful setting. This cabin is one of a pair - the Moore Cabin is right next door, with a shared picnic area between.

Charming Private Cabin on Red Haven Farm

Escape to a cozy cabin tucked away in a quiet holler on our 540-acre Red Haven Farm. Surrounded by forest, creeks, and wide-open sky, this peaceful retreat is the perfect spot to unplug, recharge, and reconnect with nature—while still enjoying the comfort of WiFi when you need it. If you need more space, we also have two other rentals on the property and camping options.