Holiday rentals with breakfast in Shelby County

Parkside Retreat

Situated off of a parkway with mature trees lining the street, this parkside retreat is close to most everything. We are a short drive to Churchill Downs, Downtown, the Airport. Our home sits on one of the most beautiful streets in the entire neighborhood. We are 7 houses from Iroquois Park. It is terrific for walking, hiking, or just having a picnic. We have a privacy fence with a jacuzi tub on the deck. Many updates make this home the perfect choice to relax after a day of fun activities

Country Cottage in Horse and Bourbon Country

This completely updated cottage is located on a scenic byway voted one of the ten best scenic drives in the United States, on which you will see thoroughbred farms for which Kentucky is famous. Keeneland and the Kentucky Horse Park are within 20 minutes. There are 4 distilleries within 10 miles, 11 within 30 miles, and 23 within an hour’s drive. Two bedrooms, new kitchen, new bathroom, washer and dryer, covered porch, deck, air conditioning, wifi, cable TV, and ample parking. Relax and enjoy!

Captain's Cabin: Bourbon Trail, History & Romance

Your own log cabin on a wooded hillside with gourmet breakfast served to your door (on weekends)! It's been the location for 5 movies, including Lifetime! Period furnishings and modern conveniences make this an unforgettable retreat. A massive stone fireplace creates a quiet ambiance. Watch wildlife by the lake, creek or from back porch swings. Comfy bed, luxury sheets, high-speed internet, bluetooth stereo and special touches make your stay magical! Ask for Cooking With Bourbon Experience.

Highlands Carriage House

Secluded Retreat in the Heart of the Highlands! Perfect for DERBY! Our carriage house is perfectly located in the heart of all Louisville has to offer. We are only steps from the finest dining, entertainment, pubs, shopping, parks, and coffee in Louisville. Bustling and eccentric Bardstown Road is only half a block away, yet the Carriage House feels secluded and very private. It is located 5 miles from Churchill Downs, 7 miles from the airport, and 2 miles from downtown.

The Nicholson Guest House

Stay in a Charming Historic Cottage Experience a piece of history in this beautifully preserved 1830s cottage, located in the heart of downtown Bardstown—just steps from restaurants, shops, markets, local events, and nightlife. As the Bourbon Capital of the World, Bardstown offers many distilleries where you can enjoy tastings and tours of exceptional bourbons. We also offer electric bicycle rentals—perfect for exploring town and beyond. Contact me directly for details.

Sunny Clifton Loft

Recently renovated studio apartment with loads of natural light, steps from award-winning local restaurants, bakeries, bars, and housed above our independent record store. We do our best to AirBnB ethically & responsibly.. Revenue from this unit helps to 1) keep on-site residential rents affordable & increase-free 2) maintain the historic building & protect it from outside development while 3) help us steer our future as a brick and mortar independent business.

Trendy Tiny Home w/ King Bed Loft

Unique experience in style! Enjoy a weekend or an extended stay at this charming carriage house just walking distance to popular restaurants, breweries and local shops. The location is perfect! Inside you'll find a fully equipped kitchen, bathroom, living room with a 55" smart tv, a dedicated work space/desk and a king sized bed in the loft. Guests will have privacy with self-check in smart locks and a dedicated parking space. We can't wait to host you!

COZY! Minutes from Louisville. No cleaning fees!

NO CLEANING FEES!Relax in this modern yet cozy space. (2)Queen beds/bedrooms. NOTE: We too reside in upper level but will not invade your privacy. NO SHARED LIVING SPACE. 6 minutes to 2nd St bridge/65S to downtown Louisville or 2 minutes to East End Bridge (265E) to Louisville LOU (SDF) Airport 20 min CHURCHILL DOWNS 21 min Highland Festival Grounds/Ky Expo Ctr 18 min LOU Waterfrnt 12 min KFC YUM Ctr 12 min Ky Kingdom 16 min

Highlands Lower Level Studio Guest Suite

Private, well-lit, entrance is in rear of home. The space is approx. 600sq. ft. There is a gas fireplace, 42" HD TV w/Netflix & Amazon Prime. Kitchen has Keurig coffee maker, convection oven, inferred glass top burner, microwave, refrigerator/freezer w/ice, washer/dryer& a large marble shower, with heated floors in the shower room. Also space equipped w/ Medify air purifier w/H13 true Hepa medical grade filter.