Holiday rentals with breakfast in Southern Indiana

Action City! Extravaganza at Bardstown Rd!

In the HEART of the Highlands, this spot sits near the corner of the main strip- just steps to Bardstown Rd. A few minutes drive to anywhere in city limits! And exactly where YOU want to be! Action Packed: Restaurants, Shopping, Bars, Parks, and Church- all walkable. A surprise local GIFT CARD given with each stay! This place is stylish, chic, cozy, and extremely quiet, as double pane windows have been installed. Recently renovated, it houses all the essentials for a weekend or week long stay.

Hideaway Hollow - A Woodsy Getaway

Hideaway Hollow is a cozy, private guest suite in Bloomington, Indiana. Located on the north side, it is just fifteen minutes from the heart of downtown Bloomington, IU stadium, and an hour from Indianapolis. Nestled in the forest, the suite offers a covered porch with a private entrance, a spacious living room, a kitchenette, and a master bedroom with a full bath. Suitable for up to four guests, come to enjoy the serenity of country living, the comforts of home, and easy access to the city.

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.

Aloft

Aloft is located on the edge of the Hoosier National Forest, minutes from hiking trails and Ski Paoli Peaks. Located about 20 minutes from French Lick Resort and Casino, Patoka Lake, Marengo Cave and Cave Country Canoes. You’ll love the loft because of the country setting, nestled in the trees. The loft is very comfortable and offers peace and quite with a contemporary, calming atmosphere. The loft is great for couples, solo adventurers, business travelers, and families (with kids).

Bourbon City Loft - Free downtown parking!

If this loft is booked, please check out my other listings... https://www.airbnb.com/h/derby-city-loft https://www.airbnb.com/h/river-city-loft Spacious 950 sq. ft. loft located in the heart of downtown Louisville. Walking distance to shops, restaurants, bars and 1 block from 4th Street Live! You'll be 4 blocks from the YUM! Center, 2 blocks from the Kentucky International Convention Center, and less than 10 minutes from Churchill Downs! Free parking in a secured parking garage!

The Sanctuary 14 acres w/pond/fishing/trails/& fun

Come and enjoy a getaway from the busy world to a quiet home in the woods in Brown County, located near Nashville, IN. You can enjoy the large gathering room overlooking a beautiful pond that is surrounded by trees. Take a ride on the paddle boat and throw your fishing line in to catch catfish, bluegill, and large mouth bass. Eleven acres of trails make for a nice nature walk. In the cold , you can enjoy coffee by the fireplace that's in the large room we call, The Sanctuary.

Cozy Lakeside Cabin at Lake Lemon

Wonderful cozy home nestled by Lake Lemon, near Bloomington Indiana. Walk right next door to the Porthole for delicious pizza, stuffed breadsticks and cold drinks after an action packed day on the lake. Gather around the firepit for s’mores! Our lake home is the perfect mid-way point between IU Bloomington and Nashville (Brown County) Indiana! Catch an IU game, stay by the lake while you’re in town to visit family, or make us your home base while you explore quaint Nashville!

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.

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!

Strawbale Bungalow. Bloomington Indiana USA.

Art and book filled. Located in Bloomington Indiana. My 1920s bungalow includes two guest bedrooms with queen sized beds, down comforters, feather/down pillows, line curtains and private bathroom. The guest area also includes a garden porch, private entrance, living room and, dining area with microwave, small refrigerator and handmade maple table. NO KITCHEN. The bathroom is between the bedrooms and includes a Toto washlet bidet and EO toiletries.

Private home, one car garage, hot coffee

Welcome to Robin's Nest, my cozy, modern, open-concept home in Indy! This inviting space includes 2 bedrooms, 1 bathroom, and 2 queen beds. Enjoy amenities such as a coffee bar, fire pit, and workstation. Let your fur babies run free in my fully fenced-in yard. You’re in close proximity to Lucas Oil, the Convention Center, and Gainbridge Fieldhouse, Murat, and many major hospitals are in a 10 mile radius.