Holiday rentals in Greensburg

Historic Drees Haus, Oldenburg

Drees Haus is a charming 1870s home on the historic district walking tour of Oldenburg. Located on a quiet street, across the street from the convent wall, and next to the well-maintained village park, this brick cottage home is an example of the town's late 19th century architectural style. It reflects the German heritage of the village, with much of the artwork and furniture original to the town and surrounding area. Easy walking distance to restaurants, shops, and the Catholic church

Stay Awhile on Broadway

This newly-renovated upstairs apartment is located in the heart of Shelbyville's Entertainment and Business district. Just a short two blocks away is the Public Square, with restaurants and bars for every taste. Also within easy walking distance are the City and County Government Centers, the Post Office, two banks, an office supply and print center, and drug store. Because Shelbyville is a bustling, vibrant city, you can expect to hear the traffic sounds associated with living on a busy street.

All-Star Sport House, fenced yard, NexusPark 1mile

Welcome to our family and pet-friendly sports haven! Perfect for active families, this spacious retreat features a stadium-style family room for game-day excitement. Step outside to a fully fenced backyard with a portable badminton net and equipment, perfect for friendly matches. With room for everyone, including your furry friends, it's the ultimate getaway for sports-loving families. Book now and score a memorable stay! Less than 1 mile from Nexus Park School tennis court walkable distance

2b/2b Home in Columbus

Located just minutes from downtown Columbus, this home is perfect for solo travelers and families alike. This historic home has been updated and has all the modern amenities that one would need, including a full kitchen with dishwasher, two full bathrooms, and washer & dryer. It is a short drive to Cummins, Columbus Regional Health, Dunn Stadium, The Commons, Mill Race Park, The Miller House & Garden, Zaharakos (a historic ice cream parlor with soda fountain), and Columbus Municipal Airport.

Tree City Retreat

Tree City Retreat is a cozy 3 bedroom, 2.5 bath home made to entertain any group. Relax with the whole family at this hidden gem located in Greensburg, IN, which is conveniently 1 hour away from Indianapolis and Cincinnati. Enjoy the outdoors with a pool, fire pit, pond, walking trail, badminton, basketball, game room, and many other outdoor games. Inside, make yourself a drink at the home bar and hang out with friends in the living room where you can take in the scenic view of the pond.

Backyard Barndominium

This memorable place is anything but ordinary. We’re a mile from I74 exit. This is a 2000 square foot house with a great room that towers to 14’ ceilings. Two large bedrooms with large walk in closets for extra dressing space. View from kitchen windows overlooks a forest of 100 trees. (And we’re in town!) Fully furnished kitchen to prepare your meals. You’ll find a beautiful park across the road with miles of wooded walking trails and a lot to explore. Lots of parking. Easy access.

Super Cute + Cozy Home Downtown!

🌺5 min off I-74 🌺20 min to Batesville 🌺45 min to Indianapolis 🌺Just over an hour to Cincinnati One of the only homes of its kind in Greensburg, this 900+ sq ft home was built in 1900 and taken down to the studs in 2021. Enjoy a bath in the "soaker" tub, snuggle up with a book in the front room, or have a fire in the private backyard. The paintings through the home are done by the homeowner's grandmother. Feel like baking? Fire up the double ovens in the stunning kitchen. You're home!

Unwind Haven

This historical barn is nestled right in the heart of southeastern Indiana’s farmland. Enjoy the Crossroads of America by adventuring to local hometowns, State Parks, shops, and restaurants. Enjoy live music, museums, and other attractions by visiting three conveniently located cities. If it’s serenity that you’re searching for you’ll find that by watching our beautiful sunrises or sitting around the fire pit gazing up at the stars. You won’t forget the peacefulness of this destination.

Tree City Getaway

Our space is an upscale property blending modern luxury with small-town charm. Located in the heart of Greensburg, IN you're just minutes from local shops, dining and community attractions-while still enjoying a peaceful, private retreat. STAY-RELAX-RECHARGE Smart TV's in bedrooms & living room, washer & dryer, WiFi and clean, modern features with upscale touches. 2 bedrooms plus queen size sofa bed, 1.5 bath, full kitchen and dedicated workspace.

Tranquil Terrace with King Bed Suite

Enjoy privacy on our sunrise terrace with a view to the trees of Haw Creek - yet you are still in a modern neighborhood in Columbus, Indiana. * New Ranch Home Built in 2016 * King Sleep Number Bed Master Suite * High Speed WiFi * Open Concept Living-Dining-Kitchen Area * Disney Channel Plus, Paramount Plus, Prime Video and More * Outdoor Fire Place on Private Patio * Coffee and Tea * Full Kitchen with all Cooking Needs * Laundry

Heart of Home

Enjoy all the amenities of home in this adorable, and conveniently located duplex situated in a quiet neighborhood. This duplex unit is located within minutes of architecturally diverse Columbus neighborhoods, close to Lincoln Park ball diamonds, biking and people trails are within a mile. The area has a wide variety of local dining favorites and is also 30 minutes from Brown County state park and Nashville.

5BR Retreat w/ Private Indoor Pool In Greensburg

Welcome to your perfect getaway in Greensburg, Indiana — a spacious and beautifully designed 5-bedroom 2 1/2-bath home featuring a private indoor pool for year-round relaxation and fun. Whether you're visiting for a family trip, weekend escape, or extended stay, this home offers the ideal blend of comfort, entertainment, and convenience — all just about an hour from Indianapolis and Cincinnati.