Holiday rentals in Shelbyville

Cheerful & cozy farmhouse 2 bedroom home

Kick back and relax in this stylish space that is right down the street from Old Greenwood & less than 20 mins to Downtown Indianapolis. This tastefully updated home exudes "peaceful and cozy" w/ 2 bedrooms w/ brand new luxury king sized mattresses, 1.5 baths w/ walk-in tile shower, charming living room w/55" TV, Fiber internet, front load washer and dryer, dining table for 4+ bar seating, and a tranquil backyard space that is fully fenced, (dog friendly for an extra $75 cleaning fee, NO CATS).

The Nigh Place, Studio Apartment, King Bed, 55"TV

Welcome! Enjoy the country views from your exclusive second story deck or relax inside of your isolated, spacious, and peaceful studio apartment. Complete with a King size bed, loveseat, recliner, 55” TV, full kitchenette, walk in closet and private bathroom. Updated, clean, and secure. Arriving late? Solar and motion detector lights along with a lighted electronic key pad for ease of access. Please note there are 23 steps with rails on both sides and a landing area half way to the apartment.

Elevated Wilderness | Mindful Retreat | 2 Kings

Executive Forest Sanctuary/2 King Beds, Hot Tub & Trails Escape to an architectural masterpiece set on 40 private, wooded acres. Designed for professionals, couples, and active adults seeking a high-end nature reset, Cabin Porch Paradise balances complete seclusion with proximity to Southern Indiana’s best destinations. Whether you are unwinding in the spa amenities, working remotely via high-speed fiber, or exploring the surrounding lakes and state parks, this is your ultimate ridgetop retreat.

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.

Charming Spacious Get Away

Experience the beauty of our newly remodeled home, steps away from the Bear Chase Golf Club. With a beautiful front yard view of the golf course, and a spacious back yard. Minutes away from local attractions & delectable restaurants. Our cozy home is perfect for families, and homebodies traveling for work. Come make treasured memories in our Charming Spacious Get Away. You are only: 8 min away from Blue River Memorial Park 7 min away from Horseshoe Casino 30 min away from downtown Indianapolis

The Rosie Roots - Cozy House & Pet Friendly

Welcome to our cozy & pet friendly 3 bedroom 1 bathroom house located in the heart of Greenfield, within 5 min to local shops & dinning and I-70. Downtown Indianapolis is a short 25-minute drive away, you'll have easy access to all the city's top attractions, including the Gainbridge Fieldhouse, Lucas Oil Stadium and many more. Our home is the perfect choice for guests who want to be close to all the action of the city while still enjoying the comfort and convenience of a charming small town.

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.

Charming 2-bedroom home on Greenwood bike trail

Cozy up with the whole family in this lovely two-bedroom, one-bathroom home. This stay includes a king and queen bed, with a TV in each bedroom. Grab a bite to eat at one of the many local restaurants or whip up your own meal in the fully-stocked kitchen. A dishwasher, microwave, air fryer, Keurig, pet bowls, and toddler dishes/utensils are included. Be sure to take advantage of the fenced-in backyard, fire pit, and gas grill. You will find a treadmill, elliptical, and weights in the garage.

Cabin on the Ridge: The Sequel

Welcome to the area's first new construction short term rental tailored for you, the guest. This contemporary cabin is nestled in the woods right in the heart of Amish country. This is the perfect destination for those who want to getaway yet enjoy the unique beauty of Historic Downtown Madison (25 minutes) recognized as "The prettiest small town in the Midwest" or chase waterfalls at Clifty Falls State Park (25 minutes). •Fast wifi •Roku TV •Keurig (K-Cups Available)

Modern Nashville Home in the Woods

Welcome to Plāhaus — a modern retreat tucked into the woods of Brown County. #1 Most-wishlisted Airbnb in Indiana per Airbnb Designed for solitude, relaxation, and connection with nature, Plāhaus blends modern architecture with peaceful surroundings. Take in the views from the balcony, gather around the firepit, or explore nearby Nashville’s shops and restaurants. Perfect for romantic getaways, family escapes, or simply recharging from everyday life.

Cozy Tiny House Nestled in the Trees

Take it easy at this unique and tranquil getaway. In a charming tiny house surrounded by trees and birdsong, you can unplug and relax without going too far off the beaten path. Only a 15 minute drive from downtown, we’re conveniently located between Fountain Square, Irvington, Beech Grove, and Wanamaker. Curl up with a cup of tea and a good book, sit on the patio and watch for deer, or take a walk around our fledgling 9-acre permaculture farm.

Reflections of Home

Kick back and 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.