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.

Greenfield German Cottage-minutes to downtown Indy

The perfect place for you to stay when visiting Greenfield or nearby Indianapolis. Located within 1/2 mile of I-70. Restaurants and shopping within 1 mile. Downtown Indy is an easy 20-mile drive. We offer a comfy queen size bed, comfy roll away twin bed, kitchenette, full bathroom, walk-in closet, sitting area with couch and tv, private entrance with a private drive and parking area. You can also enjoy many extra features on the property, which include beautiful flower gardens and fountains.

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

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.

Cozy Cabin Close to University 1

The Red Rabbit Inn is located just 15 mins from the Indiana University campus and just 20 mins from Nashville, IN , this architecturally designed cabin features the works of local artisans. Beautifully landscaped on a secluded, wooded pond, this cabin includes a loft bedroom with KING bed, bath, full kitchen, gas fireplace, TV & Wifi, with your own private deck, outdoor hot tub, fire pit area & gas grill. Cabin sleeps 2 guests. Located near Lake Lemon, in a beautiful serene setting.

New 2B/1B house - sleeps 5!

Stay just minutes from downtown Franklin in this cozy 2-bedroom home. It's perfect for traveling professionals, small families, or weekend getaways. Enjoy a fully equipped kitchen, fast WiFi, and a dedicated workspace—ideal for remote work or longer stays. Relax in the comfortable living room with streaming TV, or unwind outside on the large deck with a fenced yard. • 10 minutes to Johnson Memorial Hospital • 30 minutes to Indianapolis • Close to local shops, dining, and events

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.

Historic Meadowdale Farm

New Construction! Entire Private Unit located in our Barn, now with a private fenced yard. Relax with the whole family at this peaceful place to stay. Our property is a quiet rural area, away from the hustle and bustle of the city, but still within 15-20 minutes of city life and shopping. Your private unit is located in our brand new pole barn on our historic farm. It is a lower level unit that sleeps 4 and has 1 bedroom and 1 bath.

The local Speakeasy

This unique place has a style all its own. Enjoy the old fashioned bar and kitchen space with all the copper features! Everything is custom made by hand here. Although it has its quirks, you'll never stay somewhere like it again. Within 1 block away : two restaurants, three bars all on the public square Within a 10 min drive: Horseshoe Casino and Horseshoe Horse Racing