Holiday rentals in Shelby County

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Top-rated holiday rentals in Shelby County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
Barn in Shelbyville
5 out of 5 average rating, 9 reviews

Backyard Barndominium

This memorable place is anything but ordinary. You’ll be staying in your own 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. Out the west of the building you’ll be looking at 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, pickleball courts, splash park and more! Beautiful!!

Top guest favourite
A two-story building is positioned amidst a grassy yard, featuring a staircase leading to a spacious second story deck. Lush greenery surrounds the premises, while a few trees stand nearby, contributing to the tranquil rural setting.
Flat in Fairland
4.98 out of 5 average rating, 157 reviews

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.

Superhost
An open kitchen and living area features wooden cabinetry and modern appliances, including a microwave and dishwasher. A red table with white chairs is positioned near a bright window, while a gray sectional sofa is situated in the adjoining living space.
Flat in Shelbyville
4.85 out of 5 average rating, 80 reviews

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.

Guest favourite
A single-story home is set within a spacious green yard, featuring a freshly painted exterior with a mix of light pastel colors. A driveway leads to a two-car garage, while landscaping includes several trees nearby and decorative pumpkins positioned at the front entrance.
Home in Shelbyville
5 out of 5 average rating, 25 reviews

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 entrance of a charming cottage features a welcoming porch with wooden railings adorned with seasonal decorations. A gravel pathway leads to the door, set against a backdrop of trees and a serene river visible beyond.
Cabin in Waldron
5 out of 5 average rating, 3 reviews

River Cottage

River cottage has a full shower bathroom kitchen it's beautifull plenty of wildlife eagles different kind of birds & animals White Rock cliff diving & hidden paradise just a few minutes away Shelbyville casino is about 15 minutes away Edinburgh outlet Mall is close by there's four kayaks & a fire pit grill you're more than welcome to them and I'd bring a fishing pole if you like to fish. The river & trees are beautiful during winter time if you just need to get away and cozy up this is it!

Guest favourite
The Charles Davis Mansion is a distinctive Queen Anne Victorian structure featuring a conical turret and ornate trim. The exterior showcases intricate details, large windows adorned with decorative accents, and a wrap-around porch surrounded by well-maintained landscaping. Seasonal decor enhances the welcoming appearance.
Home in Shelbyville
5 out of 5 average rating, 34 reviews

1898 Museum Level Victorian Staycation Experience

'An Executive Experience' - A once in a lifetime chance to ‘experience’ history while visiting central Indiana. Built in 1898 by Charles Davis at the height of furniture manufacturing in Shelbyville, IN. This 4 bedroom 2.5 bath museum caliber Queen Anne Victorian masterpiece is located in the heart of Shelbyville's nationally recognized historical district. Guests will have full private access to the property which is secured by private gated parking & externally monitored video security.

Guest favourite
The two-story home features a covered upper deck with a flag, inviting outdoor space for relaxation. The exterior is clad in a combination of siding and trim, set against a grassy landscape. Stairs provide access to the upper level, enhancing its welcoming appearance.
Farm stay in Fairland
4.96 out of 5 average rating, 161 reviews

Waters Edge Racing Stable

Built in 2013, Water's Edge is a secluded, warm, & rustic 2nd story home sit above a horse barn turned epic R.E. office w/ perhaps the best view in the county! Enjoy the sunrise over the pond from the 12'x30' deck, or the animals grazing to the south. The Farm Stay is entrmt central boasting of a lg open living room/full kitchen with a wood pellet stove for your enjoyment on those cold winter nights! Not to mention catch&release fishing, corn hole, tetherball, volleyball, or bonfire!

The living room features comfortable seating arranged around a coffee table, with a TV mounted on a modern stand. Natural light filters through the windows, illuminating the polished wooden floor. An adjoining dining area is visible, complete with a table and chairs.
Home in Shelbyville
4.62 out of 5 average rating, 29 reviews

Roomy Bungalow*2 bed*1 bath

Enjoy a peaceful stay at this conveniently located 2 bedroom, 1 bath bungalow property. *Comfortable seating and TV in living room *Bedroom 1 equipped with queen size bed *Bedroom 2 equipped with queen bed and (2) twin bunk beds *Kitchen stocked with all the pots/pans/utensils needed to enjoy making meals *Bathroom stocked with shampoo, conditioner, body wash, soap, and towels *Pack-n-play and booster chair available for kids *Laundry available in the home *Street parking

Superhost
A close-up view of a putting green showcases a yellow and white flag positioned in the hole. Lush green grass extends in all directions, with trees lining the background and a glimpse of a nearby building visible in the distance.
Home in Shelbyville
4.68 out of 5 average rating, 28 reviews

19th hole - stay awhile!

Discover serenity at our charming 2BR condo, nestled on a secluded golf course. Immerse yourself in peace & embrace the tranquil ambiance that envelops you. The fully equipped kitchen is adequate, while nearby restaurants beckon with a variety of delectable flavors. Escape to nature's embrace, where every moment invites relaxation and rejuvenation. Indulge in the perfect haven for unforgettable experiences & cherished memories that will linger long after your stay.

Top guest favourite
Private room in Fairland
4.99 out of 5 average rating, 118 reviews

Serenity Stay cozy 1-bdrm unit parking on premises

Relax at this peaceful and centrally-located one-room unit; fully furnished with private bath and entrance. The room is attached to the main house. There are two doors, both are secured. Parking in front of guest door. Please note this is a rural property, you may awaken to a rooster crowing at dawn or hear coyotes howl at the moon. The house is occupied so you may hear the sound of domestic duties on occasion or the softener regeneration during the night.

Guest favourite
A modern kitchen features sleek cabinetry and a stainless steel oven and microwave. An island with dark counter space and two black stools offers a casual seating area. Natural light enters through large windows, enhancing the bright atmosphere of this inviting cooking space.
Flat in Shelbyville
4.92 out of 5 average rating, 13 reviews

Downtown Shelbyville

This beautifully updated modern apartment sits right on Shelbyville’s charming town square, just steps from local boutiques, cozy coffee shops, and delicious dining. Whether you're here for a weekend getaway or a longer stay, you'll love the convenience: only 12 minutes to Horseshoe Indianapolis Casino, 34 minutes to Lucas Oil Stadium, 45 minutes to the iconic Indianapolis Motor Speedway, and 42 minutes to Indianapolis International Airport.

Superhost
Home in Shelbyville
New place to stay

Home Away From Home Charm

The whole group will enjoy a quaint and cozy place to stay for family getaways, or extended business travel. Shelbyville, Indiana is known for its small-town charm, historic downtown, the annual Shelby County Basketball Tournament, and Horseshoe Indianapolis, a racetrack and casino. It's also recognized for its numerous parks and community events, like the annual Shelby County Fair.

Popular amenities for Shelby County holiday rentals

  1. Airbnb
  2. United States
  3. Indiana
  4. Shelby County