Vacation rentals in Shelby County

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Top-rated vacation rentals in Shelby County

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Guest favorite

A red barn stands alongside silos against a cloudy sky, while a gravel driveway leads to the building. A large tree provides shade near the barn, and the green landscape complements the rural setting.

Farm stay in Whiteland

4.89 out of 5 average rating, 568 reviews

The Vintage Farmhouse

Charming, full sized apartment w private entrance located on 2 acres in a beautiful country setting 10 minutes from the city. 840 sq ft accommodates up to 7 people. Pet friendly, happy to share our fenced yard w your pets. Full kitchen, washer/dryer, free Wi-Fi, smart TV. Owner on site. 30 min. from downtown Indy, Indpls Intl Airport or Indpls Motor Speedway. PARKING FOR TRAILERS/UHAULS ETC. 6500 sq ft fenced yard w pizza oven available for gatherings, addtl fees apply. Inquire before booking

Top guest favorite

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.

Apartment in Fairland

4.98 out of 5 average rating, 153 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.

Top guest favorite

A cozy sleeping area features a queen-sized bed dressed in a decorative quilt with accent pillows. A floral painting adorns the wall above the bed, while a bedside lamp provides soft lighting. Drapes frame the window, allowing natural light to filter in.

Guest suite in Greenfield

4.95 out of 5 average rating, 237 reviews

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.

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.

Apartment in Shelbyville

4.85 out of 5 average rating, 74 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 favorite

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, 22 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

Guest favorite

A corner sectional sofa in neutral gray is positioned against a light-colored wall, inviting relaxation. A round wooden coffee table occupies the center, complemented by a patterned area rug. A colorful wall art piece and a small potted plant add character to the space, with a blue door visible in the background.

Apartment in Greenfield

4.74 out of 5 average rating, 23 reviews

The Riley in Historic Greenfield

Our place is recently renovated and walking distance to all of the amazing amenities Greenfield has to offer. Within half a mile of our place you will find beautiful Riley Park, a FREE community Splash Pad, a just renovated public pool with waterslides, the historic Old Log Jail Museum, the famous James Whitcomb Riley Boyhood Home and Museum, and all of the locally owned eateries and boutiques of downtown Greenfield. Start or end your days with a walk on our serene 5.6 mile paved Pennsy Trail.

Top guest favorite

A cozy living area features a sectional sofa with colorful throw pillows and an ottoman. An elegant clock adorns the wall above a decorative fireplace. A television is mounted opposite a large window, partially covered by patterned curtains. A light rug complements the hardwood floor.

Home in Greenwood

4.98 out of 5 average rating, 202 reviews

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.

Guest favorite

The exterior of a charming home showcases a grey facade with white trim. A vibrant red front door stands out, complemented by a covered porch and steps leading to a walkway. Lush green grass surrounds the property, creating a welcoming entrance.

Home in Greensburg

4.94 out of 5 average rating, 84 reviews

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!

Top guest favorite

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, 159 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!

Top guest favorite

Apartment in Indianapolis

4.98 out of 5 average rating, 405 reviews

Enjoy Comfort & History! - Suite w/ Private Entry

We look forward to welcoming you to a private suite that is the guest quarters in our home. You’ll have a private entrance & 3 rooms to yourself. There’s a living room with a table and chairs, a bedroom with a queen-size bed - nightstands, dresser and closet space with hangers for your use - and a newly remodeled full bathroom. There’s also a kitchenette in the hallway which is an antique Hoosier Cabinet equipped with a microwave, mini-fridge, coffee pot, and hot water pot.

Top guest favorite

An expansive yard is featured, bordered by mature trees and lush grass. A concrete driveway leads to the charming bungalow-style suite on the right, showcasing a well-maintained exterior with traditional features. A neighboring structure and a natural landscape complete the tranquil country setting.

Guest suite in Indianapolis

4.92 out of 5 average rating, 153 reviews

THE CUMBERLAND/Indianapolis, Indiana

"Country Living with City Convenience" 15 minutes from the town of Greenfield 15 minutes from The Academy Volleyball Club 23 minutes from Gainbridge Fieldhouse / Lucas Oil Stadium / Convention Center 25 minutes from downtown Indianapolis 28 minutes from Ruoff Music Center 29 minutes from Indianapolis Motor Speedway 30 minutes from Clowes Memorial Hall (Butler University) 31 minutes from Indianapolis International Airport 35 minutes from Grand Park Sports Campus

Guest favorite

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.

Apartment in Shelbyville

5 out of 5 average rating, 10 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.