Holiday houses in Whiteland

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.

Modern in Heart of Downtown-Balcony

Experience luxury city living with spectacular views from your own private balcony! The 198 on Jeff, Jammin on Jeff loft has over 60 locally owned restaurants, breweries, pubs and shops within just steps. Endless entertainment options - from concerts, a summer splash pad and pickle ball across the street. Our 1,208 square foot loft is perfect for everyone—relax in style and comfort with designer furniture, modern amenities, and sleeping space for 6 people. Lots of space for your group to enjoy!

The Loft at East Main

Be our guest at this brand-new upstairs urban apartment with small-town vibe. Located 4 minutes from I65, giving you easy access to Indy Motor Speedway, Lucas Oil Stadium and various downtown concerts and events. 15 minute drive south takes you downtown Franklin, featuring charming shops and trendy dining. The apartment boasts a full open-concept kitchen and living room, cozy separate bedroom, ensuite bathroom and on-site laundry facilities. Book your stay now to be one of our first guests!

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.

Cozy Cottage 14 mi. S of Indy In Bargersville, IN

Relax and unwind in this spacious three bedroom, one bath ranch home situated on one acre. The house is on about 1/2 the acre. The house is situated in Bargersville, Indiana in Johnson County, IN on the southern edge of Greenwood located in Center Grove Area. The garage area is not accessible. Vivint Home Security system with doorbell camera. I will email your unique code once you complete reservation. Central a/c & heat. Bedroom off kitchen has window a/c. We live about 1/4 mile away.

Lovely home in quiet and friendly neighborhood!

This charming 3 bedroom 2 full bathroom home is ready to make you feel right at home! Located just 2 minutes from St Francis Hospital, 10 minutes to downtown Greenwood, 19 minutes to downtown Indy, the home is just minutes from all kinds of restaurants, shopping, and entertainment, yet provides a tranquil retreat in a quiet, friendly neighborhood. Travel nurse? Loved one in the hospital and you want to be near? Work or internship? Just need a vacation? This is the place for you!

Farmhouse Style Home with Spa-Firepit-GameRoom

Welcome to OliveBranch—a modern farmhouse style retreat with resort-style comfort. Perfect for a family getaway, a weekend with friends, a quiet retreat, or work. ✔ Family-friendly neighborhood ✔ 20 min to Downtown Indy, 10 min to Greenwood Mall ✔ 30 min to IND Airport, 45 min to Brown County State Park ✔ Private spa, firepit, grill, and game/media room ✔ 5 Smart TVs ✔ Ultra-fast WiFi ✔ Fully stocked kitchen and bathrooms ✔ Highchair, stroller, and Pack 'n Play for little ones

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

The Country Gathering - Sleeps 4 - Greenwood/Indy

6 YEARS AS SUPER HOST!!! The Country Gathering is in the upstairs of a Carriage House that was built on the property of a large home, located on the border of Greenwood/Bargersville in Johnson County, Indiana. The Carriage House has charm and character with a wooded backyard sitting on 4 acres. Sit or swing on the beautiful covered porch while you enjoy the view of the lake and fountain or feel free to walk around the property and enjoy the park-like setting.

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.