Holiday houses in New 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).

Value · Location · Walkability

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.

Location · Value · Bathroom

The Loft at East Main

Welcome to your home away from home! This newly built upstairs apartment offers modern comfort with a small-town feel. The apartment includes a full kitchen, private bedroom, ensuite bathroom, and on-site laundry—everything you need for a comfortable stay. Perfect for business or leisure, you'll enjoy a clean, inviting space in the heart of central Indiana. The primary guest must be 25 years or older to reserve this property. Please see House Rules for details. We look forward to hosting you!

Family · Location · Parking

Entire home in Greenwood near shopping. +Pets

Modern home with room for the whole family. Less than 5 min from food, shopping. 26 min to downtown & airport. Full of personality w new appliances, furnishings, flooring, art, games/activities. 2 queen bedrooms, full bath, queen sleeper sofa & queen air mattress. Kitchen, living room, washer/dryer, Wi-Fi/smart TV. Books, games/activities. Pet-friendly fenced yard on pond—cozy, private & relaxing. I have rental cars at Greenwood & Indianapolis Airport throughTuro - please inquire for the link.

Family · Value · Comfort

Tiny Home, Big Charm! | Hot Tub, Blackstone Grill!

The Sunny Door Cottage | Tiny Home, Big Charm Step through the cheerful yellow front door and into a space of relaxation and simple luxury. Originally built in 1886, this freshly renovated 700 sq ft tiny home blends modern updates with timeless charm. Inside, you’ll find touches of the past like an exposed brick chimney stack paired with updated appliances and a cozy sliding barn door to the bedroom. The Sunny Door Cottage invites you to slow down, snuggle up, and fall in love with Franklin.

Location · Family · Bathroom

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.

Family · Value · Parks

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.

Location · Family · Hospitality

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

Family · Value · Kitchen

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

Family · Location · Accuracy

Entertainer's Dream w/ Pool and Games

You won't find a more well equipped home in the area than you will at Hometown Hideaway. Hometown Hideaway is luxury at its finest with 4 bedrooms, 2.5 baths, 2 separate living spaces, plus an amazing game room with pool table, 65" Smart TV, shuffleboard, and plenty of seating. Don't forget the fenced backyard with private heated pool and seating galore for you and all of your guests. Plenty of room for rest and relaxation indoors and out.

Family · Value · View

Private, one car garage, hot coffee

Welcome to Robin's Nest, my cozy, modern, open-concept home in Indy! This inviting space includes 2 bedrooms, 1 bathroom, and 2 queen beds. Enjoy amenities such as a coffee bar, fire pit, and workstation. Let your fur babies run free in my fully fenced-in yard. You’re in close proximity to Lucas Oil, the Convention Center, and Gainbridge Fieldhouse, Murat, and many major hospitals are in a 10 mile radius.

Family · Location · Cleanliness

Greenwood Luxury 1BR Apt Pool and Gym

Enjoy a relaxing stay in our warm and comfortable 1-BR, 1-BA apartment. Perfect for couples, solo travelers, or business guests, this inviting retreat features a fully equipped kitchen, spacious living area, and private patio. Take advantage of community amenities including a pool, fitness center, dog park, and walking path while staying close to shopping, dining, and downtown Indianapolis.

Decor · Cleanliness · View