Holiday houses in Whitestown

Guesthouse in Meridian Kessler

A cozy living area is highlighted by a three-bulb brass chandelier above a tan sofa, complemented by a wooden table. The wall features an arrangement of framed mirrors in gold and silver tones, while a doorway leads to other areas of the carriage house.

4.99 out of 5 average rating, 250 reviews

Charming Meridian Kessler Carriage House

Second floor carriage house in historic Indianapolis neighborhood. Renovated and with original architectural details like the hardwood floors. This cozy space is perfect for one or two people looking for a convenient midtown Indy location. Safe walkable neighborhood close to many restaurants. We've made the space a beautiful home away from home - lovely linens, fiber wifi and an excellent coffee machine. Like our space, but aren't coming to Indy? Message and we'll send you the shopping link.

4.94 out of 5 average rating, 18 reviews

A charming two-story home features a gray exterior with white trim and a welcoming front porch. Lush greenery and landscaped flower beds surround the entrance, complemented by a flag gently waving in the breeze. The front yard is spacious, enhancing the inviting atmosphere.

Home in Whitestown

Downtown Whitestown, King Suite & Pool

King Suite • Private Pool • Pet-Friendly Charming Whitestown stay with a king suite, private fenced pool, BBQ grill, firepit, and walkable access to Moontown Brewing Co., LA Cafe, Greek’s Pizzeria, and more! Steps from Big 4 Trail and Main Street Splash Park with tennis, pickleball & basketball courts. Includes full kitchen, fast Wi-Fi, Smart TV, washer/dryer, and free parking. Pets welcome! Perfect for couples, solo travelers, or families looking to relax or explore. Close to I-65 and I-465

Guesthouse in Carmel-by-the-Sea

An aerial view showcases a sprawling estate set on over 13 acres, featuring a landscaped yard with manicured grass. A large pond is visible in the background, surrounded by trees and established gardens. The elegant architecture of the buildings complements the serene outdoor environment.

5 out of 5 average rating, 19 reviews

Carriage house on 13+ acre gated estate property!

A private country escape in the heart of the suburbs on a 13+ acre gated estate property with old world charm! Accommodations include a semi-attached carriage home w/dedicated garage parking, fully equipped kitchen, W/D, access to commercial style fitness center, indoor half bball court with pickleball & plenty of outdoor living and areas to explore. -15 min to Grand Park -30 min or less to Lucas Oil/Gainbridge/IND/Speedway -10 min to Carmel Arts & Design District -10 min to Zionsville Village

Guest suite in Indianapolis

A landscaped garden area features stepping stones leading toward a green pathway. Lush plants and small yellow ornaments are visible, framed by trees and greenery. A decorative figure is placed among the stones, providing an inviting touch to the natural setting.

4.86 out of 5 average rating, 376 reviews

Garden Flat/Parking/WasherDryer/Close 2 All Things

Relax & unwind in our private Garden Retreat. Our MCM home was built in 1954 and is a gem hidden in the city. Modernized without comprise to the history. Acres & acres of trees and wildlife to enjoy. Minutes to Newfields Art Museum and Downtown Indianapolis. Minutes to the quaint area of Broadripple and many of the best locally own restaurants and pubs in the city. Close 2 Butler & Marion Universities & IUPUI Campus. And the beautiful & historic homes of Meridian Kessler are seconds away

4.91 out of 5 average rating, 87 reviews

An inviting living area features a comfortable, light blue sofa adorned with soft pillows. A stylish floor lamp stands beside the sofa, illuminating the space. Two framed mountain landscape prints are displayed on the wall, complementing the airy atmosphere. Natural light streams through the window.

Apartment in Zionsville

Spacious Zionsville Condo 1BR w/ Balcony

Spacious and modern one bedroom, one bathroom in a luxurious Zionsville complex in Indianapolis, IN. A vibrant and walkable area complete with an open-plan living & dining area, fully-equipped kitchen, comfortable bedroom, and sleek bathroom. This stunning and cozy space has everything you need to thrive. Located in the heart of the city's vibrant neighborhood with top-notch amenities, including a fitness center, swimming pool, grill area, and fire pit. Your home away from home in Indianapolis!

Guesthouse in Indianapolis

A cozy living area is presented, featuring a comfortable gray sofa and an armchair with a patterned fabric. A wooden coffee table stands at center, while a light fixture and an artwork are included on the walls. Natural light filters through the white blinds of the window.

4.97 out of 5 average rating, 386 reviews

Hidden Orchard Guest Cottage

Enjoy your stay at our comfortable cottage, tucked away in a quiet neighborhood off the White River (10 min. from downtown & Broadripple; less than 5 min. drive from Newfields, 100 Acre Woods, and Butler University; AND walking distance to the Fitness Farm). Feel at home in this fully furnished cottage, with its up-to-date kitchen, cozy bedroom and tech-friendly living room, equipped with hi-speed Wi-Fi, Netflix and YouTube TV. There’s also a private patio with a fire pit for you to enjoy!

4.94 out of 5 average rating, 125 reviews

A tranquil fire pit area features six wooden chairs arranged in a circular layout around a stone fire ring. The setting is surrounded by lush greenery, with the soft glow of sunset visible in the background.

Home in Whitestown

Florence Cottage~Modern Country

Relax with the whole family at Florence Cottage. Brand new home- quaint, quiet, and a great mix of country charm with stylish design. The house offers 4 bedrooms, 2 full bathrooms. The master suite has its own spacious master bathroom. Bedroom 2 and 3 are furnished with queen beds. Bedroom 4 offers a bunk bed. The home sits on an acre with stately mature trees, a fabulous front porch to take in the sunrise & then a new deck overlooking the large back yard boasting amazing sunsets at night!

An open-concept living space features a modern kitchen with a white countertop and sink in the foreground. A comfortable seating arrangement is visible, including a black sofa, a red accent chair, and a neutral-toned rug. Large windows allow natural light into the area.

4.82 out of 5 average rating, 28 reviews

Luxe Escape Near DT Indy

Welcome to your modern retreat in Whitestown, Indiana! This brand-new 2-bedroom, 2-bathroom apartment offers a luxurious yet comfortable stay for up to 5 guests. Thoughtfully designed with spacious rooms, and premium amenities, for a relaxing getaway. Each bedroom is furnished with lush queen beds, and a rollaway bed ensures extra flexibility for larger groups. The apartment also features large walk-in closets, a private patio, a dedicated workspace for remote work, and upscale bathrooms.

The living room features a comfortable blue sofa accented with bright yellow pillows, accompanied by an orange armchair. A coffee table sits on a geometric-patterned rug. Natural light enters through sliding glass doors leading to a balcony, while a large TV is mounted on the wall.

5 out of 5 average rating, 28 reviews

20 mins DT | Sleeps 4 |Golden Sun Spacious KingBed

Welcome to Whitestown, IN— proudly hosted by TIBO Ventures. Standout Features: • Modern *1-BR, 1.5-BA* with stylish decor • Fully equipped kitchen w/ new appliances & quartz countertops • Both bedrooms king-size beds and walk-in closets for max comfort • Private balcony for relaxing Amenities: ✔ 24-Hour Gym ✔ Pickleball Courts & Pool ✔ Built-in Desk for remote work ✔ Pet-Friendly community with Dog Park ✔ High-Speed Fiber Internet ✔ Close to dining and shopping ✔ Free On-site Parking

4.86 out of 5 average rating, 584 reviews

The exterior of a two-story guest house is surrounded by autumn foliage, showcasing wooden decking with a railing. The entrance features large windows, allowing natural light to brighten the space. A pathway leads from the front, bordered by seasonal plants.

Guesthouse in Brownsburg

Cozy Guest House in the Big Woods

Guest house located in the rear grounds of main home. Sidewalk access. 20 minute drive to downtown Indy.Full kitchen & 3/4 bath. This means toilet, sink & 42" shower (no tub).Entire house can sleep 1-3. Price is for 2 guests. Add’l fees for add’l guests & pets (no pit bulls) The upstairs has a king bed & down stairs a twin futon. This area is heavily wooded so the occasional critter can be seen & there will be spiders from time to time (part of wooded living).

Superhost

5 out of 5 average rating, 3 reviews

IRIE Living-Retreat Kg 2Bd+Gym+Pool, BRAND New!

IRIE Living-Retreat Kg 2Bd+Gym+Pool, BRAND New! Discover your perfect home base in Whitestown, IN! This brand-new, modern 2-bedroom apartment is ideal for families, friends, or teams visiting Farmers Bank Fieldhouse, nearby shopping spots, or downtown Indianapolis, just a short drive away. Whether you're here for a tournament, a weekend getaway, or a business trip, you'll enjoy all the amenities you need for a comfortable, stress-free stay.

4.97 out of 5 average rating, 34 reviews

A modern living area features a large sectional sofa with soft cushions and a neutral color palette. An abstract art piece with vibrant colors is displayed on the wall. Natural light enters through a sliding door that opens to a small outdoor space.

Condo in Zionsville

Modern Design Meets Luxurious Comfort at Stonegate

Discover the perfect blend of comfort, style, and convenience in our beautifully designed 2-bedroom apartment in the heart of upscale Stonegate Village, within 30 mins to Downtown Indy. Spacious Living Area: Relax in a cozy, light-filled space with modern furnishings and 65-inch smart TV. Fully Equipped Kitchen. High-speed Wi-Fi for work or streaming. Free parking on-site. Multiple restaurants nearby within walking distance.

Popular amenities for Whitestown holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Whitestown

A bright living room features a grey sofa adorned with decorative pillows, complemented by a round wooden coffee table. Floor-to-ceiling windows are dressed in light grey curtains, allowing natural light to illuminate the space. A balcony is visible beyond the glass doors, furnished with outdoor seating.

4.95 out of 5 average rating, 64 reviews

Serene 1BR: Perfect Indy Stay

Private room in Zionsville

4.91 out of 5 average rating, 23 reviews

Comfy room w bathroom kitchen exercise near Indy!

Private room in Indianapolis

4.89 out of 5 average rating, 9 reviews

Bukky Home 1

A modern living area features two plush black sofas adorned with colorful cushions, accompanied by a sleek round coffee table. Natural light fills the space through large windows with blinds, highlighting the stylish area rug that adds warmth to the room.

4.93 out of 5 average rating, 27 reviews

Sora, The Loft

Guest suite in Zionsville

An outdoor seating area is surrounded by lush greenery, featuring a fire pit at the center. Several comfortably spaced chairs and a dining table are arranged on a gravel surface, creating a cozy environment for gatherings.

4.94 out of 5 average rating, 176 reviews

Cozy Country Guest Suite

Private room in Indianapolis

5 out of 5 average rating, 15 reviews

King Bed: Private Spa Bathroom- near downtown

Superhost

A cozy living area is showcased, featuring a vibrant blue sofa complemented by decorative pillows. A modern gray armchair is positioned nearby, with a glass coffee table enhancing the space. Natural light streams in through large windows adorned with blinds, illuminating the contemporary décor.

Apartment in Zionsville

4.71 out of 5 average rating, 14 reviews

Ziva Luxury 2BR 2BA Near DT Indy

A light-filled living area showcases a comfortable sofa adorned with decorative pillows and a soft throw blanket. A glass coffee table is positioned centrally, complemented by two round side tables. Natural light streams through the neatly framed windows, enhancing the inviting atmosphere.