Holiday rentals in Whitestown

4.98 out of 5 average rating, 42 reviews

A spacious living area is illuminated by natural light from skylights, featuring a mix of seating options, including a leather sofa and light-colored chairs. A central coffee table is positioned over a hardwood floor, and artwork adorns the walls, enhancing the room's inviting atmosphere.

Home in Westfield

Cozy, roomy 3 Bdrm Westfield home.

Come and relax with family or friends, enjoying the entire home. You will find that it is spacious and cozy; has a full kitchen and laundry room. Minutes from Grand Park, interstate access, Cool Creek or the Moon Trail for hiking, biking or walking. Dine at specialty local restaurants or franchise faves. Shopping is close by with boutiques in Carmel and Noblesville just ten minutes away. Downtown Indy is 30 minutes to Lucas Oil Stadium, Indianapolis Convention Center or Gainbridge Fieldhouse.

4.89 out of 5 average rating, 18 reviews

The living room contains a gray sofa and two striped chairs, creating comfortable seating. Natural light enters through large windows adorned with white blinds. A round area rug is positioned on the floor, while a decorative piece hangs on the wall, contributing to the room's aesthetic.

Home in Lizton

Cozy Home w/ Bar Room + Huge Yard + Coffee Station

Welcome to your home away from home in Lizton, Indiana! This charming 2-bedroom, 1-bath house comfortably sleeps 6 guests, making it perfect for families or friends. Relax in the cozy bar room or enjoy the spacious backyard, complete with a fire pit—ideal for roasting marshmallows and making s'mores. Located just 30 minutes from Indianapolis and near two beautiful wedding venues, this retreat offers the perfect blend of comfort and convenience. Experience a memorable stay in a peaceful setting!

4.88 out of 5 average rating, 65 reviews

Home in Westfield

Luxury awaits! Huge Home 4 Min to Grand Park!

Stay just 4 minutes from Grand Park in this ideal Westfield location, surrounded by restaurants, grocery stores, and more! Whether you’re here for sports, a reunion, a wedding, or a getaway, this home has it all. Enjoy 4 spacious bedrooms, 2 ½ bathrooms, a fully stocked kitchen, dining room, cozy family room, dedicated office, and on-site laundry for ultimate convenience. Treat your family or team to top-tier accommodations that raise the bar for vacation homes—message us with any questions!

4.89 out of 5 average rating, 28 reviews

A spacious kitchen is designed with light-colored cabinetry and a wooden ceiling. An island with bar seating is featured, complemented by modern appliances. Natural light fills the room, highlighting the open layout and inviting atmosphere.

Home in Westfield

Sleeps 10+/Batting Cage/Theater!

Discover the ultimate Westfield retreat! Sleeps 10+, near Grand Park, and packed with entertainment and amenities: outdoor movie theater, BBQ grill, indoor theater with 75-inch 4K TV, work desk with an ergonomic chair, and a batting cage. Relax by the fire pit with seating for 10 or cook in the modern kitchen. With 3 bedrooms, 2.5 baths, and easy access to local attractions, this is your perfect getaway. Ideal for traveling sports teams or a weekend escape. Book now for an unforgettable stay!

4.94 out of 5 average rating, 82 reviews

The kitchen area features a central wooden island with seating and ample natural light coming through multiple windows, showcasing views of the surrounding greenery. A modern refrigerator and stove are present, along with decorative elements that add character to the room.

Bungalow in Plainfield

Modern Bungalow-Near Airport/Indianapolis

Relax, escape the kids, step up your business travel, or "work from home" in this modern private bungalow with a luxurious touch. Enjoy a nice evening on the private dock or porch while listening to the crickets and bullfrogs. Have a night out at one of our favorite spots and retreat back to your quiet private oasis while you sleep in comfort on our 1000 count, 100% Egyptian cotton sheets. Conveniently located 10-15 minutes from the airport and 20-25 minutes from downtown Indianapolis.

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.

4.94 out of 5 average rating, 125 reviews

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!

A modern living room features a comfortable gray sectional sofa adorned with decorative pillows. A round coffee table is centered, and a large television is mounted on the wall. Floor-to-ceiling curtains frame a set of sliding glass doors, leading to a small balcony. A decorative plant adds a touch of greenery.

4.84 out of 5 average rating, 43 reviews

20 mins DT | Sleeps 9 | Aqua Oasis Spacious Gym

Welcome to Whitestown, IN — proudly hosted by TIBO Ventures. Standout Features: • Modern *2-BR, 2-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

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, 65 reviews

Serene 1BR: Perfect Indy Stay

Welcome to your ideal retreat in Whitestown, Indiana! Our modern 1-BR apartment is perfect for short or extended stays. Enjoy a bright living area, fully-equipped kitchen, and cozy bedroom with a queen-sized bed. Amenities include high-speed Wi-Fi, an in-unit washer and dryer, central heating and AC, free parking, a fitness center, and a pool. Conveniently located near dining, shopping, and just 20 minutes from downtown Indianapolis. Book now for a comfortable and convenient stay!

4.96 out of 5 average rating, 271 reviews

A welcoming living area features a light wood ceiling and modern furnishings. A comfortable sofa faces a round coffee table, surrounded by two leather armchairs. Natural light enters through the windows, while the adjacent kitchen area displays modern appliances and cabinetry.

Home in Speedway

Perfect 500 Location!

he perfect place to stay for all Indy events ! The whole group will enjoy easy access to everything from this centrally located place. WALK to the track! Two KING size beds! Off Street parking! Bicycles available for use for the weekends! (please request) Open layout for enjoying your travel partners. Wonderful opportunity at a great price. Close to Convention Center and all things downtown Indy too! Airport is 12 minutes away. Please, NO Cats or other type pets, beside dogs.

A spacious living area features a large green sectional sofa against a dark accent wall. Natural light floods through the sliding glass doors, which open to a balcony. A round coffee table rests on a textured area rug, complementing the modern design.

4.9 out of 5 average rating, 30 reviews

IRIE Living, Replenish Kg 2Bd+Gym+Pool, BRAND NEW!

Newly Built! Trendy 2BR Getaway Near Farmers Bank Fieldhouse | Gym, Pool & More! Make yourself at home in Whitestown, IN! This brand-new, contemporary 2-bedroom apartment is perfect for families, friends, or teams visiting Farmers Bank Fieldhouse, nearby shopping, or downtown Indianapolis, just a quick drive away. Whether you're in town for a tournament, a weekend escape, or a business trip, you'll have all the amenities you need for a relaxing and convenient stay.

A spacious bedroom is furnished with a cozy queen bed, dressed in dark blue bedding. A flat-screen TV is mounted on the wall opposite the bed. Natural light filters through large windows, illuminating the soft gray walls, while a doorway leads to an adjacent living area.

4.94 out of 5 average rating, 18 reviews

Close to All | Bright & Clean

Welcome to your first-floor luxury retreat in Whitestown, IN! This modern 1BR apartment in a newly built complex blends comfort and convenience. Enjoy a cozy queen bed, extra air mattress, fast Wi-Fi, smart TV with Prime & YouTube, and a dedicated workspace. Located near top shopping and upscale dining, it's perfect for business trips, weekend escapes, or extended stays. Stylish, peaceful, and ideally situated—everything you need for a relaxing stay is right here.

Guest house in Brownsburg

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.

4.86 out of 5 average rating, 590 reviews

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).

Popular amenities for Whitestown holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Whitestown

Home in Carmel-by-the-Sea

5 out of 5 average rating, 4 reviews

Upscale 4BR Townhome – Walk to Shops & The Monon!

4.93 out of 5 average rating, 14 reviews

Family 3BR Townhome • Garage • Fully Equipped

4.91 out of 5 average rating, 55 reviews

A castle-like structure is viewed from across a tranquil body of water, reflecting its unique architectural features. The building has a combination of large windows and a distinctive round tower, surrounded by lush greenery that enhances the serene setting.

Castle in Westfield

Wizarding World Themed Castle 8 Acres!

Flat in Indianapolis

4.81 out of 5 average rating, 42 reviews

Cozysuites Spacious 2BR next to Whole Foods

A spacious living area is furnished with a sectional sofa, armchairs, and a coffee table. A flat-screen TV is positioned on a media console. The kitchen behind features modern appliances and an island with seating. Soft lighting enhances the neutral color scheme.

4.94 out of 5 average rating, 33 reviews

Relaxing Getaway | King Bed • Balcony • Work-Ready

5 out of 5 average rating, 4 reviews

Modern Cottage steps away from Downtown Whitestown

Guest house in Greenfield

An open living area features a rustic wooden staircase leading to a lofted bedroom. A kitchenette with modern appliances is positioned under the staircase. Natural light enters through several windows, highlighting the wood accents and cozy furnishings in a welcoming layout.

5 out of 5 average rating, 22 reviews

White Barn At Sugar Creek

A modern, single-story home is presented, featuring a sleek black metal roof and a white brick exterior. Framing the entrance, well-manicured bushes and colorful flowers complement the lush green lawn, while tall trees provide shade in the background.