Family-friendly vacation rentals in Whitestown

A two-story home features a combination of brick and siding, complemented by neatly trimmed shrubs and trees. The attached two-car garage is visible, showcasing a paved driveway. Large windows provide ample natural light, enhancing the inviting appearance of the front entrance.

4.99 out of 5 average rating, 107 reviews

Grand Park minutes away Sleep 13, 11 beds

Tournament at Grand Park with the team or plans to enjoy downtown Westfield, Carmel or Indy? This house has you covered with plenty of fun and games for the whole family and easy access to shopping and restaurants. This home is in a quiet neighborhood with nearby access to the Midland Trace Trail and the Monon Trail. The fully fenced in backyard is a great space for the family or enjoy playing the Nintendo switch and a few rounds of foosball. The backyard includes patio, grill, seating and more.

Indoor spacesFamilyAmenities

4.9 out of 5 average rating, 50 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

Indoor spacesFamilyLong stay

4.84 out of 5 average rating, 133 reviews

The front view of the house showcases a classic white exterior with a welcoming entrance. Lush green shrubs frame the entrance, and a driveway leads to a detached garage seen in the distance. A clear blue sky complements the home's inviting appearance.

Home in Brownsburg

Cozy and Comfortable, great Fall destination!

This house is an old model, but it is a cozy comfortable house and will everything you need for your stay. In Brownsburg it's only minutes from the Indianapolis Raceway Park and the Lucas Oil Raceway. There is plenty of entertainment and food options within driving distance and a couple you can walk to. I have wifi and streaming with a Fire Stick available on the TV. I do not have cable. I have Netflix, Disney, HBO. Feel free to bring your own Streaming Devices to access your own shows.

Indoor spacesKitchenCondition

Superhost

A welcoming living area features stylish black seating with gold accents, complemented by a modern coffee table. A large television displays a serene autumn scene. Natural light filters through the balcony doors, illuminating a decorative indoor plant and soft textiles arranged in the space.

Apartment in Whitestown

4.83 out of 5 average rating, 30 reviews

20 mins DT | Illustrious Suite Spacious ExtraBeds

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 ✔ Pool

Indoor spacesKitchenAmenities

A modern kitchen is featured with dark cabinetry and a spacious island. Stainless steel appliances are positioned for convenience. Natural light fills the area, highlighting the marble countertops. A cozy seating area can be seen in the background, creating a welcoming space for family gatherings.

4.98 out of 5 average rating, 126 reviews

Rolling Hill Retreat @ GrandPark

Relax with the entire family at this completely renovated, peaceful retreat in Westfield. This 3 bedroom/2 bath ranch is conveniently located 8 minutes from Grand Park. The home accommodates up to 10 people comfortably. The fully stocked kitchen is the heart of the home with new appliances and breakfast bar seating. Both baths have double sinks to make getting ready a breeze. Enjoy the private backyard space with a tranquil creek or walk to the nearby Monon Trail with over 25 miles of trails.

Indoor spacesFamilyCondition

4.97 out of 5 average rating, 214 reviews

A charming cottage exterior is framed by a blossoming tree in the foreground. The wooden deck features a railing and is accessible through a glass-paneled door. Nearby, lush green grass extends toward an open field in the background, suggesting a serene rural setting.

Farm stay in Thorntown

Heavenly Acres Farm and Learning Center

Experience a relaxing stay, spending time watching chickens happily foraging or barn animals as they graze in the pasture. Take a walk by the creek, taking in the country sunset.Enhance your experience by interacting with the animals during a farm tour or helping with daily chores. We also offer a variety of learning opportunities as we share how we process fiber, health care for animals or maybe a simple hay ride. Here at Heavenly Acres we want to provide you with a unique farm experience.

FamilyKitchenWalkability

5.0 out of 5 average rating, 24 reviews

Home in Whitestown

Modern Cottage steps away from Downtown Whitestown

Enjoy a trendy stay in downtown Whitestown! Our comfortable & cozy house will be your home away from home - fully equipped kitchen surrounded by modern furnishings - 3BR - 1 king/2 queens. Cross the road for a delicious brew and breakfast at Hattie’s Coffeehouse or take a short walk to Moontown Brewery for the game. Pick up Greeks pizza or sit down and dine at LA Cafe- all steps away! Big 4 bike trail access is close by as well! Or catch the fun in downtown Indy just 30 minutes away!

Indoor spacesKitchenBiking

A charming brick home is pictured with a well-maintained lawn featuring green grass and landscaped flower beds. A wide pathway leads to the front porch, which is adorned with potted plants. Nearby trees and blooming flowers provide a vibrant, inviting touch.

4.99 out of 5 average rating, 177 reviews

The Penn House 3 miles to Grand Park Sleeps 14

The Penn House is a luxury home in the heart of Westfield perfect for the discerning traveler! All the comforts of home nestled in downtown Westfield. Walking distance to shops, restaurants, parks, the Monon Trail, and a quick five minute drive to Grand Park Sports Campus. Feel at home with an inviting front porch, large backyard with a gas grill, and fire pit for some outdoor fun. House is a few blocks from sushi, pizza, Italian, a brewery and wine bar. Perfect Location!

FamilyIndoor spacesComfort

5.0 out of 5 average rating, 14 reviews

Home in Whitestown

Trailside Getaway | Luxury Space| Sleeps 10+

Bring the whole family to this great home with lots of room for fun! Contractors welcome! Close to the LEAP District and Grand Park if you're in town for a tournament. Tons of stores, shopping, and restaurants nearby! Looking to get away to a comfortable home? Look no further. This fully stocked townhome is great for your short trip or even for a longer stay if you prefer! Beautiful views of the lake and serene countryside. Brand new and extremely clean! Your stay awaits!

Indoor spacesFamilyCondition

4.87 out of 5 average rating, 635 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).

Indoor spacesKitchenBiking

Superhost

An open kitchen and dining area are showcased, featuring a large wooden dining table with black chairs and a modern light fixture above. Stainless steel appliances line the kitchen counters, and a cozy seating area with leather sofas is visible through the sliding glass door.

4.87 out of 5 average rating, 175 reviews

Private/spacious home w/backyard near Grand Park

Beautifully renovated spacious Westfield charmer with massive private backyard. Minutes from GrandPark, Downtown Carmel/Westfield, as well as Monon Trail. Updated kitchen opens into living/dining areas to allow for family gathering or entertaining easily. Gorgeous walkout basement is perfect for backyard fun and games. Enjoy your morning coffee on the relaxing front porch. Perfect for multi families traveling together or guests wanting privacy and convenience.

Indoor spacesKitchenComfort