Family-friendly holiday rentals in Boone County

Crossroads: Endless entertainment in Lebanon

Stay in a huge, fully remodeled historic home with something to keep everyone happy- golfing, karaoke, 6 arcade games, a Playstation, board games, TVs with ESPN, a pool table, toys & a bar. Cook to your heart's content in our fully stocked kitchen, inc. a Crockpot, coffee bar, blender, 5 types of grills/smokers (outside of course). This is in walking distance to downtown Lebanon and sleeps 12 across 4 bedrooms (plus 3 full bathrooms). There are multiple seating areas and outdoor areas to enjoy.

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

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.

Pet-Friendly Acreage Short Drive to Grand Park

Pet-friendly acreage retreat in rural Zionsville near Grand Park. Serene views, cozy firepit, and fast 1 Gbps Wi-Fi. Ideal for families and tournament parents. Sleeps 5 • 3 beds (2 queen, 1 twin) + inflatable mattress if needed (full) • 1.5 baths. Light-filled living/dining, practical kitchen, workspace-friendly table. Open yard (not fenced); supervise pets. Quick drive to Zionsville, Carmel, Westfield; on-site parking. No parties, quiet hours, no smoking. Book early for Grand Park weekends.

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!

The Hornaday House

Charming Family Retreat in Lebanon, IN – 5 Bedrooms, 2 Bathrooms Welcome to your spacious 5-bedroom, 2-bathroom home, perfect for families or groups! Enjoy large living area, fully equipped kitchen, and outdoor space. Walking distance from downtown Lebanon and Memorial Park. Easy access to I-65, Farmers Bank Fieldhouse, and Grand Park Sports Complex. Within 35 minutes from Indianapolis and Lafayette. Book your stay today for a comfortable and memorable getaway!

North Meridian • Est. 1913

This lovingly preserved 1913 historic home blends timeless character with modern comfort. Enjoy peaceful views, morning coffee on the covered front porch, and the convenience of being just a short walk to downtown Lebanon’s shops and restaurants. Located steps away from Lebanon Memorial Park. Centrally located between Westfield, Lafayette, and Indianapolis, it’s an ideal home base for work, events, or a relaxing getaway. Please note: Stairs are required to enter.

Close to Indy - Sleeps 14, Poker Room, Coffee Bar

Welcome to our beautiful vintage home in Lebanon, IN! Built in the early 1900s and recently remodeled, this spacious 3-level house sleeps 14 and features 4 large bedrooms, 2.5 baths, a fully stocked kitchen with a coffee bar, and even a poker room! Just a 3-minute walk to Lebanon’s town square and a 30-minute drive to downtown Indy, it's perfect for families, larger groups, or wedding guests seeking comfort, charm, and convenience.

Stylish Stay | Near Everything!

Welcome to your perfect getaway! This stylish 2-bed, 2-bath unit features a king-size bed, smart TV, and private bathroom in the master suite, plus a cozy queen bed in the second room. Enjoy a second full bathroom, smart TV in the living room, a private balcony with lovely views, fully stocked kitchen, in-unit laundry, and a warm, inviting living space. Ideal for short- or long-term stays—comfort and convenience await!

A better alternative than a hotel room

Relax in this private stylish space. Long-term rental possible. Located in a quiet neighborhood walking distance to local restaurants, brewery, convenience store and walking trail. Well appointed kitchenette includes stove top, microwave, air fryer and everything you need to prepare your homemade meals. Enjoy the backyard porch with access to a fire pit and gas grill. Parking is steps away from your private entrance.

Florence Cottage~Modern Country

Relax and unwind at Florence Cottage, a peaceful retreat in quiet Whitestown that blends country charm with modern style. Set on an acre with mature trees, enjoy sunrise from the front porch and sunsets from the back deck. The home features 4 bedrooms and 2 full baths, including a spacious primary suite, queen bedrooms, and a bunk room—perfect for families or group getaways.

Suite 39 North

Centrally located in Lebanon, with great access to the Lebanon Business park, Lilly site, and vibrant downtown. This suite will satisfy the business traveler on the go. 2 Bedrooms, 1 Bath, full size eat in kitchen, Roku TVS, dedicated work space with a HP color Laser printer. Enjoy your stay at Suite 39 North.