Family-friendly holiday rentals in Lebanon

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.

KitchenIndoor spacesLong stay

5.0 out of 5 average rating, 16 reviews

Home in Lebanon

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.

FamilyIndoor spacesSleep quality

Superhost

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, 122 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.

KitchenIndoor spacesCondition

4.97 out of 5 average rating, 212 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.

KitchenIndoor spacesHiking

4.91 out of 5 average rating, 128 reviews

The front exterior of the house features a welcoming entrance with a bright green door framed by two windows. Flanking the door are two black patio chairs situated on a stone pathway, leading to a fenced yard adorned with white gravel and decorative plants.

Home in Sheridan

Doll House

Small (530 sqft) private house in Sheridan, IN. Quaint small town privacy. No cleaning fee if complying with house rules. Easy access to US 31 and US 421. Convenient to Grand Park , Ruoff, Monon Trail (walk, bike, run), Westfield, Carmel, Noblesville, Fishers and surrounding areas; 30 minutes to Ruoff Music Center; 15 minutes to Grand Park. NO parking behind the house only in front of house or across the street. Pets with prior approval only. Please be accurate with #people, pets.

FamilyIndoor spacesCheck-in

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, 175 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 spacesCheckout

5.0 out of 5 average rating, 38 reviews

A charming two-story home is set in a landscaped yard, featuring steps leading to the entrance. Flower pots with greenery and colorful blooms provide visual interest, while an American flag stands prominently at the front. Large windows reflect natural light in the late afternoon.

Home in Lebanon

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!

Indoor spacesKitchenQuiet

4.94 out of 5 average rating, 268 reviews

A charming exterior of the lodge is featured, showcasing a wooden porch supported by exposed beams. A wedding dress is displayed on a hanger, highlighted against the rustic backdrop. Lush green plants and a decorative bench add to the inviting atmosphere.

Cabin in Crawfordsville

Townsend Lodge at Hidden Hollow Farm

The lodge is a very private/secluded setting located on 62 wooded acres. Everything nature has to offer is just outside the door. Enjoy the trails, garden ponds, or just relax on the porch and listen to the birds sing all day long. Inside you will find all the comforts of home along with fireplace, cabin decor, and walk-in shower with unlimited hot water. Perfect place for a couples romantic getaway or gatherings for holidays, bachelorette/bachelor party, and more.

Indoor spacesKitchenLaundry

4.87 out of 5 average rating, 629 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).

KitchenIndoor spacesView

A welcoming entry area is highlighted by a chalkboard sign displaying the word 'Welcome.' Sunflowers in a glass vase add a touch of color. The open layout reveals a spacious living room and dining area, featuring a large TV, comfortable seating, and a round table.

4.91 out of 5 average rating, 180 reviews

Grand Park HUGE Space Sleeps 13+|Tons of Parking

Spacious 2400+ sq ft farmhouse retreat, perfect for teams and large groups! This beautifully updated home sleeps 13+ with 12 beds and is just 10 minutes from Grand Park. Enjoy a wide-open layout, large deck, and private yard with plenty of space to relax. No street parking—room for 6+ SUVs. Stay connected with fast WiFi, Xbox, and streaming. Minutes from downtown Westfield, Carmel, and Zionsville—ideal for tournaments, family trips, or group getaways.

Indoor spacesKitchenParking

4.89 out of 5 average rating, 35 reviews

The vintage house features a spacious front porch with multiple entry points, surrounded by neatly trimmed bushes and a well-maintained lawn. Large windows allow natural light to brighten the exterior, while nearby trees provide shade and a pleasant atmosphere.

Home in Lebanon

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.

FamilyIndoor spacesCondition