Enjoy one last adventure before the official end of summer with a Labor Day weekend getaway in Indiana. Take part in lively festivals in Auburn and Plymouth, or rest and relax in the Amish Country area of Bristol. As for accommodations, book a stay at one of numerous Indiana vacation rentals for your Labor Day weekend trip. When planning your Indiana getaway, take a look at these noteworthy cities and towns.

1. Auburn

Spend your Labor Day weekend getaway in Auburn to take part in the Auburn Cord Duesenberg Festival. Ideal for the automobile fanatics in your crew, this festival features displays of classic cars, live music, scavenger hunts for the kids, and an auction for the adults. After a full-day of festival activities, kick back at the Byler Lane Winery with a glass of chardonnay, or get in some exercise on the hiking and walking trails of Eckhart Park. Delight the kids with an afternoon of roller skating at Skatin’ Station before heading back to your vacation rental for some rest and relaxation.

Find vacation rentals near Auburn

2. Madison

Celebrate the official end of summer of Labor Day in an Indiana city featuring plenty of outdoor attractions. Madison is home to Clifty Falls State Park, where you can see fossils up close in the stony bed. Get out on the river with an adventurous boat ride hosted by Rockin’ Thunder Jet Boat Rides, or soak up the history of the city when touring the Lanier Mansion or the Jeremiah Sullivan House.

Find vacation rentals near Madison

3. Santa Claus

Labor Day weekend is your last chance of the season to ride the coasters and glide down the waterslides at the Holiday World Theme Park in Santa Claus. This magical city that celebrates Christmas all year long features water adventures at the adjacent Splashin’ Safari Water Park for the kids to enjoy. Explore the river banks of Lincoln State Park, or spend an afternoon horseback riding at Santa Stables. Don’t miss out on picking up some holiday decorations at the specialty shops before dining at the Silent Night Cafe.

Find vacation rentals near Santa Claus

Find the perfect Indiana vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

4. Plymouth

Satisfy your sweet tooth with some fresh blueberries when making Plymouth your vacation destination for your weekend getaway. This city hosts the Marshall County Blueberry Festival over the Labor Day weekend that offers fun-filled family activities, such as a blueberry stomp, fireworks, and a hot air balloon launch. Take your very own balloon ride with Michiana Balloon Rides before enjoying a vigorous game of golf at the Tri-Way Golf Club. The Showland Theatre and the Tri-Way Drive-In Theatre provide you and your family with evening entertainment.

Find vacation rentals near Plymouth

5. Indianapolis

Head to the big city of Indianapolis to take in diverse attractions that range from a trip to the Indianapolis Zoo to a tour of the Indianapolis Motor Speedway Museum. The warm September temperatures make it ideal to zip line with the Go Ape Treetop Adventure Course Company or enjoy a guided bike tour with Active Indy Tours. The aspiring artists can take in the stunning masterpieces at the Indianapolis Museum of Art, while the Fountain Square Theatre hosts several theatrical and musical performances for the entire family to enjoy.

Find vacation rentals in Indianapolis

6. Valparaiso

If you love popcorn, then you’re in for a treat with a vacation rental in Valparaiso over Labor Day weekend. This Indiana city hosts the annual Popcorn Festival each year that includes popcorn-themed activities, live entertainment, food vendors, and arts and crafts booths. Explore nature and wildlife at the Taltree Arboretum and Gardens on Saturday afternoon, then take in a powerful performance at the Memorial Opera House Saturday evening. When it’s time to soak up the sun and relax, enjoy some wine on the patio of Misbeehavin’ Meads Winery.

Find vacation rentals in Valparaiso

7. Nashville

A vacation rental in Nashville gives you a chance to hike the miles of forest at the Brown County State Park and thrill the thrill seekers with a zip lining excursion hosted by Holler Hoppin’ Zip Lines. This quaint Indiana city is known as the “artist colony of the Midwest,” and with mild September temperatures, you can comfortably explore the art galleries in the downtown area and pick up a masterpiece at the Brown County Art Guild. Let the kids learn more about trains on the Nashville Express Train Tour before your weekend getaway comes to a close.

Find vacation rentals near Nashville

8. Bloomington

Bloomington is a haven for attractions, and when you book a vacation rental in this big city, you can spend Labor Day weekend biking around the city on the Hilly Hundred Tour. Fuel up for a vigorous ride on the Little 500 with breakfast at the Village Deli. When you want to get wet and wild, make a splash in Lake Monroe to celebrate the end of summer when renting gear from Paradise Rental Boats.

Find vacation rentals in Bloomington

9. French Lick

Outdoor enthusiasts flock to French Lick for access to the Hoosier National Forest. Soak up the warm September sun and the cool breezes while hiking or biking through the forest before getting in 18 holes at the Valley Links Golf Course. French Lick is also popular with the avid shoppers who head to the downtown area to patronize specialty stores such as Bear Hollow Wood Carvers and the Finders Keepers Market Place.

Find vacation rentals near French Lick

10. Bristol

Step back into time when choosing Bristol as your Labor Day weekend vacation destination. Bristol features the Bristol Renaissance Faire on Labor Day each year that includes re-enactments, activities for the kids, and food vendors. This Indiana city puts you in the heart of Amish Country, giving you a chance to tour the Bonneyville Mill or the Elkhart County Historical Museum before retreating back to your cozy vacation rental for some family time.

Find vacation rentals near Bristol


Ready to go? Check out these amazing Indiana vacation rentals on Tripping.com.