The Best Vacation Rentals to Book in Indiana

Get a feel for real Midwest life with a stay at one of the best Indiana vacation rentals
Get a feel for real Midwest life with a stay at one of the best Indiana vacation rentals | © Patricia E. Thomas / Alamy Stock Photo
Sarah Warwick

Known as the Crossroads of America, Indiana is a jewel of the Midwest. Tourists come to enjoy the beaches of Lake Michigan and to explore the urban delights (and crazy motor racing) of Indianapolis along with the state’s gorgeous expanses of rolling farmland and cornfields. Heading to the Hoosier State? If you’re interested in seeing what real Midwest life is like, opt for one of the best Indiana vacation rentals. From cottages to mansions, these dreamy vacay stays can be booked right now via Culture Trip.

Lake Michigan Beach Cottages, for lakeside relaxation


Adirondack chairs and a hammock at Lake Michigan Beach Cottages close to the beach
Courtesy of Lake Michigan Beach Cottages / Expedia

This charming cottage is just a few minutes’ walk from Sheridan Beach, and a short drive from enjoyable sites such as Indiana Dunes National Park, Washington Park Zoo and the Friendship Botanic Gardens. Softly decorated throughout, the 14-sleeper property features five bedrooms (including a bunk bed) and three bathrooms, so bring along family and friends. The fully equipped kitchen, sun deck and beachside hammock are everything you could need for a relaxed Indiana beach vacation. You may never want to leave.

Speedway Charm, for pole position during the Indy 500


A modern living space with an L-shaped couch at Speedway Charm
Courtesy of Speedway Charm / Expedia

If you’re one of the more than 250,000 people who descend on Indianapolis for the Indy 500 each year, then you’ll want to book this spotlessly clean and compact bungalow. It’s within easy walking distance to the Speedway, where the iconic race and many others are held, as well as a museum that charts the city’s passionate relationship with motor racing. Owners Brett and Kim are considerate hosts, too.

Sanitized Newly Designed Super Chic Indy Home Near Fountain Square, for a home away from home


This Indianapolis home might look a bit small from the outside, like some kind of quaint Scandi structure, but when you walk in – wow. It opens up to reveal a chic home away from home, featuring luxe furnishings, modern lighting and a brand new kitchen, complete with marble surfaces and a giant fridge. The sociable, open-plan living area has a cozy corner sofa and a flatscreen TV. There’s a deck with a barbecue out back, plus a games room with foosball and pool tables tucked away in the garage.

Designer 5BR House Steps to Downtown/Fountain Square, for central glamour


Designer living space with wood floors with stairs to upper floor
Courtesy of Designer House 5BR Steps to Downtown/Fountain Square / Expedia

From its red-brick exterior and picture-perfect porch to its cheerily decorated interiors, complete with striped armchairs, this Indianapolis house is simply gorgeous. On the first floor, large windows flood the living area with light, and on hot summer evenings you can dine out on the garden patio. Upstairs, you’ll find five bedrooms and two bathrooms – there’s even a freestanding bath for that touch of glamour. As the name suggests, you’ll be walking distance from Fountain Square, so it’s close to the city’s main sights, but far enough away from the action to ensure a good night’s sleep.

Pleasant Grove Farm LLC, for a rural retreat


View of a cottage at Pleasant Grove Farm on a grassy spot in front of a pond
Courtesy of Pleasant Grove Farm LLC / Expedia

Indiana is famous for its farmland, and you can experience the best of its rural charm with a stay at one of this farm’s wooden cottages. Choose from four rustic accommodations, sleeping from two to six, complete with barbecues and picnic areas as well as self-catering facilities inside. Sitting on 50 acres (20ha) in Greene County, around two hours southwest of Indianapolis, this is the perfect vacation spot for keen anglers, hikers, bikers and birdwatchers, as well as those who want to experience silent nights and starry unpolluted skies.

Blue Door Cottages, for water sports on Lake Shafer


The gated pool area with lounge chairs at Blue Door Cottages
Courtesy of Blue Door Cottages / Expedia

Located halfway between Indianapolis and Chicago, Lake Shafer is a sleepy reservoir, created for pleasure cruises in the 1920s. Today, it’s home to the tourist center of Monticello, the Indiana Beach amusement resort and these compact, colorful chalets. Within the accommodation complex, there’s an outdoor pool, barbecue grills and a picnic area plus free wifi and parking; and you’re just one minute from the lake for fishing, boating and water sports galore.

Spacious 3BR Ranch House W/patio Yard in a Quiet Suburb, for a Louisville detour


Exterior view of ranch house in a quiet suburb
Courtesy of Spacious 3-BR Ranch House With Patio Yard in a Quiet Suburb / Expedia

If you’re traveling around Indiana, you may want to take a detour to Louisville, Kentucky – home of Muhammad Ali, Kentucky Fried Chicken and the world-famous Derby. Although the city itself is just over the state line, the city’s northern suburbs are technically in Indiana, and Sellersburg is home to this cute ranch house that sleeps 10 folks. It’s particularly good for families, with memory foam mattresses, plus a big yard and outdoor/indoor dining tables. As well as Louisville itself (a 20-minute drive), you can explore Clark State Forest, Deam Lake and fruit-picking farms nearby.

3BR Walkout Basement Apartment, for a historical outing


Large living room with red and burgundy leather sofas and wood floors
Courtesy of 3BR Walkout Basement Apartment / Expedia

New Albany is technically another Louisville suburb, but it wasn’t always in Kentucky. New Albany was actually the largest city in Indiana from 1816 until 1860, so it has a rich hoosier history of its own, such as at the Town Clock Church, a stop on the Underground Railroad. Stop for souvenirs at the Odd Shop, grab freakshakes at Boomtown Creamery and enjoy free summer concerts at the Riverfront Amphitheater. This rental is a chilled-out base for exploring the area’s cultural offerings, and you’ll feel like an old-timey person in the luxurious living room armchair.

culture trip left arrow
 culture trip brand logo

Volcanic Iceland Epic Trip

meet our Local Insider


women sitting on iceberg


2 years.


It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.


I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!

culture trip logo letter c
group posing for picture on iceberg
group posing for picture on iceberg

Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.

map of volcanic iceland trip destination points
culture trip brand logo
culture trip right arrow
landscape with balloons floating in the air


Connect with like-minded people on our premium trips curated by local insiders and with care for the world

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.


Holiday Sale Offers on Our Trips

Incredible Savings

Edit article