Photo by Steve Ignowski

Southwestern Indiana Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Southwestern Indiana

Cabin in Tennyson

9.6 out of 10, Exceptional, (60)
"We enjoyed the property and Doug was a welcoming host. "
United States
Bess C.
The price is AU$245
includes taxes & fees
1 Dec - 2 Dec
Guest House with acreage to explore.

Cabin in Dale

9.6 out of 10, Exceptional, (20)
"Very nice cabin very clean overall really enjoyed"
United States
Addy D.
The price is AU$367
includes taxes & fees
1 Dec - 2 Dec
Yellow Banks Log Cabin With Waterfront Views

Holiday Home in Evansville

9.6 out of 10, Exceptional, (68)
"Great week in a great neighborhood "
United States
BRENDA B.
Something to talk about in Haynie's Corner! Walk anywhere, sleeps 6!

Cabin in Dale

10.0 out of 10, Exceptional, (17)
"Great setting, good beds, and clean!"
United States
Doug W.
The price is AU$367
includes taxes & fees
1 Dec - 2 Dec
Yellow Banks Log Cabin With Waterfront Views

Holiday Home in Huntingburg

9.8 out of 10, Exceptional, (20)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
The price is AU$302
includes taxes & fees
7 Dec - 8 Dec
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Holiday Home in Evansville

The price is AU$640
includes taxes & fees
1 Dec - 2 Dec
Fall Bliss: Charming 3BR Home with Sauna & Hot Tub

Holiday Home in Dale

9.2 out of 10, Wonderful, (12)
"This property is amazing! We loved the privacy and peacefulness. The house is great and we will definitely be coming back!"
United States
Natalie S.
The price is AU$411
includes taxes & fees
5 Dec - 6 Dec
Tranquil Hideaway: Your Private Lakefront Retreat

Holiday Home in Newburgh

9.8 out of 10, Exceptional, (34)
"Enjoyed staying in this cozy little spot and admiring the history within its walls. Would definitely consider staying here again!"
United States
Rachel G.
The price is AU$440
includes taxes & fees
1 Dec - 2 Dec
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Holiday Home in Dale

9.4 out of 10, Exceptional, (12)
"Absolutely amazing host, they made the check in process so easy. It was minutes from Holiday World so it made our trip so well worth it. The house was beautiful and the game room was the favorite part of the kid’s night. "
United States
Sabrina S.
The price is AU$593
includes taxes & fees
1 Dec - 2 Dec
5 Miles from Holiday World sleeps 11+ —Family Escape

Holiday Home in Evansville

10.0 out of 10, Exceptional, (5)
"The property is so beautiful the house is amazing. The rooms were so beautiful. The kids loved the pool. The hot tub was so relaxing. We enjoyed making s’mores it was truly amazing and relaxing experience "
United States
Jillian J.
Country Homeplace 4-bedroom Pool-HotTub pets ok Near Toyota

Holiday Home in Evansville

9.0 out of 10, Wonderful, (19)
"Everything went well"
United States
Calvin M.
Haynie's Charmer - 3 BR NEW CONSTRUCTION Modern!

Holiday Home in Evansville

9.8 out of 10, Exceptional, (76)
"Perfect location for our stay. House had everything we needed. Definitely would stay here again next time we’re in Evansville."
United States
John J.
Cozy Bungalow in a nice friendly neighborhood

Holiday Home in Evansville

10.0 out of 10, Exceptional, (16)
"The cottage was the perfect place for us to stay and visit with our daughter. Kathleen was very quick to return any messages or phone calls for all of our needs. We will definitely be using this property again!"
United States
Tracy B.
Cozy Cottage, 3 mins from EVV, fenced yard

Apartment in Downtown Evansville

9.0 out of 10, Wonderful, (8)
"Had a wonderful few days at the Harrison place. Would stay again. "
United States
Brittany B.
The price is AU$267
includes taxes & fees
6 Dec - 7 Dec
The Harrison A / 1BD/1BA Apt steps from Riverfront

Holiday Home in Evansville

9.8 out of 10, Exceptional, (17)
"Great house. Fun game room, all updated and clean interiors."
United States
Scott J.
Oakside Retreat – Private Getaway with Huge Yard, Firepit and Game Room

Cabin in Fulda

10.0 out of 10, Exceptional, (101)
"Great location close to Holiday World. Home had everything you need. Very well equipped and comfortable for our family of 14. Emily was great to work with. Thank you!!"
United States
Barb P.
5-bedroom cabin just 14 minutes from Holiday World and Splashin' Safari

Apartment in Evansville

The price is AU$456
includes taxes & fees
1 Dec - 2 Dec
"Downontheabby" Two bed One bath with great wifi and fun attractions!

Aparthotel in Evansville

10.0 out of 10, Exceptional, (1)
The price is AU$449
includes taxes & fees
13 Dec - 14 Dec
New Boutique Hotel Suite on Haynie's Corner: KING Bed, Parking, Security & More!

Cabin in Wadesville

10.0 out of 10, Exceptional, (2)
"We really enjoyed staying in this wonderfully restored cabin. It's private, tastefully decorated and beautifully landscaped. We'll definitely stay again if we're in the area. Highly recommend!"
United States
ANNABELLE M.
Charming 2-bedroom cabin in enchanting Wadesville with Heat, AC, WiFi, Hot Tub

Holiday Home in Evansville

Serene bungalow with AC, Bathtub & Modern Amenities in Evansville
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Black Friday Sale

Save up to 40% on select hotels
Save an average of 15% on thousands of hotels when you're signed in

Top Southwestern Indiana Hotel Reviews

Find out more about Southwestern Indiana

Everything you need to know about Southwestern Indiana holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Southwestern Indiana holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwestern Indiana holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Southwestern Indiana holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwestern Indiana. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwestern Indiana holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwestern Indiana holiday rentals we have selected for you start as low as AU$245 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Southwestern Indiana rentals

At Expedia, we put the best Southwestern Indiana holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Southwestern Indiana rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwestern Indiana holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwestern Indiana. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.