Search Vacation Homes in Southwestern Indiana

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Southwestern Indiana vacation homes

Interior

Spacious 1450 sf 2 BR Private Suite w/Dog Fe

Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Huntingburg
9.8 out of 10, Exceptional, (22 reviews)
"Great place to stay for a few days if you're visiting Holiday World or the area. "
United States
Brandon S.
The price is AED 404
AED 761 total
includes taxes & fees
30 Jun - 1 Jul
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
Smart TV, books

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.8 out of 10, Exceptional, (37 reviews)
"Great stay!"
United States
Kristi M.
The price is AED 337
AED 1,019 total
includes taxes & fees
1 Jun - 2 Jun
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Fridge, microwave, oven, stovetop

Barn in the Burgh | Event Space | Sleeps 12

Barn in the Burgh | Event Space | Sleeps 12
Newburgh
10.0 out of 10, Exceptional, (15 reviews)
"Enjoyed the stay immensely. Very clean. Will stay again. "
United States
Mary P.
Barn in the Burgh | Event Space | Sleeps 12
Interior

Modern 2BR Townhome, 1.5 Baths, Ideal for 30+ Day Stays, Workspace + Parking

Modern 2BR Townhome, 1.5 Baths, Ideal for 30+ Day Stays, Workspace + Parking
Evansville
9.4 out of 10, Exceptional, (6 reviews)
"Thank you for the great stay. We truly appreciated the space."
United States
Larry
The price is AED 297
AED 743 total
includes taxes & fees
2 Jun - 3 Jun
Modern 2BR Townhome, 1.5 Baths, Ideal for 30+ Day Stays, Workspace + Parking
Interior

House of Color A / KING 1BD/1BA Apt

House of Color A / KING 1BD/1BA Apt
Evansville
9.4 out of 10, Exceptional, (3 reviews)
"The spsce was really well presented and very clean. "
United States
Ronald G.
The price is AED 285
AED 632 total
includes taxes & fees
2 Jun - 3 Jun
House of Color A / KING 1BD/1BA Apt
3 bedrooms, desk, WiFi

The Chic Shack | Centrally Located 2BR/1BA Home

The Chic Shack | Centrally Located 2BR/1BA Home
Evansville
10.0 out of 10, Exceptional, (2 reviews)
"It felt like home in this space. All the extra throw blankets to be warm and cozy. The host is very easy to work with."
United States
Meisha W.
The price is AED 376
AED 804 total
includes taxes & fees
1 Jun - 2 Jun
The Chic Shack | Centrally Located 2BR/1BA Home
Exterior

Cozy Vintage House. Home in Fulda, Indiana

Cozy Vintage House. Home in Fulda, Indiana
Fulda
9.8 out of 10, Exceptional, (9 reviews)
"The house was wonderful! So quaint and comfortable."
United States
Samantha I.
The price is AED 874
AED 1,588 total
includes taxes & fees
1 Jun - 2 Jun
Cozy Vintage House. Home in Fulda, Indiana
Exterior

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Lynnville
10.0 out of 10, Exceptional, (9 reviews)
"Cute quiet lil house located around attractions for families. Well worth the money and host is always available "
United States
Madison B.
The price is AED 526
AED 1,070 total
includes taxes & fees
8 Jun - 9 Jun
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
Fridge, microwave, oven, stovetop

Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy

Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
Evansville
10.0 out of 10, Exceptional, (5 reviews)
"Every detail was perfect for our whole family. We couldn’t have been more comfortable. "
United States
Katie C.
The price is AED 731
AED 2,167 total
includes taxes & fees
14 Jun - 15 Jun
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
Exterior detail

Leaning House of Haynie | Trendy 2BR/1BA Apartment

Leaning House of Haynie | Trendy 2BR/1BA Apartment
Evansville
9.0 out of 10, Wonderful, (4 reviews)
"Perfect location with comfortable beds. The kitchen is minimal - good for eating a simple breakfast."
United States
Kathryn H.
The price is AED 344
AED 788 total
includes taxes & fees
1 Jun - 2 Jun
Leaning House of Haynie | Trendy 2BR/1BA Apartment
Interior

3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World

3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Ferdinand
The price is AED 922
AED 1,416 total
includes taxes & fees
1 Jun - 2 Jun
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
Fridge, microwave, oven, stovetop

Mid-Century Brick Bungalow Home

Mid-Century Brick Bungalow Home
Evansville
6.8 out of 10, (26 reviews)
"This was such a cute overnight stay! I loved the decor, and it was perfect for us!"
United States
Chelsea M.
The price is AED 350
AED 847 total
includes taxes & fees
1 Jun - 2 Jun
Mid-Century Brick Bungalow Home
Fridge, microwave, oven, stovetop

5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.6 out of 10, Exceptional, (18 reviews)
"Such a cute and cozy place that had everything we needed! Beds were all super comfy, and with 3 little ones with us, the game room was fantastic. Would definitely recommend!!!"
United States
Lauren M.
The price is AED 1,157
AED 1,835 total
includes taxes & fees
4 Jun - 5 Jun
5 Miles from Holiday World sleeps 11+ —Family Escape
Smart TV

Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (5 reviews)
The price is AED 992
AED 1,263 total
includes taxes & fees
2 Jun - 3 Jun
Family Friendly Lakehouse with great views!
Interior

Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path

Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path
Lewisport
10.0 out of 10, Exceptional, (1 review)
"What a great place to stay to get away from it all with the family! "
United States
Favour R.
The price is AED 797
AED 1,211 total
includes taxes & fees
29 Jun - 30 Jun
Ultimate private 4 bedroom 3 full bathrooms right next to golf course with path
Property grounds

The Family Oasis just 6 miles from Holiday World

The Family Oasis just 6 miles from Holiday World
Gentryville
9.2 out of 10, Wonderful, (45 reviews)
"Great location to Holiday World’s "
United States
Gary S.
The price is AED 1,017
AED 1,653 total
includes taxes & fees
11 Jun - 12 Jun
The Family Oasis just 6 miles from Holiday World
Living area

Harrison Place - Located on Evansville's Eastside

Harrison Place - Located on Evansville's Eastside
Evansville
The price is AED 1,084
AED 1,977 total
includes taxes & fees
7 Jun - 8 Jun
Harrison Place - Located on Evansville's Eastside
Interior

Explore the Shawnee National Forest-reserve the SHAWNEE HIDEAWAY

Explore the Shawnee National Forest-reserve the SHAWNEE HIDEAWAY
Equality
9.6 out of 10, Exceptional, (20 reviews)
"great host. great place to stay will definitely be coming back, ty"
United States
Anonymous traveler
The price is AED 478
AED 798 total
includes taxes & fees
2 Jun - 3 Jun
Explore the Shawnee National Forest-reserve the SHAWNEE HIDEAWAY
Fridge, microwave, oven, stovetop

Dome View Renovated Bungalow

Dome View Renovated Bungalow
West Baden Springs
10.0 out of 10, Exceptional, (22 reviews)
"Clean& comfortable , close to spa destination "
United States
Eileen S.
The price is AED 268
AED 685 total
includes taxes & fees
4 Jun - 5 Jun
Dome View Renovated Bungalow
Terrace/patio

Bluegrass Bungalow 2 bedrooms with large porch

Bluegrass Bungalow 2 bedrooms with large porch
Owensboro
9.8 out of 10, Exceptional, (37 reviews)
"Second time we stayed at the bungalow - worked out perfect for basketball tournament - close to Sports Center and restaurants! Would definitely recommend and stay again!"
United States
Susan S.
The price is AED 375
AED 679 total
includes taxes & fees
8 Jun - 9 Jun
Bluegrass Bungalow 2 bedrooms with large porch
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwestern Indiana Hotel Reviews

Comfort Inn Ferdinand

Comfort Inn Ferdinand

10/10 Excellent
"I had an employee and her family stay after work. Her family enjoyed the pool and breakfast"
Stephanie 1-night trip
Posted 2 hours ago
Comfort Inn Ferdinand

Explore a world of travel with Expedia