Two pink flowers with visible stamens, surrounded by green leaves.

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
  • 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

Our top choices for Southwestern Indiana vacation homes

1. 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
9.8 out of 10, Exceptional, (15 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 ¥34,004
¥60,940 total
includes taxes & fees
Aug 19 - Aug 20
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water

2. 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, (28 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 ¥15,783
¥31,247 total
includes taxes & fees
Aug 19 - Aug 20
Spacious 1450 sf 2 BR Private Suite w/Dog Fe

3. Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
Newburgh
9.6 out of 10, Exceptional, (43 reviews)
"We have absolutely loved it here the wildlife the owners are amazing. I hope that next time we’re in town will be able to stay here again."
United States
Kristen J.
The price is ¥14,635
¥44,246 total
includes taxes & fees
Aug 24 - Aug 25
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

4. Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space

Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
Newburgh
10.0 out of 10, Exceptional, (19 reviews)
"Enjoyed the stay immensely. Very clean. Will stay again. "
United States
Mary P.
The price is ¥19,250
¥60,482 total
includes taxes & fees
Sep 8 - Sep 9
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space

5. 1520 Howard St B "HCB"

1520 Howard St B "HCB"
Evansville
10.0 out of 10, Exceptional, (2 reviews)
"Nice place to stay, except for the traffic noise all night and the next door tenants that don't leave room for everyone to park."
United States
scott c.
The price is ¥11,910
¥23,867 total
includes taxes & fees
Aug 19 - Aug 20
1520 Howard St B "HCB"

6. 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, (9 reviews)
"Thank you for the great stay. We truly appreciated the space."
United States
Larry
The price is ¥12,499
¥36,374 total
includes taxes & fees
Aug 19 - Aug 20
Modern 2BR Townhome, 1.5 Baths, Ideal for 30+ Day Stays, Workspace + Parking

7. The Cowboys Slumber' 2 Mi to Lincoln State Park

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
9.0 out of 10, Wonderful, (2 reviews)
"We had an excellent stay! Place was nice and homey, well decorated and perfectly clean! Host was on top of making sure we had everything we needed. Would definitely recommend for anyone wanting to stay close to Holiday World or Lincoln State Park!"
United States
Jennifer C.
The price is ¥15,783
¥60,708 total
includes taxes & fees
Sep 9 - Sep 10
The Cowboys Slumber' 2 Mi to Lincoln State Park

8. Green Roof Inn | Centrally Located 2BR/1BA Home

Green Roof Inn | Centrally Located 2BR/1BA Home
Evansville
8.4 out of 10, Very Good, (6 reviews)
"A lovely little bungalow that is near the Swonder Ice Rink and some amazing local restaurants and coffee shops."
United States
Steph M.
The price is ¥14,246
¥28,299 total
includes taxes & fees
Aug 20 - Aug 21
Green Roof Inn | Centrally Located 2BR/1BA Home

9. 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 ¥14,246
¥28,116 total
includes taxes & fees
Aug 23 - Aug 24
Leaning House of Haynie | Trendy 2BR/1BA Apartment

10. 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 ¥11,910
¥23,867 total
includes taxes & fees
Aug 19 - Aug 20
House of Color A / KING 1BD/1BA Apt

11. 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, (13 reviews)
"What a great place to stay. The house is very nice and the area is great. I would definitely stay again. Ryan is great communicating with during the stay. "
United States
Mark B.
The price is ¥23,754
¥83,600 total
includes taxes & fees
Aug 19 - Aug 20
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy

12. Modern, Spacious, and Clean 2 Bedroom Townhome

Modern, Spacious, and Clean 2 Bedroom Townhome
Evansville
6.0 out of 10, (1 review)
"The property worked for me and my older son, he was having sugery at the nearby hospital so we needed a place in Evansville to stay for him to recooperate. The place was clean, the neighborhood was old but safe. Howver, the property needs some TLC."
United States
Mark B.
The price is ¥14,246
¥28,116 total
includes taxes & fees
Aug 23 - Aug 24
Modern, Spacious, and Clean 2 Bedroom Townhome

13. Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!

Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
Evansville
The price is ¥11,319
¥33,000 total
includes taxes & fees
Sep 15 - Sep 16
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!

14. Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.

Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
Evanston
10.0 out of 10, Exceptional, (25 reviews)
"Awesome quiet place highly recommend!!!"
United States
Bradley D.
The price is ¥28,696
¥52,851 total
includes taxes & fees
Aug 20 - Aug 21
Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.

15. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (11 reviews)
The price is ¥49,871
¥79,584 total
includes taxes & fees
Sep 1 - Sep 2
Run Away Reindeer Retreat

16. Cozy Vintage House. Home in Fulda, Indiana

Cozy Vintage House. Home in Fulda, Indiana
Fulda
10.0 out of 10, Exceptional, (14 reviews)
"The house was wonderful! So quaint and comfortable."
United States
Samantha I.
The price is ¥37,464
¥68,385 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Vintage House. Home in Fulda, Indiana

17. 5 Miles from Holiday World sleeps 11+ —Family Escape

5 Miles from Holiday World sleeps 11+ —Family Escape
Dale
9.8 out of 10, Exceptional, (33 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is ¥50,217
¥79,633 total
includes taxes & fees
Sep 1 - Sep 2
5 Miles from Holiday World sleeps 11+ —Family Escape

18. 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
10.0 out of 10, Exceptional, (3 reviews)
"Very cozy and clean place! It was perfect for our group of five, including three teenagers, while we visited Holiday World. Shane is a wonderful host, and the thoughtful touches - like the selection of snacks - made us feel especially welcome. Communication was easy throughout our stay. I was also fascinated by the historical books displayed on the shelves - they were such a unique and memorable touch, adding to a very historic feel of the place and the town. "
United States
Svitlana T.
The price is ¥38,101
¥59,100 total
includes taxes & fees
Aug 31 - Sep 1
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World

19. The Homestead House

The Homestead House
Henderson
10.0 out of 10, Exceptional, (2 reviews)
"Great place not far from downtown Henderson. Very quiet and comfortable. Hosts very responsive!"
United States
Amanda J.
The price is ¥22,985
¥48,698 total
includes taxes & fees
Sep 16 - Sep 17
The Homestead House

20. Corner Bungalow: Newly Renovated, Spacious & Open, Central & Convenient.

Corner Bungalow: Newly Renovated, Spacious & Open, Central & Convenient.
Evansville
10.0 out of 10, Exceptional, (5 reviews)
"Great place to stay "
United States
Dartain W.
The price is ¥40,014
¥94,233 total
includes taxes & fees
Sep 8 - Sep 9
Corner Bungalow: Newly Renovated, Spacious & Open, Central & Convenient.
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.
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

Southwestern Indiana Vacation Homes information

Number of reviews
227
Accommodation
253 Vacation Homes
Lowest Price
¥23,867
Highest Price
¥94,233