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Holiday Homes in Southwestern Indiana

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Southwestern Indiana holiday homes

A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

1. 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 €171
includes taxes & fees
7 Sept - 8 Sept
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

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

The Cowboys Slumber' 2 Mi to Lincoln State Park
Gentryville
10.0 out of 10, Exceptional, (1 review)
"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 €326
includes taxes & fees
27 Aug - 28 Aug
The Cowboys Slumber' 2 Mi to Lincoln State Park
A two-story house with a front porch, two chairs, and a stone pillar.

3. 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, (16 reviews)
"Very attentive host. Good value. This house was perfect for our group's trip to Holiday World. We're looking at staying again in the future."
United States
Patricia G.
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

4. 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 €235
includes taxes & fees
27 Aug - 28 Aug
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

5. 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 €346
includes taxes & fees
8 Sept - 9 Sept
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A dining area with a wooden table and chairs, a bookshelf with books and decorative items, and a pet bed in the corner.

6. 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 €175
includes taxes & fees
30 Aug - 31 Aug
Green Roof Inn | Centrally Located 2BR/1BA Home
A two-story house with a red door, a small porch, and a well-maintained lawn.

7. 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 €153
includes taxes & fees
30 Aug - 31 Aug
1520 Howard St B "HCB"
A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

8. 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 €445
includes taxes & fees
14 Sept - 15 Sept
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
A modern kitchen with white cabinets, a dishwasher, and a wooden countertop.

9. 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 €148
includes taxes & fees
27 Aug - 28 Aug
House of Color A / KING 1BD/1BA Apt
A teal front door with a wreath, two potted plants, and a black and white checkered doormat with "hello" written on it.

10. 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 €170
includes taxes & fees
27 Aug - 28 Aug
Leaning House of Haynie | Trendy 2BR/1BA Apartment
A bedroom with a bed, bedside tables, a bench, and a window with curtains.

11. 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.
Modern, Spacious, and Clean 2 Bedroom Townhome
A living room with a TV, sofa, coffee table, and a dining area with a chair and table.

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

Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
Evansville
The price is €168
includes taxes & fees
22 Sept - 23 Sept
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
A compact kitchen with wooden cabinets, a stainless steel refrigerator, an oven, a microwave, a sink, and a kettle. There is a dining table with chairs.

13. 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 €419
includes taxes & fees
1 Sept - 2 Sept
5 Miles from Holiday World sleeps 11+ —Family Escape
A white house with green shutters, a covered porch, and a small garden.

14. 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 €327
includes taxes & fees
30 Aug - 31 Aug
Cozy Vintage House. Home in Fulda, Indiana
A bedroom with a bunk bed, a single bed, a wooden floor, a bookshelf, and a window with curtains.

15. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (13 reviews)
The price is €419
includes taxes & fees
1 Sept - 2 Sept
Run Away Reindeer Retreat
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

16. 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, (26 reviews)
"Awesome quiet place highly recommend!!!"
United States
Bradley D.
The price is €278
includes taxes & fees
27 Aug - 28 Aug
Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
A modern kitchen with white cabinets, stainless steel appliances, and pendant lighting.

17. 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.
Corner Bungalow: Newly Renovated, Spacious & Open, Central & Convenient.
A single-story house with a gabled roof, white shutters, and a front porch.

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 €316
includes taxes & fees
7 Sept - 8 Sept
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
A modern kitchen with a central island, built-in appliances, and a dining area with a window.

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 €262
includes taxes & fees
24 Sept - 25 Sept
The Homestead House
A spacious living room with a fireplace, a large window, and a high ceiling with exposed beams.

20. Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (11 reviews)
"Very beautiful and comfortable house for our stay"
United States
James S.
Family Friendly Lakehouse with great views!
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.
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Top Southwestern Indiana Hotel Reviews

Baymont by Wyndham Dale

Baymont by Wyndham Dale

10/10 Excellent
"It was a very comfortable stay"
Jami 2-night trip
Posted 6 hours ago
Baymont by Wyndham Dale

Find out more about Southwestern Indiana

Southwestern Indiana Holiday Homes information

Number of reviews
243
Accommodation
128 Holiday Homes
Lowest Price
€148
Highest Price
€445