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Holiday Homes in Southwestern Indiana

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Southwestern Indiana holiday homes

A two-story house with a front porch, two chairs, and a stone pillar.

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, (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 price is AU$409
includes taxes & fees
6 Oct - 7 Oct
THE GETAWAY-Charming 3 Bdrm 2 Bath, Sleeps 8-10 Lg Drive, WiFi, Tankless Water
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

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, (29 reviews)
"Me and my family stayed while visiting holiday world and we highly recommend. Prices was affordable and the host was great."
United States
James B.
The price is AU$282
includes taxes & fees
30 Sept - 1 Oct
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A modern living room with a sectional sofa, a coffee table, and decorative plants.

3. Trendy Two bedroom home centrally located near UE

Trendy Two bedroom home centrally located near UE
Evansville
9.0 out of 10, Wonderful, (11 reviews)
"Would stay again"
United States
Scott D.
The price is AU$278
includes taxes & fees
4 Oct - 5 Oct
Trendy Two bedroom home centrally located near UE
A wooden interior with a leather sofa, a wooden coffee table, and a kitchen area visible through an open door.

4. 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 AU$560
includes taxes & fees
30 Sept - 1 Oct
The Cowboys Slumber' 2 Mi to Lincoln State Park
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, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is AU$579
includes taxes & fees
30 Sept - 1 Oct
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

6. 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, (44 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 AU$393
includes taxes & fees
8 Oct - 9 Oct
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
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 AU$236
includes taxes & fees
4 Oct - 5 Oct
1520 Howard St B "HCB"
A dining area with a wooden table and chairs, a bookshelf with books and decorative items, and a pet bed in the corner.

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 AU$294
includes taxes & fees
4 Oct - 5 Oct
Green Roof Inn | Centrally Located 2BR/1BA Home
A modern hotel room with a large flat-screen TV, a dining area with a chandelier, and a cozy seating arrangement.

9. 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 AU$308
includes taxes & fees
4 Oct - 5 Oct
The Chic Shack | Centrally Located 2BR/1BA Home
A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

10. 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)
"Property was as advertised - Ryan was excellent to work with. I wouldn’t hesitate to stay at this property again!"
United States
Jacob O.
The price is AU$775
includes taxes & fees
8 Oct - 9 Oct
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
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.

11. 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, (34 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is AU$612
includes taxes & fees
1 Oct - 2 Oct
5 Miles from Holiday World sleeps 11+ —Family Escape
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 AU$293
includes taxes & fees
1 Oct - 2 Oct
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
A white house with green shutters, a covered porch, and a small garden.

13. Cozy Vintage House. Home in Fulda, Indiana

Cozy Vintage House. Home in Fulda, Indiana
Fulda
10.0 out of 10, Exceptional, (20 reviews)
"The house was wonderful! So quaint and comfortable."
United States
Samantha I.
The price is AU$551
includes taxes & fees
2 Oct - 3 Oct
Cozy Vintage House. Home in Fulda, Indiana
A modern kitchen with dark cabinets, stainless steel appliances, and a wooden dining table.

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, (28 reviews)
"Awesome quiet place highly recommend!!!"
United States
Bradley D.
The price is AU$468
includes taxes & fees
5 Oct - 6 Oct
Charming and private 3-bedroom farmhouse in lovely Evanston with WiFi, AC.
A modern kitchen with white cabinets, stainless steel appliances, and pendant lighting.

15. 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 AU$723
includes taxes & fees
1 Oct - 2 Oct
Corner Bungalow: Newly Renovated, Spacious & Open, Central & Convenient.
A bedroom with a bunk bed, a single bed, a wooden floor, a bookshelf, and a window with curtains.

16. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (13 reviews)
"We absolutely loved this property! It was very close to local amenities like Holiday World and Santa’s candy shop. The property was immaculately maintained and well decorated. The beds were comfortable, showers were hot, and little added touches like the s'mores supplies were a great surprise! My small boys (5 and 2) shared the kid’s room and we loved that the house had a few toys for the kids to enjoy. The floor bed and bunk bed with a top tent were a huge hit. The stairs to the basement were...
United States
Samantha M.
The price is AU$820
includes taxes & fees
5 Oct - 6 Oct
Run Away Reindeer Retreat
A single-story house with a gabled roof, white shutters, and a front porch.

17. 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, (4 reviews)
"The property was conveniently located within all of our planned attractions."
United States
Lavar B.
The price is AU$516
includes taxes & fees
30 Sept - 1 Oct
3-bedroom Cozy Home Close to Santa Claus, IN and Holiday World
A spacious living room with a fireplace, a large window, and a high ceiling with exposed beams.

18. Family Friendly Lakehouse with great views!

Family Friendly Lakehouse with great views!
Jasper
10.0 out of 10, Exceptional, (13 reviews)
"Very beautiful and comfortable house for our stay"
United States
James S.
The price is AU$614
includes taxes & fees
30 Sept - 1 Oct
Family Friendly Lakehouse with great views!
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
9.4 out of 10, Exceptional, (3 reviews)
"Great place not far from downtown Henderson. Very quiet and comfortable. Hosts very responsive!"
United States
Amanda J.
The price is AU$463
includes taxes & fees
5 Oct - 6 Oct
The Homestead House
Room

20. Historic house

Historic house
Poseyville
8.4 out of 10, Very good, (11 reviews)
"Nice location"
United States
Charlene J.
The price is AU$586
includes taxes & fees
1 Oct - 2 Oct
Historic house
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

Hyatt Place Evansville

Hyatt Place Evansville

10/10 Excellent
"My favorite hotel to stay at in Evansville. Great location, close to many restaurants. Staff is amazing, especially TJ. Very friendly and helpful. Thank you."
Clinton 3-night trip
Posted 8 hours ago
Hyatt Place Evansville

Find out more about Southwestern Indiana

Southwestern Indiana Holiday Homes information

Number of reviews
220
Accommodation
123 Holiday Homes
Lowest Price
AU$236
Highest Price
AU$820