Photo by Dubois County Visitors Center

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Southwestern Indiana holiday rentals

A rustic cabin interior with a spiral staircase leading to a loft bedroom, a kitchen area, and a dining space.

1. Patoka 4 Seasons

Patoka 4 Seasons
3.0 star property
Eckerty
8.0 out of 10, Very good, (4 reviews)
"Nice quiet place. Loved the pool."
United States
Anna
The price is Rp2.785.090
Rp4.375.125 total
includes taxes & fees
1 Dec - 2 Dec
Patoka 4 Seasons
A wooden door with a decorative knocker and a lantern above it.

2. Pleasant Grove Farm LLC

Pleasant Grove Farm LLC
3.0 star property
Lyons
9.6 out of 10, Exceptional, (105 reviews)
"This is our favorite place to stay every Labor Day weekend. It’s home away from home!"
United States
Craig
The price is Rp2.531.900
Rp2.835.728 total
includes taxes & fees
12 Nov - 13 Nov
Pleasant Grove Farm LLC
A living room with a fireplace, leather sofas, and a clock on the wall.

3. Illinois Vacation Rental Home: Pets Welcome

Illinois Vacation Rental Home: Pets Welcome
3.0 star property
Palestine
10.0 out of 10, Exceptional, (1 review)
The price is Rp2.586.155
Rp6.257.772 total
includes taxes & fees
24 Nov - 25 Nov
Illinois Vacation Rental Home: Pets Welcome
A cozy living room with a stone fireplace, leather furniture, and large windows.

4. Waterfront Gem w/ Private Dock on Sullivan Lake!

Waterfront Gem w/ Private Dock on Sullivan Lake!
3.0 star property
Sullivan
Waterfront Gem w/ Private Dock on Sullivan Lake!
A spacious kitchen with modern appliances, a dining area with a glass-top table, and a ceiling fan.

5. Updated Robinson Vacation Rental w/ Fireplace!

Updated Robinson Vacation Rental w/ Fireplace!
3.0 star property
Robinson
The price is Rp4.684.015
Rp7.899.166 total
includes taxes & fees
13 Nov - 14 Nov
Updated Robinson Vacation Rental w/ Fireplace!
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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Find holiday rentals that suit your style

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Apartments
Apartments
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Cabins
Cabins

Top Southwestern Indiana Hotel Reviews

A restaurant with multiple dining tables set for guests, a bar area with a variety of bottles, and a wooden accent wall with two flat-screen TVs.
Hampton Inn & Suites Downtown Owensboro/Waterfront

Hampton Inn & Suites Downtown Owensboro/Waterfront

Hampton Inn & Suites Downtown Owensboro/Waterfront
Owensboro

10/10 Excellent

Well situated and comfortable hotel on the river bank in Owensboro
United Kingdom
Owen
Reviewed June 22, 2022
Hampton Inn & Suites Downtown Owensboro/Waterfront

Find out more about Southwestern Indiana

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Look no further and take a look at our great range of rental properties in Southwestern Indiana!