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

Search Cottages 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 cottages

1. 2-bedroom cottage with hot tub in charming Loogootee

2-bedroom cottage with hot tub in charming Loogootee
Loogootee
9.6 out of 10, Exceptional, (4 reviews)
"Cozy little cottage. We just had a one night getaway and it was great to unwind."
United States
Kelsey K.
The price is SAR 591
SAR 813 total
includes taxes & fees
4 Dec - 5 Dec
2-bedroom cottage with hot tub in charming Loogootee

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 SAR 525
SAR 589 total
includes taxes & fees
5 Nov - 6 Nov
Pleasant Grove Farm LLC

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 SAR 537
SAR 1,299 total
includes taxes & fees
10 Nov - 11 Nov
Illinois Vacation Rental Home: Pets Welcome

4. Fireflies and night skies!

Fireflies and night skies!
French Lick
10.0 out of 10, Exceptional, (7 reviews)
"Super clean, lovely property in the woods. Very quiet and relaxing. Definitely plenty of fireflies at night too!"
United States
Roger S.
The price is SAR 657
SAR 908 total
includes taxes & fees
4 Nov - 5 Nov
Fireflies and night skies!

5. 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!
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