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Southwestern Indiana Vacation Rentals

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Check prices for these dates

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

Our top choices for Southwestern Indiana vacation rentals

A wooden interior with a television, wooden cabinets, and a plant.

1. Guest House with acreage to explore.

Guest House with acreage to explore.
Tennyson
9.6 out of 10, Exceptional, (75 reviews)
"Nice quaint place to stay. 10/10 would recommend and stay if in the area again"
United States
Chasity D.
The price is CA $204
CA $248 total
includes taxes & fees
Nov 23 - Nov 24
Guest House with acreage to explore.
A cozy cabin interior with a sofa, dining table, and chairs.

2. Yellow Banks Log Cabin with Lake Views

Yellow Banks Log Cabin with Lake Views
Dale
8.8 out of 10, Excellent, (29 reviews)
"We had a wonderful stay. Very quiet and peaceful"
United States
LIsa B.
The price is CA $250
CA $417 total
includes taxes & fees
Nov 15 - Nov 16
Yellow Banks Log Cabin with Lake Views
A rustic wooden building with a covered porch and a picnic table.

3. Yellow Banks Log Cabin With Waterfront Views

Yellow Banks Log Cabin With Waterfront Views
Dale
9.8 out of 10, Exceptional, (8 reviews)
"This was a quiet, clean, and convenient little cabin close to Holiday World which is what we stayed for. "
United States
Ashley J.
The price is CA $221
CA $382 total
includes taxes & fees
Nov 17 - Nov 18
Yellow Banks Log Cabin With Waterfront Views
A door with two windows, each with horizontal blinds, leading to a view of a grassy area and a body of water.

4. Tranquil Hideaway: Your Private Lakefront Retreat

Tranquil Hideaway: Your Private Lakefront Retreat
Dale
9.4 out of 10, Exceptional, (14 reviews)
"The property was ideal. We have family in nearby Tennyson, and this was a perfect place to stay and visit. The host was very responsive, and the stay was pleasant and relaxing. "
United States
Jim E.
The price is CA $158
CA $410 total
includes taxes & fees
Nov 23 - Nov 24
Tranquil Hideaway: Your Private Lakefront Retreat
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.

5. 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, (35 reviews)
"Gr8 home base for our stay between business meetings in the area."
United States
Darren S.
The price is CA $353
CA $560 total
includes taxes & fees
Nov 15 - Nov 16
5 Miles from Holiday World sleeps 11+ —Family Escape
A spacious living room with a wooden coffee table, a TV mounted on the wall, and a ceiling fan.

6. Barn in the Burgh — Barndominium Sleeps 12 · Game Room

Barn in the Burgh — Barndominium Sleeps 12 · Game Room
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is CA $259
CA $723 total
includes taxes & fees
Nov 30 - Dec 1
Barn in the Burgh — Barndominium Sleeps 12 · Game Room
A room with a white door, a wooden floor, and a wall with decorative butterfly and flower art.

7. 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, (30 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 CA $141
CA $265 total
includes taxes & fees
Nov 15 - Nov 16
Spacious 1450 sf 2 BR Private Suite w/Dog Fe
A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

8. 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, (45 reviews)
"Great location, quiet but still close to shopping and restaurants. Use of the garage was a plus as it was raining the day we were packing up to leave."
United States
chris g.
The price is CA $144
CA $401 total
includes taxes & fees
Nov 16 - Nov 17
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
A white house with green shutters, a covered porch, and a small garden.

9. Cozy Vintage House. Home in Fulda, Indiana

Cozy Vintage House. Home in Fulda, Indiana
Fulda
10.0 out of 10, Exceptional, (22 reviews)
"The house is just as described on the website. It is within 10 minutes to Holiday world, the beds were very comfortable. Excellent water pressure. The only complaint is there’s very little cell service in the area. I would definitely rent this place again."
United States
Penny F.
The price is CA $199
CA $381 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Vintage House. Home in Fulda, Indiana
A modern kitchen with wooden flooring, stainless steel appliances, a dining area with a view, and a 'GROCERY' sign.

10. Run Away Reindeer Retreat

Run Away Reindeer Retreat
Clay Township
9.6 out of 10, Exceptional, (13 reviews)
"This property was great for our overnight for Holiday World."
United States
Donna J.
The price is CA $408
CA $629 total
includes taxes & fees
Dec 7 - Dec 8
Run Away Reindeer Retreat
A living room with a green sofa, two armchairs, a coffee table, and a cityscape painting.

11. 1 bd/1ba Apt near Haynies Corner

1 bd/1ba Apt near Haynies Corner
Evansville
9.8 out of 10, Exceptional, (7 reviews)
"Located a short walk to about anything downtown. Our host Jada was extremely helpful and accommodating. She gave wonderful recommendations on places to take my wife for our anniversary dinner. The House is a bit older but very clean and updated with about everything you need provided. Shampoo, coffee, cereal, stocked kitchen, and even wine for a fair charge that we ended up enjoying. My only negative is the living room curtains don’t provide much privacy at night (all the other rooms are fine),...
United States
Jesse U.
The price is CA $117
CA $244 total
includes taxes & fees
Nov 15 - Nov 16
1 bd/1ba Apt near Haynies Corner
A modern hotel room with a large flat-screen TV, a dining area with a chandelier, and a cozy seating arrangement.

12. The Chic Shack | Centrally Located 2BR/1BA Home

The Chic Shack | Centrally Located 2BR/1BA Home
Evansville
10.0 out of 10, Exceptional, (3 reviews)
"Only stayed one night during the week, but the neighborhood was quiet, the location was convenient for my business and the house had everything I needed. Slept very well and would book this one again."
United States
Jake T.
The price is CA $149
CA $298 total
includes taxes & fees
Nov 15 - Nov 16
The Chic Shack | Centrally Located 2BR/1BA Home
A neatly made bed with a white duvet and a yellow throw, a bedside table with a lamp, and decorative wall art.

13. Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh

Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
Newburgh
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place! The outdoor lighting is really cool with the trees lit up and the house numbers lit up, as well. Only a 5 minute drive to the shops and restaurants on the river. "
United States
stephanie b.
The price is CA $199
CA $354 total
includes taxes & fees
Nov 20 - Nov 21
Cypress Suites 7A - KING 2BD/1BA Apt in Newburgh
A modern kitchen with white cabinetry, stainless steel appliances, and a patterned rug.

14. RiverStone Retreat B

RiverStone Retreat B
Newburgh
The price is CA $112
CA $228 total
includes taxes & fees
Nov 15 - Nov 16
RiverStone Retreat B
A bedroom with a wooden wall panel, a bed with white bedding, and a small shelf with decorative items.

15. Princeton Suite 7 - QUEEN 1BD/1BA Apt

Princeton Suite 7 - QUEEN 1BD/1BA Apt
Princeton
The price is CA $107
CA $227 total
includes taxes & fees
Nov 18 - Nov 19
Princeton Suite 7 - QUEEN 1BD/1BA Apt
A room with a bed, a blue armchair, a small table, a round ottoman, and a brick wall with decorative items.

16. The Cardinal 810 D -3BR-1BA Apt

The Cardinal 810 D -3BR-1BA Apt
Evansville
10.0 out of 10, Exceptional, (1 review)
The Cardinal 810 D -3BR-1BA Apt
A living room with a sofa, coffee table, bookshelf, and a window with curtains.

17. River City Retreat | Stylish 1BR/1BA Apartment

River City Retreat | Stylish 1BR/1BA Apartment
Evansville
8.8 out of 10, Excellent, (6 reviews)
"great location for visiting my son at University of Evansville."
United States
Amy S.
River City Retreat | Stylish 1BR/1BA Apartment
A two-story house with a red door, a small porch, and a well-maintained lawn.

18. 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.
1520 Howard St B "HCB"
A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

19. 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, (15 reviews)
"Great property close to Golf Course . Easy access, safe neighborhood and quiet. Couldn’t have had a better stay"
United States
Randy S.
The price is CA $284
CA $801 total
includes taxes & fees
Nov 16 - Nov 17
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
A modern interior with a wooden floor, a dining area with a round table and chairs, a sofa with patterned cushions, and a wall-mounted abstract art piece.

20. The Downtown Gem

The Downtown Gem
Jasper
The price is CA $270
CA $503 total
includes taxes & fees
Dec 4 - Dec 5
The Downtown Gem
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

A Hampton Inn by Hilton hotel with a well-lit entrance, a landscaped lawn, and a clear sky.
Hampton Inn Jasper

Hampton Inn Jasper

Hampton Inn Jasper
Jasper

10/10 Excellent

Room was clean, staff was friendly
Canada
Ghislain
Reviewed January 15, 2026
Hampton Inn Jasper

Find out more about Southwestern Indiana

Everything you need to know about Southwestern Indiana vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southwestern Indiana vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southwestern Indiana vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southwestern Indiana vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southwestern Indiana. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Southwestern Indiana vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Southwestern Indiana vacation rentals we have selected for you start as low as CA $77 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Southwestern Indiana rentals

At Expedia, we put the best Southwestern Indiana vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southwestern Indiana rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southwestern Indiana vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southwestern Indiana. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.