Southwestern Indiana Vacation Homes

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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

Lynnville

Patricia G.

HK$2,180 total

includes taxes & fees

6 Oct - 7 Oct

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

Huntingburg

James B.

HK$1,529 total

includes taxes & fees

30 Sept - 1 Oct

A modern living room with a sectional sofa, a coffee table, and decorative plants.

3. Trendy Two bedroom home centrally located near UE

Evansville

Scott D.

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

Gentryville

Jennifer C.

HK$2,996 total

includes taxes & fees

30 Sept - 1 Oct

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

Newburgh

Julia F.

HK$3,060 total

includes taxes & fees

30 Sept - 1 Oct

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.

Newburgh

Kristen J.

HK$2,080 total

includes taxes & fees

8 Oct - 9 Oct

A two-story house with a red door, a small porch, and a well-maintained lawn.

7. 1520 Howard St B "HCB"

Evansville

scott c.

HK$1,285 total

includes taxes & fees

4 Oct - 5 Oct

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

Evansville

Steph M.

HK$1,602 total

includes taxes & fees

4 Oct - 5 Oct

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

Evansville

Meisha W.

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

Evansville

Jacob O.

HK$4,041 total

includes taxes & fees

4 Oct - 5 Oct

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

Dale

Darren S.

HK$3,277 total

includes taxes & fees

1 Oct - 2 Oct

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!

Evansville

A white house with green shutters, a covered porch, and a small garden.

13. Cozy Vintage House. Home in Fulda, Indiana

Fulda

HK$2,956 total

includes taxes & fees

30 Sept - 1 Oct

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.

Evanston

Bradley D.

HK$2,469 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with white cabinets, stainless steel appliances, and pendant lighting.

15. Corner Bungalow: Newly Renovated, Spacious & Open, Central & Convenient.

Evansville

Dartain W.

HK$3,987 total

includes taxes & fees

12 Oct - 13 Oct

A bedroom with a bunk bed, a single bed, a wooden floor, a bookshelf, and a window with curtains.

16. Run Away Reindeer Retreat

Clay Township

"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...

Samantha M.

HK$4,174 total

includes taxes & fees

27 Oct - 28 Oct

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

Ferdinand

Lavar B.

HK$2,715 total

includes taxes & fees

4 Oct - 5 Oct

A spacious living room with a fireplace, a large window, and a high ceiling with exposed beams.

18. Family Friendly Lakehouse with great views!

Jasper

James S.

HK$3,251 total

includes taxes & fees

30 Sept - 1 Oct

A modern kitchen with a central island, built-in appliances, and a dining area with a window.

19. The Homestead House

Henderson

Amanda J.

HK$2,448 total

includes taxes & fees

4 Oct - 5 Oct

20. Historic house

Poseyville

Charlene J.

HK$3,066 total

includes taxes & fees

2 Oct - 3 Oct

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Top Southwestern Indiana Hotel Reviews

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."

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