Henderson Holiday Houses

Henderson County courthouse with a golden dome and columns.

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Our top choices for Henderson holiday homes

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

1. The Homestead House

Henderson

F S.

includes taxes & fees

20 Sept - 21 Sept

A modern kitchen with white cabinets, a dishwasher, and a wooden countertop.

2. House of Color A / KING 1BD/1BA Apt

Evansville

Ronald G.

includes taxes & fees

20 Sept - 21 Sept

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.

includes taxes & fees

23 Sept - 24 Sept

A dining area with a wooden table and chairs, a bookshelf with books and decorative items, and a pet bed in the corner.

4. Green Roof Inn | Centrally Located 2BR/1BA Home

Evansville

Steph M.

includes taxes & fees

20 Sept - 21 Sept

A living room with a sofa, armchairs, a coffee table, a fireplace, a television, and a large window.

5. Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.

Newburgh

Kristen J.

includes taxes & fees

21 Sept - 22 Sept

A teal front door with a wreath, two potted plants, and a black and white checkered doormat with "hello" written on it.

6. Leaning House of Haynie | Trendy 2BR/1BA Apartment

Evansville

Kathryn H.

includes taxes & fees

20 Sept - 21 Sept

A bedroom with a bed, a nightstand, a chair, and a window with curtains.

7. Color Pop Casa | 2BR/1BA Townhome near Ford Center

Downtown Evansville

Alexis R.

includes taxes & fees

18 Sept - 19 Sept

A living room with a TV, sofa, coffee table, and a dining area with a chair and table.

8. Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!

Evansville

includes taxes & fees

22 Sept - 23 Sept

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

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

Evansville

Dartain W.

includes taxes & fees

12 Oct - 13 Oct

A modern bedroom with a large bed, a bedside table with a lamp, and a window with curtains.

10. 2 KING BR/1BA In Evansville, IN Fenced in Yard. Fast wifi. Washer and Dryer

Evansville

"This property is not what you see in the pictures. It's shabby and rough inside, including missing molding, patched walls and scuffed up furniture. We walked in and there were flies all over the kitchen and dead on the counter. It probably was a temporary problem, but not something you want to walk in on when you're paying for the space. The beds were made, but not sure that the house had been cleaned recently based on the kitchen. The outside of the house is also rough. Parking on the...

Heather M.

includes taxes & fees

20 Sept - 21 Sept

A spacious kitchen with a large island, built-in appliances, and a ceiling fan.

11. Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space

Newburgh

Mary P.

includes taxes & fees

22 Sept - 23 Sept

A covered porch with a wooden floor, a bench, and a small Christmas tree.

12. Bluegrass Bungalow 2 bedrooms with large porch

Owensboro

Jennifer A.

includes taxes & fees

20 Sept - 21 Sept

A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

13. Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy

Evansville

Jacob O.

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a central island, bar stools, stainless steel appliances, and a brick wall.

14. Rooftop Views | Entire Building | 4BR/5BA | Downtown Evansville | Groups up t...

Downtown Evansville

Barbara W.

includes taxes & fees

12 Oct - 13 Oct

A living room with a fireplace, a ceiling fan, and a flat-screen TV.

15. Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!

Owensboro

Brad H.

includes taxes & fees

20 Sept - 21 Sept

A modern living room with a grey sofa, a coffee table, and a dining area with wooden chairs and a table.

16. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

Owensboro

John

includes taxes & fees

4 Oct - 5 Oct

A neatly made bed with a 'WELCOME' pillow, a bedside table with a lamp, a ceiling fan, and a 'STAY awhile' sign on the wall.

17. Cozy Cottage home

Owensboro

falesha p.

includes taxes & fees

28 Sept - 29 Sept

A modern kitchen with dark cabinets, stainless steel appliances, a granite countertop, and a dishwasher.

18. 1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

Owensboro

Johnny J.

includes taxes & fees

28 Sept - 29 Sept

A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

19. The Bluegrass Barbie

Owensboro

"After staying for several weeks, we can say with confidence that our host, Kelsey, and the Bluegrass Barbie house exceeded our expectations! Kelsey was so friendly and made our experience an easy one. She was accessible to us, very responsive, and accommodating throughout our stay. She made the process seamless. The home has great curb appeal and is located in a nice neighborhood where we felt very safe. We felt welcomed when we walked in the door. Inside, the home was very clean throughout...

Jessica S.

includes taxes & fees

30 Sept - 1 Oct