Henderson County courthouse with a golden dome and columns.

Henderson Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Henderson vacation homes

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

1. The Homestead House

The Homestead House
Henderson
9.4 out of 10, Exceptional, (3 reviews)
"The house is nice. It was clean and comfortable. I do feel the price was a bit high for the quality of the furnishings, materials, etc. Low end items look nice but aren’t very comfortable (e.g., couch and bed). The owner was nice and accommodating. Just felt a bit overpriced for what we got, otherwise 5 stars."
United States
F S.
The price is CA $231
CA $468 total
includes taxes & fees
Sep 28 - Sep 29
The Homestead House
A modern living room with a sectional sofa, a coffee table, and decorative plants.

2. Trendy Two bedroom home centrally located near UE

Trendy Two bedroom home centrally located near UE
Evansville
9.0 out of 10, Wonderful, (11 reviews)
"Would stay again"
United States
Scott D.
The price is CA $119
CA $273 total
includes taxes & fees
Sep 28 - Sep 29
Trendy Two bedroom home centrally located near UE
A dining area with a wooden table and chairs, a bookshelf with books and decorative items, and a pet bed in the corner.

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

Green Roof Inn | Centrally Located 2BR/1BA Home
Evansville
8.4 out of 10, Very good, (6 reviews)
"A lovely little bungalow that is near the Swonder Ice Rink and some amazing local restaurants and coffee shops."
United States
Steph M.
The price is CA $146
CA $308 total
includes taxes & fees
Oct 4 - Oct 5
Green Roof Inn | Centrally Located 2BR/1BA Home
A two-story house with a red door, a small porch, and a well-maintained lawn.

4. 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.
The price is CA $100
CA $232 total
includes taxes & fees
Oct 1 - Oct 2
1520 Howard St B "HCB"
A modern hotel room with a large flat-screen TV, a dining area with a chandelier, and a cozy seating arrangement.

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

The Chic Shack | Centrally Located 2BR/1BA Home
Evansville
10.0 out of 10, Exceptional, (2 reviews)
"It felt like home in this space. All the extra throw blankets to be warm and cozy. The host is very easy to work with."
United States
Meisha W.
The price is CA $145
CA $308 total
includes taxes & fees
Sep 30 - Oct 1
The Chic Shack | Centrally Located 2BR/1BA Home
A living room with a TV, sofa, coffee table, and a dining area with a chair and table.

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

Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
Evansville
The price is CA $102
CA $298 total
includes taxes & fees
Oct 1 - Oct 2
Deaconess Gateway 3 miles, Quiet, Open, 1BDRM, Private Parking & More!
A modern kitchen with white cabinets, stainless steel appliances, and pendant lighting.

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

Corner Bungalow: Newly Renovated, Spacious & Open, Central & Convenient.
Evansville
10.0 out of 10, Exceptional, (5 reviews)
"Great place to stay "
United States
Dartain W.
The price is CA $281
CA $740 total
includes taxes & fees
Oct 1 - Oct 2
Corner Bungalow: Newly Renovated, Spacious & Open, Central & Convenient.
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, (44 reviews)
"We have absolutely loved it here the wildlife the owners are amazing. I hope that next time we’re in town will be able to stay here again."
United States
Kristen J.
The price is CA $130
CA $389 total
includes taxes & fees
Oct 8 - Oct 9
Charming Retreat near Historic Newburgh, Evansville and Henderson Kentucky.
A modern kitchen with white cabinetry, a central island with bar stools, and pendant lighting.

9. 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, (13 reviews)
"Property was as advertised - Ryan was excellent to work with. I wouldn’t hesitate to stay at this property again!"
United States
Jacob O.
The price is CA $239
CA $771 total
includes taxes & fees
Oct 4 - Oct 5
Luxury 4BR Forest Retreat w/ Theater, Game Room, Modern Design & Total Privacy
A modern kitchen with a central island, bar stools, stainless steel appliances, and a brick accent wall.

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

Rooftop Views | Entire Building | 4BR/5BA | Downtown Evansville | Groups up t...
Downtown Evansville
10.0 out of 10, Exceptional, (1 review)
"Everything was nice and clean. Kitchens were fully stocked. Would be nice if the United were connected inside 1st and 2nd floor but otherwise it was very nice."
United States
Barbara W.
The price is CA $322
CA $1,085 total
includes taxes & fees
Sep 28 - Sep 29
Rooftop Views | Entire Building | 4BR/5BA | Downtown Evansville | Groups up t...
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

Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
Newburgh
10.0 out of 10, Exceptional, (20 reviews)
"Great Stay!"
United States
Julia F.
The price is CA $180
CA $600 total
includes taxes & fees
Sep 29 - Sep 30
Barn in the Burgh — Barndominium Sleeps 12 · Game Room + Event Space
A covered porch with a wooden floor, a bench, and a small Christmas tree.

12. Bluegrass Bungalow 2 bedrooms with large porch

Bluegrass Bungalow 2 bedrooms with large porch
Owensboro
9.6 out of 10, Exceptional, (44 reviews)
"This was a great house in a perfect location for our stay in Owensboro. Really enjoyed our stay."
United States
Jennifer A.
The price is CA $144
CA $261 total
includes taxes & fees
Sep 28 - Sep 29
Bluegrass Bungalow 2 bedrooms with large porch
A living room with a fireplace, a ceiling fan, and a flat-screen TV.

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

Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
Owensboro
9.8 out of 10, Exceptional, (36 reviews)
"Very nice home with great amenities and owner was really great and helpful with any questions and needs."
United States
Brad H.
The price is CA $140
CA $281 total
includes taxes & fees
Sep 28 - Sep 29
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
A modern kitchen with dark cabinets, stainless steel appliances, a granite countertop, and a dishwasher.

14. 1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio

1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio
Owensboro
10.0 out of 10, Exceptional, (24 reviews)
"We were in town for my daughter’s graduation, it was a 10 out of 10. We couldn’t have asked for a better place to stay. "
United States
Johnny J.
The price is CA $156
CA $438 total
includes taxes & fees
Sep 28 - Sep 29
1 King Bed + 1 Queen Bed + 2 Full Bathrooms Kitchen + Laundry Room + Patio
A modern living room with a grey sofa, a coffee table, and a dining area with wooden chairs and a table.

15. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World
Owensboro
10.0 out of 10, Exceptional, (43 reviews)
"Extremely well-maintained property stocked with everything you could need. Host was accessible and very helpful."
United States
John
The price is CA $205
CA $494 total
includes taxes & fees
Sep 28 - Sep 29
4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World
A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

16. The Bluegrass Barbie

The Bluegrass Barbie
Owensboro
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Jessica S.
The price is CA $132
CA $422 total
includes taxes & fees
Oct 26 - Oct 27
The Bluegrass Barbie
A wooden-floored hallway with a staircase, a bookshelf, and a door with a stained glass window.

17. Downtown Dream in Owensboro Ky

Downtown Dream in Owensboro Ky
Owensboro
9.4 out of 10, Exceptional, (24 reviews)
"Everything was great, perfect location downtown. "
United States
James K.
The price is CA $133
CA $648 total
includes taxes & fees
Sep 29 - Sep 30
Downtown Dream in Owensboro Ky
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.

18. Cozy Cottage home

Cozy Cottage home
Owensboro
10.0 out of 10, Exceptional, (4 reviews)
"Was very nice clean and host was great"
United States
falesha p.
The price is CA $146
CA $334 total
includes taxes & fees
Sep 29 - Sep 30
Cozy Cottage home
A modern living room with a sofa, coffee table, and a dining table.

19. Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat

Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
Owensboro
The price is CA $165
CA $511 total
includes taxes & fees
Oct 4 - Oct 5
Sip & Stay on Owensboro’s Whiskey Row Stylish 2BR Retreat
A bedroom with a bed, two bedside tables, a ceiling fan, a neon sign, and a floral painting on the wall.

20. Cozy 2-bedroom house in Owensboro KY

Cozy 2-bedroom house in Owensboro KY
Owensboro
10.0 out of 10, Exceptional, (2 reviews)
"Great stay great host"
United States
BPCAT 0.
The price is CA $184
CA $281 total
includes taxes & fees
Oct 4 - Oct 5
Cozy 2-bedroom house in Owensboro KY
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 Henderson Hotel Reviews

Holiday Inn Express Henderson N Evansville South by IHG

Holiday Inn Express Henderson N Evansville South by IHG

10/10 Excellent
"Na"
Audrey 1-night trip
Posted 23 hours ago
Holiday Inn Express Henderson N Evansville South by IHG

Find out more about Henderson

Henderson Vacation Homes information

Number of reviews
230
Accommodation
121 Vacation Homes
Lowest Price
CA $232
Highest Price
CA $1,085

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