Webster County Vacation Rentals from ￥24,016: Search Short-Term Rentals

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Our top choices for Webster County vacation rentals

A bathroom with a vanity, a mirror, a sink, a towel rack, and a window with a view of a garden.

1. Union Station Union Station

Madisonville

Rhonda P.

￥50,410 total

includes taxes & fees

Oct 25 - Oct 26

A wooden observation tower with a small deck and stairs, surrounded by trees.

2. Charming Treehouse with Lake View and Access

Utica

Lori

￥24,016 total

includes taxes & fees

Oct 20 - Oct 21

A wooden deck with a table and chairs, overlooking a grassy field and a sunset.

3. Charming cabin with amazing views located on Toontucky Farms

White Plains

Brandon L.

￥26,381 total

includes taxes & fees

Oct 20 - Oct 21

A two-story house with a porch, a front door, and a small front yard.

4. Beautiful Southern Home

Sacramento

Courtney W.

￥63,732 total

includes taxes & fees

Oct 20 - Oct 21

A dark wood TV stand with a flat-screen TV and a remote control.

5. Sweet Dreams in Sacramento

Sacramento

Paul R.

￥38,505 total

includes taxes & fees

Nov 1 - Nov 2

A spacious kitchen with a central island, wooden cabinets, and a ceiling fan.

6. Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.

Elizabethtown

Lisa L.

￥25,741 total

includes taxes & fees

Oct 20 - Oct 21

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

7. Brand New, Conveniently Located In Marion, KY

Marion

Julie S.

￥41,111 total

includes taxes & fees

Oct 21 - Oct 22

A neatly made bed with white bedding and two rolled towels, a wooden headboard, and a floor lamp.

8. Henderson Haven / KING 2BD/1BA Apartment

Henderson

Joel

￥31,770 total

includes taxes & fees

Oct 21 - Oct 22

A rustic cabin with a stone foundation, wooden siding, and a covered porch.

9. Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro

Utica

Andrea S.

￥45,661 total

includes taxes & fees

Nov 18 - Nov 19

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

10. 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.

￥46,797 total

includes taxes & fees

Oct 28 - Oct 29

A kitchen with wooden cabinets, a stove, and a dining area with a table and chairs.

11. Rustic 1 bedroom/1 bath home w/loft that sleeps 8. Near Shawnee National Forest

Elizabethtown

Mustafa

￥36,476 total

includes taxes & fees

Oct 20 - Oct 21

A modern kitchen with white cabinets, a wooden island, and a gray sofa with yellow pillows.

12. Lake Country House on City Square

Princeton

Stacey S.

￥45,815 total

includes taxes & fees

Oct 20 - Oct 21

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

13. The Homestead House

Henderson

Amanda J.

￥52,450 total

includes taxes & fees

Oct 20 - Oct 21

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

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

Owensboro

Brad H.

￥33,467 total

includes taxes & fees

Oct 20 - Oct 21

A single-story house with a front porch, surrounded by a well-maintained lawn and two large trees.

15. Quiet 3-bedroom house in Mexico, Kentucky

Marion

Sue M.

￥34,173 total

includes taxes & fees

Oct 25 - Oct 26

A modern kitchen with a white countertop, a stainless steel sink, and grey cabinets.

16. The Mint Julep! Upstairs 3BD 2BA Next to Brewery

Henderson

Sylvia W.

￥61,888 total

includes taxes & fees

Oct 21 - Oct 22

A blue triangular building with a porch, two chairs, and a gravel driveway.

17. The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit

Cave-In-Rock Precinct

Deborah K

￥57,479 total

includes taxes & fees

Nov 5 - Nov 6

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

18. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

Owensboro

John

￥54,662 total

includes taxes & fees

Oct 26 - Oct 27

A modern apartment with a kitchen, dining area, and living room.

19. Brand new, conveniently located 2 bedroom apartment in Marion, KY

Marion

Tim O.

￥41,111 total

includes taxes & fees

Oct 20 - Oct 21

A bedroom with a bed, a ceiling fan, a nightstand, a lamp, and a door.

20. Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB

Owensboro

￥104,878 total

includes taxes & fees

Oct 22 - Oct 23

View all properties

Find vacation rentals that suit your style

Apartments

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Webster County Hotel Reviews

Days Inn by Wyndham Madisonville

8/10 Good

"Could not get volume on TV Bathroom sink faucet trickle"

The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit

10/10 Excellent

"We wanted a place “to get away from it all.” We got our wish and then some. The cabin is beautifully decorated and clean yet so very comfortable and quiet tucked into the hills of gorgeous Southeastern Illinois. We spent a lot of time relaxing and enjoying the cabin. We also got out and saw some of the sites and natural beauty of the area. The hostess thinks of everything. We will be back."

Holiday Inn Express & Suites Madisonville by IHG

8/10 Good

"Everything was nice and clean The staff was hospitable. The bed was very comfortable. I slept soundly. Got to watch a South Park marathon all week. The only minor critique is the price was a bit high and I would’ve preferred if they had a spa or hot tub. I skipped the breakfast because I had my own food but l’m sure it was nice."

Hampton Inn Owensboro South

10/10 Excellent

"I can not say enough about the kindness of the staff! Wow! Not just check in but throughout our staff and 90% that we passed in the hallways! Incredible people! Hotel a little noisy first thing but nothing that would make me think twice - just different schedules. I would definitely recommend! Pool was closed for the season so that was the only downside but we have come to realize that was some with all the pools on our trip and it mentions right on website if you read! Thank you !!!"

Find out more about Webster County

Vacation Apartments in Webster County

Search for Vacation rentals in Webster County on Expedia! You can easily find your home rentals, villas, Vacation apartments in Webster County using one of the methods below:

View our selection of featured Vacation rentals in Webster County
Use the map to find apartments and other Vacation homes in the Webster County neighbourhood you prefer
Enter your travel dates to view the best deals on Vacation rentals in Webster County while they last

Look no further and take a look at our great range of rental properties in Webster County!

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Webster County vacation rentals

1. Union Station Union Station

2. Charming Treehouse with Lake View and Access

3. Charming cabin with amazing views located on Toontucky Farms

4. Beautiful Southern Home

5. Sweet Dreams in Sacramento

6. Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.

7. Brand New, Conveniently Located In Marion, KY

8. Henderson Haven / KING 2BD/1BA Apartment

9. Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro

10. The Bluegrass Barbie

11. Rustic 1 bedroom/1 bath home w/loft that sleeps 8. Near Shawnee National Forest

12. Lake Country House on City Square

13. The Homestead House

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

15. Quiet 3-bedroom house in Mexico, Kentucky

16. The Mint Julep! Upstairs 3BD 2BA Next to Brewery

17. The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit

18. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

19. Brand new, conveniently located 2 bedroom apartment in Marion, KY

20. Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB

Find vacation rentals that suit your style

Top Webster County Hotel Reviews

Days Inn by Wyndham Madisonville

Envi Boutique Hotel

Super 8 by Wyndham Owensboro

The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit

Wingate by Wyndham Owensboro

Holiday Inn Express & Suites Madisonville by IHG

Charming Treehouse with Lake View and Access

Hampton Inn Owensboro South

Holiday Inn Express Henderson N Evansville South by IHG

Find out more about Webster County

Vacation Apartments in Webster County

Vacation Rentals in Webster County

Change your mind

Treat yourself

Be picky

Our top choices for Webster County vacation rentals

1. Union Station Union Station

2. Charming Treehouse with Lake View and Access

3. Charming cabin with amazing views located on Toontucky Farms

4. Beautiful Southern Home

5. Sweet Dreams in Sacramento

6. Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.

7. Brand New, Conveniently Located In Marion, KY

8. Henderson Haven / KING 2BD/1BA Apartment

9. Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro

10. The Bluegrass Barbie

11. Rustic 1 bedroom/1 bath home w/loft that sleeps 8. Near Shawnee National Forest

12. Lake Country House on City Square

13. The Homestead House

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

15. Quiet 3-bedroom house in Mexico, Kentucky

16. The Mint Julep! Upstairs 3BD 2BA Next to Brewery

17. The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit

18. 4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World

19. Brand new, conveniently located 2 bedroom apartment in Marion, KY

20. Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB

Find vacation rentals that suit your style

Top Webster County Hotel Reviews

Days Inn by Wyndham Madisonville

Find out more about Webster County

Vacation Apartments in Webster County