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Our top choices for Webster County holiday rentals

A two-story building with a covered porch and a small staircase.

1. Nice and Quite place to stay

Nice and Quite place to stay
Madisonville
The price is £277
includes taxes & fees
5 Oct - 6 Oct
Nice and Quite place to stay
An open-plan living area with a sofa, two armchairs, a ceiling fan, and a door leading to a balcony.

2. Loop Haven is an awesome place to stay.

Loop Haven is an awesome place to stay.
Madisonville
9.4 out of 10, Exceptional, (14 reviews)
"Nice clean space with room for everything we needed. Host was quick to always keep us up to date on our reservation, check in and check out.One minor issue was resolved immediately. Would stay here again although it's not fenced in on one side so luckily that was not an issue for us."
United States
Dianne K.
The price is £284
includes taxes & fees
5 Oct - 6 Oct
Loop Haven is an awesome place to stay.
A spacious dining area with a large wooden table and chairs, a kitchen with white cabinets, and a ceiling with wooden beams.

3. Littlefield Farmhouse in Princeton, KY

Littlefield Farmhouse in Princeton, KY
Princeton
10.0 out of 10, Exceptional, (45 reviews)
"Great stay! Would definitely go back"
United States
Brandon K.
The price is £156
includes taxes & fees
5 Oct - 6 Oct
Littlefield Farmhouse in Princeton, KY
A wooden deck with a table and chairs, overlooking a grassy field and a sunset.

4. Charming cabin with amazing views located on Toontucky Farms

Charming cabin with amazing views located on Toontucky Farms
White Plains
9.8 out of 10, Exceptional, (9 reviews)
" Stayed for a week very nice place. "
United States
Brandon L.
The price is £129
includes taxes & fees
6 Oct - 7 Oct
Charming cabin with amazing views located on Toontucky Farms
A wooden observation tower with a small deck and stairs, surrounded by trees.

5. Charming Treehouse with Lake View and Access

Charming Treehouse with Lake View and Access
Utica
9.8 out of 10, Exceptional, (121 reviews)
"Awesome place to have some time with family away from everyone."
United States
Lori
The price is £118
includes taxes & fees
5 Oct - 6 Oct
Charming Treehouse with Lake View and Access
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.

Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.
Elizabethtown
10.0 out of 10, Exceptional, (3 reviews)
"Just a wonderful little cabin and extremely helpful host. Loved it"
United States
Jeremiah 33:3 m.
The price is £127
includes taxes & fees
5 Oct - 6 Oct
Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.
A modern apartment with a kitchen, dining area, and living room.

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

Brand new, conveniently located 2 bedroom apartment in Marion, KY
Marion
9.6 out of 10, Exceptional, (18 reviews)
"Very conveniently located and a great experience in every aspect. A great place to stay and will definitely book with this property owner again."
United States
Tim O.
The price is £200
includes taxes & fees
6 Oct - 7 Oct
Brand new, conveniently located 2 bedroom apartment in Marion, KY
A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

8. 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 £226
includes taxes & fees
26 Oct - 27 Oct
The Bluegrass Barbie
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

Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro
Utica
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful spot! The best "
United States
Andrea S.
The price is £218
includes taxes & fees
26 Oct - 27 Oct
Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro
A blue triangular building with a porch, two chairs, and a gravel driveway.

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

The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit
Cave-In-Rock Precinct
10.0 out of 10, Exceptional, (5 reviews)
"Great quiet location! It was very clean and comfy! Will definitely be back again!!"
United States
Deborah K
The price is £270
includes taxes & fees
25 Oct - 26 Oct
The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit
A living room with a fireplace, a ceiling fan, and a flat-screen TV.

11. 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 £153
includes taxes & fees
5 Oct - 6 Oct
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
A kitchen with wooden cabinets, a stove, and a dining area with a table and chairs.

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

Rustic 1 bedroom/1 bath home w/loft that sleeps 8. Near Shawnee National Forest
Elizabethtown
10.0 out of 10, Exceptional, (2 reviews)
"The cabin is lovely. The hosts had all the essentials plus all the little extra things that show they have pride in their property. The cabin is centrally located between several “must-sees” in the Shawnee National Forest. Just of note there are no grocery stores within about 30 minutes of the cabin. I normally don’t pack groceries for vacation and just have them delivered so just know if you normally do that also, it’s not an option. There are several convenience stores close by and a DG...
United States
Kerry O.
The price is £179
includes taxes & fees
5 Oct - 6 Oct
Rustic 1 bedroom/1 bath home w/loft that sleeps 8. Near Shawnee National Forest
A modern kitchen with a central island, built-in appliances, and a dining area with a window.

13. The Homestead House

The Homestead House
Henderson
9.6 out of 10, Exceptional, (4 reviews)
"Great place not far from downtown Henderson. Very quiet and comfortable. Hosts very responsive!"
United States
Amanda J.
The price is £249
includes taxes & fees
12 Oct - 13 Oct
The Homestead House
A single-story house with a front porch, surrounded by a well-maintained lawn and two large trees.

14. Quiet 3-bedroom house in Mexico, Kentucky

Quiet 3-bedroom house in Mexico, Kentucky
Marion
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful country "
United States
Sue M.
The price is £164
includes taxes & fees
5 Oct - 6 Oct
Quiet 3-bedroom house in Mexico, Kentucky
A modern kitchen with white cabinets, a wooden island, and a gray sofa with yellow pillows.

15. Lake Country House on City Square

Lake Country House on City Square
Princeton
9.8 out of 10, Exceptional, (29 reviews)
"Host was great to work with. House was very spacious and comfortable. Will definitely stay again."
United States
Beverly W.
The price is £223
includes taxes & fees
5 Oct - 6 Oct
Lake Country House on City Square
A modern kitchen with a white countertop, a stainless steel sink, and grey cabinets.

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

The Mint Julep! Upstairs 3BD 2BA Next to Brewery
Henderson
10.0 out of 10, Exceptional, (1 review)
"Great location. We would definitely book again."
United States
Sylvia W.
The price is £295
includes taxes & fees
8 Oct - 9 Oct
The Mint Julep! Upstairs 3BD 2BA Next to Brewery
A bedroom with a bed, nightstands, a ceiling fan, and a view into the dining area.

17. 3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown

3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown
Owensboro
The price is £234
includes taxes & fees
6 Oct - 7 Oct
3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

18. Brand New, Conveniently Located In Marion, KY

Brand New, Conveniently Located In Marion, KY
Marion
9.6 out of 10, Exceptional, (17 reviews)
"Unit was exceptionally clean and very well equipped. Great communication and thoughtful welcome treats. We look forward to staying again."
United States
Julie S.
The price is £200
includes taxes & fees
5 Oct - 6 Oct
Brand New, Conveniently Located In Marion, KY
A modern kitchen with a black refrigerator, white cabinets, and a marble dining table with chairs.

19. Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!

Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!
Owensboro
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and the host was quick to answer any questions I had. My daughter had a volleyball tournament in Owensboro and the house was cheaper than a hotel! I will forever be thankful that the Lord placed this home on my options. It was beautiful and a great place to stay! 1000/10 recommend."
United States
Tyler C.
The price is £312
includes taxes & fees
12 Oct - 13 Oct
Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!
A modern living room with a grey sofa, a coffee table, and a dining area with wooden chairs and a table.

20. 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 £264
includes taxes & fees
5 Oct - 6 Oct
4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World
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 Webster County Hotel Reviews

Envi Boutique Hotel

Envi Boutique Hotel

10/10 Excellent
"Everything was GREAT!!!!!!!"
Christopher 1-night trip
Posted 14 hours ago
Envi Boutique Hotel

Find out more about Webster County

Holiday Apartments in Webster County

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