Lodging Image

Webster County Vacation 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 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 CA $107
CA $518 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $127
CA $532 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $180
CA $285 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $157
CA $238 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $141
CA $217 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $121
CA $234 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.
A bathroom with a white vanity, a toilet, a shower with a glass door, and a mirror above the vanity.

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 CA $205
CA $372 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $132
CA $414 total
includes taxes & fees
Oct 28 - Oct 29
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 CA $178
CA $420 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $305
CA $523 total
includes taxes & fees
Oct 25 - Oct 26
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 CA $141
CA $283 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $187
CA $334 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $232
CA $465 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $212
CA $308 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $192
CA $410 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $229
CA $552 total
includes taxes & fees
Oct 8 - Oct 9
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 CA $160
CA $430 total
includes taxes & fees
Oct 6 - Oct 7
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 CA $205
CA $372 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $211
CA $589 total
includes taxes & fees
Oct 12 - Oct 13
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 CA $207
CA $498 total
includes taxes & fees
Oct 5 - Oct 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Webster County Hotel Reviews

Baymont by Wyndham Madisonville

Baymont by Wyndham Madisonville

8/10 Good
"Clean & nice breakfast. Should have requested 1st floor room rather than 2nd floor which had some late night noise."
Patti-Joy 1-night trip
Posted 7 hours ago
Baymont by Wyndham Madisonville

Find out more about Webster County

Everything you need to know about Webster County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Webster County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Webster County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Webster County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Webster County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Webster County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Webster County vacation rentals we have selected for you start as low as CA $217 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Webster County rentals

At Expedia, we put the best Webster County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Webster County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Webster County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Webster County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.