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Webster County Vacation Rentals

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Our top choices for Webster County vacation rentals

A spacious living room with hardwood floors, a wooden coffee table, a sofa, and a chandelier.

1. Littlefield Farmhouse in Princeton, KY

Littlefield Farmhouse in Princeton, KY
Princeton
10.0 out of 10, Exceptional, (45 reviews)
"Wonderful place to stay!"
United States
Beverly W.
The price is CA $196
CA $310 total
includes taxes & fees
Nov 20 - Nov 21
Littlefield Farmhouse in Princeton, KY
A bathroom with a vanity, a mirror, a sink, a towel rack, and a window with a view of a garden.

2. Union Station Union Station

Union Station Union Station
Madisonville
9.4 out of 10, Exceptional, (6 reviews)
"Was a beautiful house and a lovey stay! "
United States
Rhonda P.
The price is CA $129
CA $430 total
includes taxes & fees
Nov 5 - Nov 6
Union Station Union Station
An open-plan living area with a sofa, two armchairs, a ceiling fan, and a door leading to a balcony.

3. 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 $125
CA $496 total
includes taxes & fees
Nov 8 - Nov 9
Loop Haven is an awesome place to stay.
A wooden observation tower with a small deck and stairs, surrounded by trees.

4. Charming Treehouse with Lake View and Access

Charming Treehouse with Lake View and Access
Utica
9.8 out of 10, Exceptional, (127 reviews)
"Awesome place to have some time with family away from everyone."
United States
Lori
The price is CA $145
CA $209 total
includes taxes & fees
Nov 5 - Nov 6
Charming Treehouse with Lake View and Access
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

5. 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 $201
CA $350 total
includes taxes & fees
Nov 6 - Nov 7
Brand New, Conveniently Located In Marion, KY
A room with wooden paneling, a brown leather sofa, and a door leading to another room.

6. The Nisbet Nest The Nisbet Nest

The Nisbet Nest The Nisbet Nest
Madisonville
6.0 out of 10, (1 review)
The price is CA $174
CA $523 total
includes taxes & fees
Nov 17 - Nov 18
The Nisbet Nest The Nisbet Nest
A kitchen with a wooden countertop, a stove, and a refrigerator.

7. Sweet Dreams in Sacramento

Sweet Dreams in Sacramento
Sacramento
8.4 out of 10, Very good, (6 reviews)
"This the second time that we have stayed at this location for the Civil War reenactment "
United States
Paul R.
The price is CA $112
CA $332 total
includes taxes & fees
Nov 8 - Nov 9
Sweet Dreams in Sacramento
A spacious kitchen with a central island, wooden cabinets, and a ceiling fan.

8. 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, (4 reviews)
"Cozy and clean home that had all of the little things we needed! Easy access to all of the cool hiking spots in the area!"
United States
Lisa L.
The price is CA $128
CA $228 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.
A blue triangular building with a porch, two chairs, and a gravel driveway.

9. 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, (7 reviews)
"Great quiet location! It was very clean and comfy! Will definitely be back again!!"
United States
Deborah K
The price is CA $251
CA $413 total
includes taxes & fees
Dec 1 - Dec 2
The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit
A kitchen with wooden cabinets, a stove, and a dining area with a table and chairs.

10. 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, (4 reviews)
"I had a very easy and amazing experience with our party of 7 here."
United States
Mustafa
The price is CA $180
CA $309 total
includes taxes & fees
Nov 5 - Nov 6
Rustic 1 bedroom/1 bath home w/loft that sleeps 8. Near Shawnee National Forest
A two-story house with a porch, a front door, and a small front yard.

11. Beautiful Southern Home

Beautiful Southern Home
Sacramento
9.2 out of 10, Wonderful, (5 reviews)
"The host was accommodating, and the house was conveniently located near everything we needed it to be!"
United States
Courtney W.
The price is CA $113
CA $536 total
includes taxes & fees
Nov 5 - Nov 6
Beautiful Southern Home
A rustic cabin with a stone foundation, wooden siding, and a covered porch.

12. 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, (10 reviews)
"Super secluded and special place to unwind and disconnect. We really enjoyed the proximity to Owensboro. The hosts were very friendly and helpful during our stay and made us feel at home. Furnishings were all very comfortable. Lots of room to roam and enjoy."
United States
James A.
The price is CA $178
CA $406 total
includes taxes & fees
Dec 5 - Dec 6
Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro
A modern living room with a dining table, chairs, a sofa, and a television.

13. Bluegrass Nest- Sleeps 8

Bluegrass Nest- Sleeps 8
Owensboro
The price is CA $197
CA $444 total
includes taxes & fees
Nov 5 - Nov 6
Bluegrass Nest- Sleeps 8
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!

Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
Owensboro
9.8 out of 10, Exceptional, (37 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 $151
CA $280 total
includes taxes & fees
Nov 5 - Nov 6
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
A modern living room with a flat-screen TV, a fireplace, a dining area, and a kitchen with bar stools.

15. Bluegrass Loft | Hot Tub & Fenced Patio

Bluegrass Loft | Hot Tub & Fenced Patio
Owensboro
The price is CA $211
CA $438 total
includes taxes & fees
Nov 8 - Nov 9
Bluegrass Loft | Hot Tub & Fenced Patio
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 $125
CA $392 total
includes taxes & fees
Nov 10 - Nov 11
The Bluegrass Barbie
A modern kitchen with a white countertop, a stainless steel sink, and grey cabinets.

17. 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 $256
CA $557 total
includes taxes & fees
Nov 8 - Nov 9
The Mint Julep! Upstairs 3BD 2BA Next to Brewery
A modern kitchen with white cabinets, a wooden island, and a gray sofa with yellow pillows.

18. Lake Country House on City Square

Lake Country House on City Square
Princeton
9.8 out of 10, Exceptional, (30 reviews)
"Our stay was excellent and even better we were close to family so we didn't need to travel far after activities."
United States
Stacey S.
The price is CA $189
CA $385 total
includes taxes & fees
Nov 12 - Nov 13
Lake Country House on City Square
A house with a porch, surrounded by trees and a sign that reads 'The Duval House'.

19. Quiet 3-bedroom house in Mexico, Kentucky

Quiet 3-bedroom house in Mexico, Kentucky
Marion
10.0 out of 10, Exceptional, (13 reviews)
"Great convenient stay close to family!"
United States
Andrew W.
The price is CA $222
CA $446 total
includes taxes & fees
Nov 5 - Nov 6
Quiet 3-bedroom house in Mexico, Kentucky
A modern kitchen with white cabinets, a built-in refrigerator, and a dining area with a marble table and chairs.

20. 3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown

3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown
Owensboro
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful time here. The home was easy to check in to and the host was very responsive."
United States
Isaac D.
The price is CA $157
CA $424 total
includes taxes & fees
Nov 15 - Nov 16
3BR Owensboro Home- Fenced Yard- Pet Friendly- Near KWC & Downtown
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

Greenfield Inn & Suites Owensboro, KY Airport

Greenfield Inn & Suites Owensboro, KY Airport

10/10 Excellent
"This place was great! It fit our needs properly."
Tracey 1-night trip
Posted 6 hours ago
Greenfield Inn & Suites Owensboro, KY Airport

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 $209 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.