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Vacation Homes in Webster County

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Webster County vacation homes

A hot tub in a backyard with a wooden deck, outdoor furniture, and a covered patio area.

1. The Bluegrass House

The Bluegrass House
Owensboro
9.8 out of 10, Exceptional, (46 reviews)
"Had a wonderful stay with my brother and some friends while attending omg!con. Wonderful for a weekend getaway"
United States
Cheyenne M.
The Bluegrass House
A blue triangular building with a porch, two chairs, and a gravel driveway.

2. 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, (6 reviews)
"Great quiet location! It was very clean and comfy! Will definitely be back again!!"
United States
Deborah K
The price is AED 831
AED 1,393 total
includes taxes & fees
5 Nov - 6 Nov
The Shady Roost | Cozy Cabin w/ Hot Tub & Fire Pit
A spacious kitchen with a central island, wooden cabinets, and a ceiling fan.

3. 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 AED 311
AED 602 total
includes taxes & fees
14 Oct - 15 Oct
Cozy 1-bedroom house on 17 acres in Elizabethtown, IL near the Ohio River.
A living room with a fireplace, a ceiling fan, and a flat-screen TV.

4. 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 AED 397
AED 774 total
includes taxes & fees
14 Oct - 15 Oct
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
A living room with a ceiling fan, a gray sofa, a coffee table, and a white furry chair.

5. 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 AED 340
AED 1,088 total
includes taxes & fees
28 Oct - 29 Oct
The Bluegrass Barbie
A modern kitchen with a black refrigerator, white cabinets, and a marble dining table with chairs.

6. 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.
Swiftie’s Babe Cave is a Taylor-Themed 3BR Retreat Near Downtown Owensboro!
A kitchen with wooden cabinets, a stove, and a dining area with a table and chairs.

7. 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, (3 reviews)
"I had a very easy and amazing experience with our party of 7 here."
United States
Mustafa
The price is AED 476
AED 855 total
includes taxes & fees
19 Oct - 20 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.

8. 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 AED 599
AED 1,219 total
includes taxes & fees
14 Oct - 15 Oct
The Homestead House
A spacious dining area with a large wooden table and chairs, a kitchen with white cabinets, and a ceiling with wooden beams.

9. 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.
Littlefield Farmhouse in Princeton, KY
Private kitchen

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

Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB
Owensboro
The price is AED 1,014
AED 2,438 total
includes taxes & fees
25 Oct - 26 Oct
Bluegrass Maple Manor-Sleeps 20/Game Room/HOT TUB
A living room with a grey sofa, a patterned rug, a dark bean bag, and a kitchen in the background.

11. Newly renovated- 2.5 mi to Downtown Riverfront

Newly renovated- 2.5 mi to Downtown Riverfront
Owensboro
10.0 out of 10, Exceptional, (21 reviews)
"The house was fantastic for our stay and very convenient to everything."
United States
Lori C.
Newly renovated- 2.5 mi to Downtown Riverfront
A modern kitchen with white cabinets, a wooden island, and a gray sofa with yellow pillows.

12. 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 AED 496
AED 1,065 total
includes taxes & fees
14 Oct - 15 Oct
Lake Country House on City Square
A small, illuminated wooden structure with a porch, a table, and two chairs.

13. Over Yonder!!

Over Yonder!!
Sebree
10.0 out of 10, Exceptional, (13 reviews)
"This cabin was perfect for our stay. The host had everything we needed to be able to relax, let the kids play, and enjoy meals as a family despite being away from home. It was a beautiful property and we would definitely stay again!"
United States
Chelsie
Over Yonder!!
A dark wood TV stand with a flat-screen TV and a remote control.

14. 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 AED 313
AED 929 total
includes taxes & fees
11 Nov - 12 Nov
Sweet Dreams in Sacramento
A modern kitchen with white cabinets, stainless steel appliances, and a wooden island.

15. Charming 1-bedroom house with river view in Henderson.

Charming 1-bedroom house with river view in Henderson.
Henderson
10.0 out of 10, Exceptional, (22 reviews)
"Fantastic stay in an adorable bungalow. "
United States
Tim N.
Charming 1-bedroom house with river view in Henderson.
A house with a patio, string lights, and a red umbrella.

16. Centrally Located Mid Century Traditional Home

Centrally Located Mid Century Traditional Home
Owensboro
10.0 out of 10, Exceptional, (31 reviews)
"Rooms were clean and house was as advertised. Perfect for our short stay"
United States
Bryan M.
Centrally Located Mid Century Traditional Home
A kitchen with white cabinets, a white countertop, a white stool, and a refrigerator.

17. Centrally located 3 bdrm 2 bath quaint house with a yard. Pet friendly.

Centrally located 3 bdrm 2 bath quaint house with a yard. Pet friendly.
Owensboro
10.0 out of 10, Exceptional, (62 reviews)
"Excellent house with a fenced in yard. Perfect place to stay while we visited Owensboro. Would definitely come back."
United States
Drew M.
Centrally located 3 bdrm 2 bath quaint house with a yard. Pet friendly.
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

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 AED 533
AED 1,271 total
includes taxes & fees
26 Oct - 27 Oct
4bed3Bedroom near Convention Ctr, downtown, Fisher Park, 30 min to Holiday World
A modern kitchen with a dining area, featuring a kitchen island with bar stools, a fireplace, and large windows.

19. Hot tub/pool/firepit/ 3 bedroom Home center of town 2 Livingroom's sleeps 12

Hot tub/pool/firepit/ 3 bedroom Home center of town 2 Livingroom's sleeps 12
Owensboro
10.0 out of 10, Exceptional, (2 reviews)
Hot tub/pool/firepit/ 3 bedroom Home center of town 2 Livingroom's sleeps 12
Private kitchen

20. Bluegrass Bling

Bluegrass Bling
Owensboro
Bluegrass Bling
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

Super 8 by Wyndham Owensboro

Super 8 by Wyndham Owensboro

8/10 Good
"The room was clean, smelled nice, and staff was friendly, and the location was convenient for my stay. Bathroom had moldy caulking around the shower and the ceiling had a few spots. Breakfast is basic cereal, fruit, yogurt, and Dunkin Donuts."
Holly 1-night trip
Posted 1 day ago
Super 8 by Wyndham Owensboro

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