Webster County Holiday Rentals

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Top Holiday Rentals Destinations in Webster County

Over Yonder!!
Terrace/patio

Over Yonder!!

10.0 out of 10, Exceptional, (5)
"Over Yonder is surrounded by beautiful property. The cabin is so cozy and decorated beautifully. We had four people in our group and we were all comfortable. The outside sitting area and fireplace was set up with all items need for relaxation and enjoyment. The host was very informative and answered any questions promptly. We would definitely stay here again."
Over Yonder!!
VALLEY VIEW LODGE, A MODERN CABIN IN WESTERN KY
Exterior

VALLEY VIEW LODGE, A MODERN CABIN IN WESTERN KY

10.0 out of 10, Exceptional, (26)
"Wonderful location to stay. Hosts were very accommodating and when we had an issue with the AC they arranged plans to fix it immediately! "
VALLEY VIEW LODGE, A MODERN CABIN IN WESTERN KY
Private Lake & Dock: Log Cabin, 2 Mi to Clay!
House (1 Bedroom) | Interior

Private Lake & Dock: Log Cabin, 2 Mi to Clay!

2.0 star property
Private Lake & Dock: Log Cabin, 2 Mi to Clay!
Brown’s Bar countryliving Spacious 4 bedroom 3 full bath near Blackford Oaks WMA
Fridge, microwave, oven, stovetop

Brown’s Bar countryliving Spacious 4 bedroom 3 full bath near Blackford Oaks WMA

Brown’s Bar countryliving Spacious 4 bedroom 3 full bath near Blackford Oaks WMA
Charming Treehouse with Lake View and Access
Exterior

Charming Treehouse with Lake View and Access

9.6 out of 10, Exceptional, (79)
"Me and my wife really enjoyed our stay!!"
The price is NZ$268
includes taxes & fees
8 Oct - 9 Oct
Charming Treehouse with Lake View and Access
Centrally located 3 bdrm 2 bath quaint house with a yard. Pet friendly.
Interior

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

10.0 out of 10, Exceptional, (45)
"Great place to stay, great host, property was as advertised. Would definately stay there again"
Centrally located 3 bdrm 2 bath quaint house with a yard. Pet friendly.
Charming cabin with amazing views located on Toontucky Farms
Terrace/patio

Charming cabin with amazing views located on Toontucky Farms

10.0 out of 10, Exceptional, (3)
" Stayed for a week very nice place. "
The price is NZ$286
includes taxes & fees
1 Nov - 2 Nov
Charming cabin with amazing views located on Toontucky Farms
Charming 1-bedroom house with river view in Henderson.
Fridge, microwave, oven, stovetop

Charming 1-bedroom house with river view in Henderson.

10.0 out of 10, Exceptional, (4)
"Fantastic stay in an adorable bungalow. "
Charming 1-bedroom house with river view in Henderson.
Roos&Blues lake house. City park steps away. Rm for 6, king beds, pets friendly
Smart TV, books

Roos&Blues lake house. City park steps away. Rm for 6, king beds, pets friendly

10.0 out of 10, Exceptional, (17)
"We were in town to visit family and appreciate having a lovely place to stay. "
Roos&Blues lake house. City park steps away. Rm for 6, king beds, pets friendly
The Robinette House: Endless view of rolling farmland
Fridge, microwave, oven, stovetop

The Robinette House: Endless view of rolling farmland

10.0 out of 10, Exceptional, (77)
"This place was fantastic! Views are beautiful. Would recommend "
The Robinette House: Endless view of rolling farmland
Grandpa's Comfy Cottage
Exterior detail

Grandpa's Comfy Cottage

10.0 out of 10, Exceptional, (3)
"Everything we needed and close to everything else 👍"
Grandpa's Comfy Cottage
Lake Country House on City Square
Terrace/patio

Lake Country House on City Square

10.0 out of 10, Exceptional, (24)
"Our stay was excellent and even better we were close to family so we didn't need to travel far after activities."
Lake Country House on City Square
Charming 2-bedroom house with Great kitchen space in Madisonville.
Private kitchen

Charming 2-bedroom house with Great kitchen space in Madisonville.

2.0 star property
10.0 out of 10, Exceptional, (3)
"This property had everything we could possibly need and the hospitality items were such a special touch! She thought of everything to ensure we had a pleasant stay. "
Charming 2-bedroom house with Great kitchen space in Madisonville.
Loop Haven in Madisonville Ky.
Private kitchen

Loop Haven in Madisonville Ky.

2.0 star property
9.6 out of 10, Exceptional, (8)
"Clean, quiet and economical home! Thanks for a great stay in Madisonville!"
The price is NZ$688
includes taxes & fees
14 Oct - 15 Oct
Loop Haven in Madisonville Ky.
Brand new, conveniently located 2 bedroom apartment in Marion, KY
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (15)
"We enjoyed our stay and the apartment was super clean and accommodating "
The price is NZ$446
includes taxes & fees
8 Oct - 9 Oct
Brand new, conveniently located 2 bedroom apartment in Marion, KY
Spacious home with basement. City park steps away. Cleaning fee included.
Outdoor dining

Spacious home with basement. City park steps away. Cleaning fee included.

10.0 out of 10, Exceptional, (13)
"We love the location of this property. The Madisonville City Park has so much to offer families. We will definitely be back! Waking up in the morning and looking at the lake is a real bonus!"
Spacious home with basement. City park steps away. Cleaning fee included.
Lakeside Log Cabin-Wedding Venue -Hunting -Fishing
Outdoor dining

Lakeside Log Cabin-Wedding Venue -Hunting -Fishing

10.0 out of 10, Exceptional, (31)
"Amazing property if you have a larger family and need the beds and bathrooms. Lots of gathering space and deck space. Well-equipped and far enough out to feel like a getaway in itself. Thanks for everything!"
Lakeside Log Cabin-Wedding Venue -Hunting -Fishing
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (22)
"My nephew and I really enjoyed our one night stay in this lovely little house. Randy was here to meet us when we checked in and showed us around when we come down again next year we will be sure to contact him."
The price is NZ$350
includes taxes & fees
8 Oct - 9 Oct
Uniquely remodeled 3 bdrm 1 bth home in safe area! Fenced in with a large deck!
Newly renovated- 2.5 mi to Downtown Riverfront
Fridge, microwave, oven, stovetop

Newly renovated- 2.5 mi to Downtown Riverfront

10.0 out of 10, Exceptional, (16)
"We had an excellent stay at Jennifer’s home. Would love to stay here again."
Newly renovated- 2.5 mi to Downtown Riverfront
Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (1)
"Property as described rustic with all modern amenities plenty of room yet cozy and warm atmosphere. Kevin our host was great and left us feeling like family. Highly recommend this little Gem. Can’t wait to return this fall. "
The price is NZ$494
includes taxes & fees
8 Oct - 9 Oct
Rustic 1800s' Log Cabin with Modern Amenities on an Old Farm close to Owensboro
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
"Very clean and great staff"
Keith 2-night trip
Posted 4 days ago
Greenfield Inn & Suites Owensboro, KY Airport

Find out more about Webster County

Find out more about Webster County

Everything you need to know about Webster County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Webster County holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Webster County holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Webster County holiday rentals we have selected for you start as low as NZ$268 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 holiday 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 holiday.

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.