Webster County Vacation Packages

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Your Webster County Vacation

Make planning your next getaway a piece of cake with a Webster County vacation package. Whether it's nature, history or something else that lures you to this destination, our package deals will help you discover the best of it. Can't decide where to stay? Clay is one of the best cities to visit during a trip to Webster County. Round up your loved ones and pack your bags, because your Webster County vacation is only a few clicks away with Expedia.

Top Webster County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Envi Boutique Hotel Henderson-Evansville South

Envi Boutique Hotel Henderson-Evansville South

3 out of 5
Price was CA $1,409, price is now CA $1,219 per person
CA $1,219
per person
Jun 16 - Jun 22
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
8/10 Very Good! (302 reviews)
Very clean and elegant would highly recommend even for a weekend getaway perfect !!!

Reviewed on Apr 19, 2026

Fairfield Inn By Marriott Evansville East

Fairfield Inn By Marriott Evansville East

3 out of 5
Price was CA $1,408, price is now CA $1,246 per person
CA $1,246
per person
Jun 16 - Jun 22
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
8.6/10 Excellent! (490 reviews)
Very nice property. I have stayed here before and will return. Great staff. Breakfast is fresh but don’t care for turkey sausage.

Reviewed on Apr 18, 2026

Residence Inn by Marriott Evansville East

Residence Inn by Marriott Evansville East

3 out of 5
Price was CA $1,445, price is now CA $1,283 per person
CA $1,283
per person
Jun 16 - Jun 22
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
8.6/10 Excellent! (532 reviews)
The staff was and has always been phenomenal. Great rooms. And a great price. Mo and Tara were extremely kind and helpful. This was my 2nd time staying there and was completely impressed the first time.

Reviewed on Apr 27, 2026

Comfort Inn Evansville East

Comfort Inn Evansville East

2.5 out of 5
Price was CA $1,389, price is now CA $1,257 per person
CA $1,257
per person
Jun 16 - Jun 22
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
7.8/10 Good! (859 reviews)
Coffee pot was broken

Reviewed on Apr 21, 2026

Spark by Hilton Evansville Downtown

Spark by Hilton Evansville Downtown

2.5 out of 5
Price was CA $1,375, price is now CA $1,247 per person
CA $1,247
per person
Jun 16 - Jun 22
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Evansville (EVV)
8.4/10 Very Good! (6 reviews)
It was not walking distance to venue as stated. Kinda sketchy side of town, but people were great and room was nice and clean. Breakfast bar was really lacking.

Reviewed on Apr 3, 2026

Webster County Hotel Deals

Over Yonder!!

Over Yonder!!

Sebree KY
10/10 Exceptional! (10 reviews)
Just a great outing. Cabin was warm and the fire pit was great. Enjoyed a big fire both nights and watched some good movies on the DVR. The bathroom and shower area are very large for a small cabin. Great place to catch up with old friends and talk the night away. 5 star for sure. The host was quick ...

Reviewed on Feb 22, 2026

Get rates
Over Yonder!!
Greenfield Inn & Suites Owensboro, KY Airport

Greenfield Inn & Suites Owensboro, KY Airport

2.5 out of 5
3220 W Parrish Ave Owensboro KY
Fully refundableReserve now, pay when you stay
The price is CA $105 per night from May 12 to May 13
CA $105
CA $119 total
May 12 - May 13
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Breakfast was good, room was clean

Reviewed on Apr 28, 2026

Greenfield Inn & Suites Owensboro, KY Airport
Days Inn by Wyndham Madisonville

Days Inn by Wyndham Madisonville

2 out of 5
1900 Lantaff Blvd Madisonville KY
Fully refundableReserve now, pay when you stay
The price is CA $111 per night from May 3 to May 4
CA $111
CA $123 total
May 3 - May 4
includes taxes & fees
7/10 Good! (908 reviews)
Nice, friendly, clean, and you felt safe.

Reviewed on Apr 29, 2026

Days Inn by Wyndham Madisonville
See all 130 properties in Webster County
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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Webster County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Webster County from just CA $1,219. And the more you bundle, the more you save. Your dream vacation has never been so affordable.
How do I get a cheap travel package to Webster County?
Search for flights that fit your busy schedule, add a hotel to your booking and watch how much you save with a Webster County vacation package. It's that simple! From flights and hotels to activities and rental cars, Expedia makes traveling cheaply a cinch. And with more than 550 partner airlines and 1,000,000 hotel options worldwide to select from, you'll never be short of choice.
How far in advance should I book my Webster County vacation?
It all depends on the air carrier, but it's usually possible to compare international flights on Expedia up to a year in advance. While it's generally a good idea to book ahead of time, lucky travelers will sometimes score a cheaper seat just weeks before departure dates.
What does an Expedia Webster County travel package include?
Flights, hotels and a cool set of wheels for all your fun road trip adventures. Simply mix and match your favorite bundle and get access to incredible deals. Once you've made your booking, add on some tours and experiences and watch your savings grow. When it comes to creating your Webster County getaway, you're the one in control!
What should I know before booking a Webster County travel package?
So many places to venture to, so many things to experience. With a package, you'll be able to cross more of them off your list. Bundle your flights, hotels and rental cars and land big savings.
Can I choose my airline with a Webster County Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our packages give you the flexibility to pick from available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Webster County vacation package?
Yes you can, and we're here to help. You may be able to cancel or change your Webster County vacation package for free within 24 hours of booking. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If your circumstances suddenly change, visit our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.