Winston Vacations from $252
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Winston vacation packages
Price found within the past 48 hours. Click for updated prices.
Best Western Plus KC Speedway Inn & Suites
I-435 West
$252
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip flight included
Denver (DEN) to Kansas City (MCI)
7/10 Good! (1,002 reviews)
Great stay, everyone very pleasant and treaty my granddaughters wonderful, did not ignore them, but talk to them!
Everything very clean, but not chemical smell
Great stay
Reviewed on Aug 22, 2026
Isle of Capri Casino Hotel Boonville & Casino - A Caesars Rewards Destination
$604
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Kansas City (MCI)
8.4/10 Very Good! (1,021 reviews)
The room was very clean! The staff was very friendly and helpful! The casino was clean, the staff was friendly, and the bar staff was very helpful and supper nice!
Reviewed on Aug 23, 2026
Winston Hotel Deals
SureStay Hotel by Best Western Cameron
2210 US Highway 36 Cameron MO
Fully refundableReserve now, pay when you stay
$78 nightly
$86 total
Aug 30 - Aug 31
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"What wasn't moldy was rusty. The pillows were awful. The AC rumbled and clanged all night. It's a shame the property isn't kept up because it could be really nice. The outside is like a big beautiful park! The staff was great, except the son of the owner who couldn't control his off-leash dog. The ..."
Reviewed on Aug 21, 2026
Red Roof Inn Cameron
501 Northland Drive Cameron MO
Fully refundableReserve now, pay when you stay
$88 nightly
$96 total
Sep 3 - Sep 4
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
"Nice room spacious location was good as well."
Reviewed on Aug 23, 2026
Quality Inn Cameron
1803 Comfort Ln Cameron MO
Fully refundable
$114 nightly
$127 total
Sep 23 - Sep 24
Total with taxes and fees
8.6/10 Excellent! (701 reviews)
"Very efficient stay. Easy in and out. Clean and safe"
Reviewed on Aug 22, 2026
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.
Find the Best Winston Vacation Packages
Winston Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | Gallatin Methodist Church, Cameron Veterans Memorial Golf Glub and Adam-ondi-Ahman |
More vacations you might like
Frequently asked questions
How much does a Winston vacation package cost?
You'll find cheap prices from $252 on Expedia for your Winston break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Winston costs.
What are the cheapest months to go to Winston?
If you'd like to score a cheap Winston vacation package, consider planning a trip in December, January and February. You're likely to find lower prices on accommodations and flights during these months — ideal for budget-conscious travelers.
How many days is enough for Winston?
Typically, a handful of days is enough to check out the major sights during your Winston vacation. But if you prefer to have some time to chill out or take day tours, think about extending your itinerary.
How to find the best Winston package deals?
Bagging a cheap Winston package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can customize your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Winston package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winston vacation as a package?
You can enjoy significant savings on your Winston getaway by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winston?
If you're planning a spur-of-the-moment Winston trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Winston vacation packages?
Set off on your dream trip to Winston with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next payday — we've teamed up with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans let you spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
