Winona Vacations from $254
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Your Winona Vacation
Entertainment, history, art and more … There's a whole lot to discover with a Winona vacation package. And with the ability to easily customize your city adventure, it's guaranteed to be one to remember. A trip to Winona wouldn't be complete without swinging by some popular attractions, like Tiger Creek Wildlife Refuge. Your ideal Winona vacation is just clicks away. Explore airfares, hotels and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Winona vacation packages
Price found within the past 48 hours. Click for updated prices.
Executive Inn
$254
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
St. Louis (STL) to Longview (GGG)
6.8/10 (161 reviews)
In the shower were dirty towels that had been left from who knows how long. After leaving we were charged an extra fee for “stolen blankets”. We stripped the beds and left all blankets on the floor. No blankets were stolen. This place is a complete scam and I would strongly suggest you stay away.
Reviewed on Sep 20, 2026
Greyhound Inn
$354
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
St. Louis (STL) to Tyler (TYR)
9.8/10 Exceptional! (83 reviews)
Unique property.
The large empty lobby already feels "full" of past travelers in period outfits.
The room was spacious and comfortable.
Personally, I should've brought my pillow(s). They didn't work for me--too large and flattened.
I can't speak to the area... unusual downtown spot. But I was simply attracted to the uniqueness
Reviewed on Sep 19, 2026
Stay near popular Winona attractions
Mrs. Lee's Daffodil Garden
5.4/10 (3 reviews)
Explore the great outdoors at Mrs. Lee's Daffodil Garden, a lovely green space in Winona.
Winona Hotel Deals
Nexstay Grand Hotel & Conference Center
3310 Troup Hwy Tyler TX
Fully refundableReserve now, pay when you stay
$44 nightly
$51 total
Oct 5 - Oct 6
Total with taxes and fees
7.2/10 Good! (85 reviews)
"Room was not clean. The beds were made but that’s it. Stuff on the walls, cob webs, floors dirty. One of the lamps didn’t work and we called to let them know, said they’d send someone but never did. It was the one with all the plug ins so was essential. At check in the guy told us the room number ..."
Reviewed on Oct 4, 2026
Sleep Inn & Suites Tyler South
5555 Donnybrook Avenue Tyler TX
Fully refundable
$67 nightly
$77 total
Nov 1 - Nov 2
Total with taxes and fees
Contessa Inn
717 S Hwy 31 Longview TX
Fully refundableReserve now, pay when you stay
$36 nightly
$41 total
Oct 6 - Oct 7
Total with taxes and fees
8.4/10 Very Good! (446 reviews)
"Good to start over and be somewhat ok"
Reviewed on Oct 4, 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 Winona Vacation Packages
Winona Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Pounds Regional Airport (TYR) |
Population | 600 |
Max Temp Winter | 55ºF |
Max Temp Summer | 95ºF |
Top Sights | Tyler State Park, Caldwell Zoo and Liberty Hall |
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Frequently asked questions
How much does a Winona vacation package cost?
You can grab a vacation package to this destination from $254 on Expedia. But how much your vacation to Winona costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Winona?
January, October and December are great times to look for cheap Winona vacation packages. Opting to travel in quieter periods means you can typically find lower prices on accommodations and flights.
How many days is enough for Winona?
With a well-organized itinerary, you can easily visit the main Winona attractions in a handful of days. But if you prefer to discover hidden gems or take day trips, think about booking your Winona vacation for longer.
How to find the best Winona package deals?
Landing a cheap Winona package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Winona package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Winona vacation as a package?
You can enjoy significant savings on your Winona getaway by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Winona?
If you're planning a spur-of-the-moment Winona trip, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Winona vacation packages?
Your Winona getaway is meant to be a relaxing escape from your daily routine, not a reason for money worries. So to give you extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
