Winona Vacations from $483

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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.
Economy Inn by Hotel O Gladewater, TX

Economy Inn by Hotel O Gladewater, TX

2 out of 5
Price was $586, price is now $483 per person
$483
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Longview (GGG)
7/10 Good! (24 reviews)
It was clean friendly and convenient for everything

Reviewed on Oct 7, 2024

Rose City Inn & Suites

Rose City Inn & Suites

2 out of 5
Save 100% on your flight
Price was $3,027, price is now $2,148 per person
$2,148
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Tyler (TYR)
5.8/10 (359 reviews)
The hallways had a horrendous smell but the room didn't. The property is very old but they're working on it. Value for the money.

Reviewed on Feb 26, 2026

Trade Wind Motel Jacksonville TX US 69

Trade Wind Motel Jacksonville TX US 69

2.5 out of 5
Price was $681, price is now $514 per person
$514
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Tyler (TYR)
6/10 (4 reviews)
The hotel’s placement made arrival and departure smooth. The room was tidy and calming. Staff behavior was dependable.

Reviewed on Feb 8, 2026

Motel 6 Longview, TX - North

Motel 6 Longview, TX - North

2 out of 5
Price was $574, price is now $485 per person
$485
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Longview (GGG)
8/10 Very Good! (1,003 reviews)
I was a great stay, my husband and I just go for a day to get renergized. The only problem that we had was, I had requested a downstairs room, because I have arthritis

Reviewed on Feb 25, 2026

Best Western Plus Royal Mountain Inn & Suites

Best Western Plus Royal Mountain Inn & Suites

2.5 out of 5
Price was $770, price is now $654 per person
$654
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Tyler (TYR)
9/10 Wonderful! (903 reviews)
Very friendly helpfull staff. Super clean. Many resturants with a mile.

Reviewed on Mar 2, 2026

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Discover the most popular places to visit in Winona

Mrs. Lee's Daffodil Garden

3.5/5(2 reviews)

Explore the great outdoors at Mrs. Lee's Daffodil Garden, a lovely green space in Winona.

Mrs. Lee's Daffodil Garden

Winona Hotel Deals

Tru by Hilton Longview

Tru by Hilton Longview

2.5 out of 5
3037 N. Eastman Rd. Longview TX
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $68 total per night from Mar 22 to Mar 23
$68 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (848 reviews)
The wall next to the bed is too thin. Could hear too much noise from adjacent room. Will not stay there again.

Reviewed on Mar 14, 2026

Tru by Hilton Longview
La Quinta Inn & Suites by Wyndham Tyler South

La Quinta Inn & Suites by Wyndham Tyler South

3 out of 5
6702 S Broadway Ave Tyler TX
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $94 total per night from Apr 5 to Apr 6
$94 total
Apr 5 - Apr 6
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
The staff was friendly & the check in process went quickly. The room was large, clean, & comfortable, with a large stall shower in the bathroom.

Reviewed on Mar 13, 2026

La Quinta Inn & Suites by Wyndham Tyler South
Courtyard by Marriott Tyler

Courtyard by Marriott Tyler

3 out of 5
7424 S Broadway Ave Tyler TX
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $128 total per night from Mar 21 to Mar 22
$128 total
Mar 21 - Mar 22
Total with taxes and fees
8.4/10 Very Good! (722 reviews)
na

Reviewed on Mar 12, 2026

Courtyard by Marriott Tyler
See all 541 properties in Winona
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 $483 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.