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Winona Vacations from $597

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The Latest Winona Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby sitting area
    Aug 28 - Aug 31

    OYO Hotel Tyler Lindale + Flight

    Tyler
    3 nights
    2.0 star property
    7.2/10 - Good (147 reviews)
    "This is complety a scam, the pool is disgusting ,theres no breakfast or even a gym, This whole establishment is falling apart, I open the fridge and there was a roach ,I Will never ever stay here again"
    Reviewed July 24, 2026
    Roundtrip • Fort Lauderdale (FLL) - Tyler (TYR)
    FLL - TYR • 1 stop TYR - FLL • 1 stop
    $625
    $597
    per traveler
    found 21 hours ago
    OYO Hotel Tyler Lindale
  • Panoramic Suite | 1 bedroom, in-room safe, desk, laptop workspace
    Aug 28 - Aug 31

    Greyhound Inn + Flight

    Tyler
    3 nights
    2.0 star property
    9.6/10 - Exceptional (72 reviews)
    Roundtrip • Fort Lauderdale (FLL) - Tyler (TYR)
    FLL - TYR • 1 stop TYR - FLL • 1 stop
    $796
    $720
    per traveler
    found 21 hours ago
    Greyhound Inn
  • Desk, WiFi (free), bed sheets
    Aug 28 - Aug 31

    Motel 6 Tyler, TX + Flight

    Tyler
    3 nights
    2.0 star property
    8.6/10 - Excellent (623 reviews)
    Roundtrip • Fort Lauderdale (FLL) - Tyler (TYR)
    FLL - TYR • 1 stop TYR - FLL • 1 stop
    $684
    $641
    per traveler
    found 21 hours ago
    Motel 6 Tyler, TX
  • Premium bedding, pillowtop beds, desk, iron/ironing board
    Aug 28 - Aug 31

    Sleep Inn & Suites Tyler South + Flight

    Tyler
    3 nights
    2.5 star property
    9.4/10 - Exceptional (1,022 reviews)
    "I have stayed at this property for years every time I make a trip to Tyler. The staff is courteous and professional and goes out of their way to be helpful. Everyone I have encountered seems very customer-focused. I highly recommend this property when in Tyler."
    Reviewed July 27, 2026
    Roundtrip • Fort Lauderdale (FLL) - Tyler (TYR)
    FLL - TYR • 1 stop TYR - FLL • 1 stop
    $685
    $648
    per traveler
    found 21 hours ago
    Sleep Inn & Suites Tyler South
  • Bar (on property)
    Aug 28 - Aug 31

    The Thomas Hotel + Flight

    Tyler
    3 nights
    2.0 star property
    9.4/10 - Exceptional (127 reviews)
    "Our only complaint, the bed sheets were stained. That being said, Michelle, the wonderful woman running the place at the time, quickly brought fresh sheets to the room. The room\ was very spacious and set up well. We loved the downstairs bar and the cocktails were very good. All in all, we would gladly stay here again."
    Reviewed July 21, 2026
    Roundtrip • Fort Lauderdale (FLL) - Tyler (TYR)
    FLL - TYR • 1 stop TYR - FLL • 1 stop
    $830
    $789
    per traveler
    found 21 hours ago
    The Thomas Hotel

Winona Hotel Deals

Lobby

Country Side Inn

Country Side Inn
2.0 star property
3.1 mi from Winona
5.8 out of 10, (17 reviews)
"I don’t even know what to say about this hotel. I guess when I reserved a room for $59 in Tyler, Texas I should have known what to expect. The lobby that is shown in the pictures on Expedia doesn’t exist. You walk into this tiny little storage room with old unplugged, broken vending machines and you have to go up to a window to slide your ID and credit card in. The door does not have the extra top lock latch. The room was not fully supplied with towels. There were spiderwebs everywhere, stains...
$62 nightly
The price is $66
Jul 31 - Aug 1
Total with taxes and fees
Country Side Inn
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.
See all properties in Winona

Frequently Asked Questions

How much does a Winona vacation package cost?

You can grab a vacation package to this destination from $597 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.