Winona Vacations from $480

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Your Winona Vacation

Its rich history, friendly locals and spectacular views are only a few of the reasons to book a vacation package to Winona. Whatever brings you to this riverside city, you're sure to have a fantastic experience. Any trip to Winona needs a well-designed itinerary. Fill yours with major attractions such as Winona State University, St. Marys University of Minnesota and Minnesota Marine Art Museum. No matter your travel plans or budget, organizing a tailored Winona vacation is a cinch with Expedia.

The Latest Winona vacation packages

Price found within the past 48 hours. Click for updated prices.
Prairie Voyager

Prairie Voyager

2.5 out of 5
Southside
Price was $573, price is now $480 per person
$480
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to La Crosse (LSE)
8.6/10 Excellent! (128 reviews)
Great inexpensive stay.

Reviewed on Mar 25, 2026

Spark by Hilton La Crosse Onalaska

Spark by Hilton La Crosse Onalaska

2.5 out of 5
Price was $1,416, price is now $1,114 per person
$1,114
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to La Crosse (LSE)
8.6/10 Excellent! (128 reviews)
Very nice property with numerous eating and shopping establishments within walking distance. I found the room very nice, comfortable and clean. Pool was very relaxing as was the sauna. The best part was the staff! Very kind and accommodating people. I will definitely rebook in the near future. Thank you to entire staff! Richard

Reviewed on Apr 26, 2026

Microtel Inn by Wyndham Onalaska/La Crosse

Microtel Inn by Wyndham Onalaska/La Crosse

2 out of 5
Price was $964, price is now $767 per person
$767
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to La Crosse (LSE)
7.6/10 Good! (1,000 reviews)
Will be great when remodeling is finished.

Reviewed on Apr 27, 2026

Northwood Inn Prairie Du Chien

Northwood Inn Prairie Du Chien

2 out of 5
Southside
Price was $629, price is now $515 per person
$515
per person
Jun 9 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to La Crosse (LSE)
8.4/10 Very Good! (116 reviews)
Check-in was easy, the room had been updated and felt very clean. Overall a really good stay.

Reviewed on Apr 26, 2026

Pearl Street Hotel & Suites

Pearl Street Hotel & Suites

2.5 out of 5
Historic Downtown La Crosse
Save 100% on your flight
Price was $2,288, price is now $1,899 per person
$1,899
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to La Crosse (LSE)
8/10 Very Good! (443 reviews)
It was dirty and rundown.

Reviewed on Apr 16, 2026

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Discover the most popular places to visit in Winona

Pickwick Mill

Pickwick Mill

Find out about the history of Winona when you spend time at Pickwick Mill. Stroll along the riverfront or experience the area's museums.

Pickwick Mill
Sugar Loaf Bluff

Sugar Loaf Bluff

4/5(64 reviews)

Learn about the local history of Winona with a stop at Sugar Loaf Bluff. Stroll along the riverfront or experience the area's museums.

Sugar Loaf Bluff

Winona State University

4.5/5(96 reviews)

Enjoy the collegiate vibe when you visit Winona State University, during your trip to Winona. Stroll along the riverfront or experience the area's museums.

Winona State University

Winona Hotel Deals

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr Winona MN
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $112 total per night from Apr 29 to Apr 30
$112 total
Apr 29 - Apr 30
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
The room was clean. The staff was friendly and helpful. Breakfast was good.

Reviewed on Apr 28, 2026

Express Suites Riverport Inn & Suites
AmericInn by Wyndham Winona

AmericInn by Wyndham Winona

2.5 out of 5
303 Pelzer Street Winona MN
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $137 total per night from May 10 to May 11
$137 total
May 10 - May 11
Total with taxes and fees
9/10 Wonderful! (930 reviews)
Clean room and breakfast was of good quatity

Reviewed on Apr 26, 2026

AmericInn by Wyndham Winona
The Plaza Hotel & Suites Winona

The Plaza Hotel & Suites Winona

3 out of 5
1025 Highway 61 E Winona MN
Fully refundableReserve now, pay when you stay
$145 nightly
The price is $162 total per night from Apr 29 to Apr 30
$162 total
Apr 29 - Apr 30
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Older hotel but the room and pool were clean. Didn’t use the workout room or sauna. Continental Breakfast was ok. The restaurant server was friendly. Food & drinks were good.

Reviewed on Apr 27, 2026

The Plaza Hotel & Suites Winona
See all 346 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
La Crosse Municipal Airport (LSE)
Population
27,100
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Minnesota Marine Art Museum, Winona County Historical Society and Garvin Heights Vineyard

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Frequently asked questions

How much does a Winona vacation package cost?
Offering excellent value package deals from $480 on Expedia, you'll be pleasantly surprised at how much a vacation to Winona costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winona?
January, February and June are the best times to look for cheap Winona vacation packages. Choosing to travel in less busy periods means you'll typically find better prices on flights and accommodations.
How many days is enough for Winona?
With a well-organized travel plan, you can easily hit the top Winona sights in a handful of days. But if you'd like to discover hidden gems or take day trips, think about booking your Winona vacation for longer.
Is it worth booking a vacation package to Winona?
Winona offers everything you need for an unforgettable escape. Get your Winona vacation off to a flying start by exploring top attractions like Lake Lodge Recreation Center.
How to find the best Winona package deals?
Begin your search for a Winona package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Winona package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winona escape underway.
Is it cheaper to book a Winona vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging accommodations and flights separately. Better still, you can tailor your Winona getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Winona?
If you've got your Winona travel dates locked in, book early to snap up some incredible deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Winona vacation packages?
Your Winona trip is meant to be an escape from your daily routine, not a source of money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.