Winona Vacations from $538

Book a Hotel + Flight or Car together to unlock savings

Photo by Kirsten

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Hotel Indigo Rochester – Mayo Clinic Area by IHG

Hotel Indigo Rochester – Mayo Clinic Area by IHG

3.5 out of 5
Downtown Rochester
Price was $629, price is now $538 per person
$538
per person
Jan 20 - Jan 23
found 20 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rochester (RST)
8.8/10 Excellent! (867 reviews)
The room was nice, staff were friendly and the skyway to the Civic Center was great & very convenient! Would stay here again!

Reviewed on Dec 17, 2025

Americas Best Value Inn Zumbrota

Americas Best Value Inn Zumbrota

2 out of 5
Price was $1,263, price is now $1,073 per person
$1,073
per person
Jan 20 - Jan 23
found 18 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rochester (RST)
7.2/10 Good! (502 reviews)
Quiet pretty decent

Reviewed on Dec 6, 2025

The Berkman

The Berkman

3 out of 5
Folwell
Price was $741, price is now $639 per person
$639
per person
Jan 20 - Jan 23
found 20 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rochester (RST)
9.6/10 Exceptional! (363 reviews)
Staff was great, as was the room.

Reviewed on Dec 8, 2025

Aspen Select

Aspen Select

3.5 out of 5
Price was $693, price is now $610 per person
$610
per person
Jan 20 - Jan 23
found 18 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rochester (RST)
8.4/10 Very Good! (1,003 reviews)
Staff at the front desk was very curtious and helpful with directions. Loved the smell and taste of the warm cookies.

Reviewed on Dec 17, 2025

Kahler Inn and Suites - Mayo Clinic Area

Kahler Inn and Suites - Mayo Clinic Area

3.5 out of 5
Downtown Rochester
Price was $846, price is now $748 per person
$748
per person
Jan 20 - Jan 23
found 18 hours ago
Roundtrip non-stop flight included
Des Moines (DSM) to Rochester (RST)
8/10 Very Good! (1,495 reviews)
Clean rooms & public areas in a great location , friendly staff, comfortable beds, nice breakfast choice connected to lower level sub walk to all Mayo bldgs & several bars /eateries.

Reviewed on Dec 12, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winona
View all trips

Discover the most popular places to visit in Winona

Winona State University

Winona State University

4.5/5(94 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
Sugarloaf trail....360 degree views from the top of sugar loaf of the Mississippi River valley. 28 routes for rock climbing to the peak....nice hiking trail to the base!

Sugar Loaf

4/5(62 reviews)

Explore the great outdoors at Sugar Loaf, a lovely green space in Winona. Stroll along the riverfront or experience the area's museums.

Sugar Loaf
The old mill is also available for tours

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

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
$110 nightly
The price is $123 total per night from Dec 21 to Dec 22
$123 total
Dec 21 - Dec 22
Total with taxes and fees
8.4/10 Very Good! (1,001 reviews)
Room was clean and well prepared. Guest service members were very pleasant and nice. Overall, a nice stay.

Reviewed on Dec 2, 2025

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
$100 nightly
The price is $112 total per night from Dec 28 to Dec 29
$112 total
Dec 28 - Dec 29
Total with taxes and fees
9/10 Wonderful! (892 reviews)
Place looks brand new, staff was awesome, pool and hot tub in perfect working order and clean, small bar was pleasant to watch a game and grab beer or wine, quiet hotel, comfortable beds and an electric reclining chair, small kitchenette, and breakfast was above average with bacon, eggs, and pancakes. ...

Reviewed on Dec 7, 2025

AmericInn by Wyndham Winona
Holiday Inn Express & Suites Winona by IHG

Holiday Inn Express & Suites Winona by IHG

2.5 out of 5
1128 Homer Rd Winona MN
Fully refundable
$123 nightly
The price is $137 total per night from Jan 4 to Jan 5
$137 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (896 reviews)
The only thing we didn't care for was breakfast. Some items were cold. The attendent was very nice. Overall, an excellent stay. Would stay again.

Reviewed on Dec 1, 2025

Holiday Inn Express & Suites Winona by IHG
See all 344 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winona vacation package cost?
Offering excellent value package deals from $538 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.

Explore a world of travel with Expedia

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