Winona Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Top hotels in Winona

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

900 Bruski Dr Winona MN
Fully refundableReserve now, pay when you stay
S$171
20 Sept - 21 Sept
includes taxes & fees
Express Suites Riverport Inn & Suites
The Plaza Hotel & Suites Winona

The Plaza Hotel & Suites Winona

1025 Highway 61 E Winona MN
Fully refundableReserve now, pay when you stay
S$234
20 Sept - 21 Sept
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"I had two separate reservations (had issues editing original & added a 2nd night thru a separate booking - exact same room type). Upon check-in, the desk clerk said we'd have to check out in the morning & check back in later in the afternoon. Not an option for football parents: check-in/out time ..."

Reviewed on 15 Sept, 2026

The Plaza Hotel & Suites Winona
Super 8 by Wyndham Winona MN

Super 8 by Wyndham Winona MN

1025 Sugar Loaf Rd Winona MN
Fully refundableReserve now, pay when you stay
S$77
4 Oct - 5 Oct
includes taxes & fees
Super 8 by Wyndham Winona MN
See all 341 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.

Stay near popular Winona attractions

A calm lake reflecting yellow and green trees, surrounded by a forested hillside.

Lake Park

9.0/10 (43 reviews)
Lake Park encircles Lake Winona with a scenic five-mile trail and diverse recreation areas. Visitors can rent kayaks at the Lake Lodge or enjoy the ADA-accessible playground "Every Child's Dream."
See properties
A river winding through a valley with a highway running alongside it.
Photo by Amy Jo Marks

Sugar Loaf Bluff

9.0/10 (193 reviews)
This striking 85-foot rock formation atop a 500-foot bluff offers panoramic views of Winona and the Mississippi River. Hikers and climbers can explore its bolted routes while experiencing Minnesota's geological heritage.
See properties
A waterfall cascading over rocks in a forested area with a wooden bridge overhead.
Photo by Jessica Jahnke

Pickwick Mill

8.4/10 (6 reviews)
This six-story stone mill from the 1850s showcases original milling machinery and an operational water wheel. Explore all floors to witness 19th-century flour production techniques preserved in their authentic setting.
See properties

Lake Lodge Recreation Center

8.0/10 (32 reviews)
Overlooking Lake Winona, this recreation centre offers year-round outdoor adventures from kayaking to ice skating. Rent well-maintained equipment and explore scenic trails for a perfect blend of activity and tranquility.
See properties

Minnesota Marine Art Museum

9.4/10 (105 reviews)
Perched on the Mississippi River, the Minnesota Marine Art Museum showcases water-inspired masterpieces by Cézanne, Monet, and van Gogh. Explore six thoughtfully curated galleries where maritime heritage meets fine art.
See properties

Cedar Valley Golf Course

7.4/10 (13 reviews)
Nestled in Winona's bluffs, Cedar Valley Golf Course offers 27 holes across three distinct courses with rolling terrain. Enjoy a round followed by relaxation at the After Par Pub & Grill.
See properties

Winona County Historical Society

8.2/10 (37 reviews)
Housed in the historic 1915 National Guard Armoury, this centre showcases Winona County's rich past through three floors of exhibits. Browse unique local history publications in the museum shop.
See properties

Winona Public Library

After visiting Winona Public Library, make a plan to see the other sights and activities in Winona. Discover the area's live music and spas.
See properties

Frequently asked questions

How much does a Winona holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Winona costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Winona?
If you're hoping to snag a cheap Winona holiday package, consider travelling in December, January and February. You'll generally find better prices on flights and accommodation during these months — perfect for a budget-friendly getaway.
How many days is enough for Winona?
With a well-planned schedule, you can easily hit the main Winona attractions in a few days. But if you prefer to explore off the beaten track or go on day tours, think about booking your Winona holiday for longer.
Is it worth booking a holiday package to Winona?
Winona offers everything you need for an amazing getaway. Get your Winona holiday off to a flying start by visiting major attractions like Lake Park.
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 holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging accommodation 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 holiday 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.
How to plan a trip to Winona?
  1. Choose your travel dates: What you plan to do in Winona and your preferred season can help you decide when to travel.
  2. Plan your budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may arise during your trip to Winona.
  3. Decide how long to go for: Now that you know more about Winona, you can figure out the perfect length of your holiday. Pull together a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Winona holiday package that brings all your bookings together.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.