A stone wall with a hole, overlooking a river and a town.

Winona Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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.

Top Winona vacation deals

Price found within the past 48 hours. Click for updated prices.
  • A reception desk with a wooden finish, a glass partition, and a blue wall with climbing plants.
    Dec 11 - Dec 14

    America's Stay Inn Stewartville + Flight

    Stewartville
    3 nights
    2.5 star property
    8.0/10 - Very good (500 reviews)
    Roundtrip • Toronto (YYZ) - Rochester (RST)
    YYZ - MSP • Nonstop MSP - YYZ • 1 stop
    CA $784
    CA $758
    per traveller
    found 2 hours ago
    America's Stay Inn Stewartville
  • An outdoor seating area with a fire feature, blue cushioned chairs, and a modern building with large windows in the background.
    Dec 11 - Dec 14

    Hyatt House Rochester/Mayo Clinic Area + Flight

    Downtown Rochester
    3 nights
    3.0 star property
    9.0/10 - Wonderful (1,005 reviews)
    "Great stay."
    Reviewed November 8, 2026
    Roundtrip • Toronto (YYZ) - Rochester (RST)
    YYZ - MSP • Nonstop MSP - YYZ • 1 stop
    CA $953
    CA $900
    per traveller
    found 2 hours ago
    Hyatt House Rochester/Mayo Clinic Area
  • A swimming pool with a glass ceiling, a neon sign for the KAFFLER HOTEL, and a view of the city skyline at dusk.
    Dec 11 - Dec 14

    Kahler Grand Hotel + Flight

    Downtown Rochester
    3 nights
    3.0 star property
    8.4/10 - Very good (2,407 reviews)
    "Always enjoy my stay at the Kahler Grand! You can’t get a better location for Mayo Clinic appointments, shopping, terrific restaurants and friendly staff."
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Rochester (RST)
    YYZ - MSP • Nonstop MSP - YYZ • 1 stop
    CA $1,008
    CA $954
    per traveller
    found 2 hours ago
    Kahler Grand Hotel
  • A hotel room with two beds, a large landscape painting above the headboard, a bedside table with a phone, and a blue patterned rug.
    Dec 11 - Dec 14

    Days Inn by Wyndham Winona + Flight

    Winona
    3 nights
    2.0 star property
    7.6/10 - Good (1,001 reviews)
    "Smoking smell in the room. First thing I see as I walk in is a roach on the floor. The bath tub also had a roach, once I washed that down the drain ants started to crawl out of the drain. Several more roaches were found during my stay."
    Reviewed November 5, 2026
    Roundtrip • Toronto (YYZ) - Rochester (RST)
    YYZ - MSP • Nonstop MSP - YYZ • 1 stop
    CA $844
    CA $802
    per traveller
    found 2 hours ago
    Days Inn by Wyndham Winona
  • A hotel room with two beds, green walls, and two large landscape paintings.
    Dec 11 - Dec 14

    Super 8 by Wyndham Fairmont + Flight

    Fairmont
    3 nights
    2.0 star property
    7.8/10 - Good (496 reviews)
    Roundtrip • Toronto (YYZ) - Rochester (RST)
    YYZ - MSP • Nonstop MSP - YYZ • 1 stop
    CA $812
    CA $782
    per traveller
    found 2 hours ago
    Super 8 by Wyndham Fairmont

Where to stay in Winona

Find the best Winona areas and neighborhoods for the activities you enjoy most.
A cafe interior with a wooden clock, hanging lights, and a counter with various items.
Photo by Jessica Purdue Rep
Open Photo by Jessica Purdue Rep

Historic Downtown Winona

You'll enjoy the live music and spas in Historic Downtown Winona. You might want to make time for a stop at Mississippi River or Winona County Historical Society.

Discover the most popular places to visit in Winona

A river winding through a valley with a highway running alongside it.
Photo by Amy Jo Marks
Open Photo by Amy Jo Marks

Sugar Loaf Bluff

9.0/10 (193 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.
See properties

Winona Hotel Deals

A hotel room with a large bed, a separate bathroom with a bathtub, a desk with a chair, and a large mirror.

AmericInn by Wyndham Winona

AmericInn by Wyndham Winona
3.0 star property
1.6 km from Winona
9.0 out of 10, Wonderful, (1,002 reviews)
"This hotel was in the perfect area if you’re planning on visiting a loved one in Winona. We made a weekend trip down here to visit our cousin that’s a WSU student and we had so much fun! The continental breakfast was delicious, the hot tub and pool were clean and fun. And the staff were so friendly!"
The price is CA $190
CA $212 total
includes taxes & fees
Dec 4 - Dec 5
AmericInn by Wyndham 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.
See all properties in Winona

Frequently Asked Questions

How much does a Winona vacation package cost?

You can pick up a vacation package to this top destination from CA $758 on Expedia. However, how much your vacation to Winona costs will depend on factors like the length of stay, season and hotel choice.

What are the cheapest months to go to Winona?

You can generally find lower prices and better availability in December, January and February. Explore our cheap Winona vacation packages and you could score some excellent off-season deals.

How many days is enough for Winona?

With a well-organized schedule, you can easily visit the top Winona attractions in a handful of days. But if you prefer to discover hidden spots or take day trips, consider booking your Winona vacation for longer.

Is it worth booking a vacation package to Winona?

Winona offers everything you need for a wonderful trip. Begin your Winona vacation on a high note by exploring major attractions like Lake Park.

How to find the best Winona package deals?

Use Expedia's handy filters to help you find some tempting Winona package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Winona package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.

Is it cheaper to book a Winona vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights separately. Better still, you can customize your Winona getaway to fit your exact style. Choose 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?

Secure incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Winona break.

How to plan a trip to Winona?

  1. Choose your dates: The things you want to do in Winona and your preferred season can help you decide when to get away.
  2. Set a budget: Factor in expenses such as transportation, flights and meals when calculating how much to put aside for your trip to Winona. Then, select a property that works with your budget, whether that's an affordable stay or a lavish getaway.
  3. Decide your trip length: Think about how long you'd like to spend discovering Winona. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the perfect Winona vacation package for you.

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