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.
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Dec 13 - Dec 17
Austin
4 nights
6.6/10 - (470 reviews)
"Love staying here for my mothers-in-law's Mayo appointments. Just 45 minutes away from the hustle & bustle of Rochester so very convenient. Love the dining options in the area as well plus the SPAM Museum! Staff very friendly and drive up room very clean"
Reviewed October 28, 2026
Roundtrip • Chicago (CHI) - Rochester (RST)
ORD - RST • 1 stop RST - ORD • 1 stop
$729
per traveler
found 1 day ago
Dec 13 - Dec 17
Zumbrota
4 nights
7.4/10 - Good (577 reviews)
Roundtrip • Chicago (CHI) - Rochester (RST)
ORD - RST • 1 stop RST - ORD • 1 stop
$748
per traveler
found 1 day ago
Dec 13 - Dec 17
Stewartville
4 nights
8.0/10 - Very good (500 reviews)
Roundtrip • Chicago (CHI) - Rochester (RST)
ORD - RST • 1 stop RST - ORD • 1 stop
$764
per traveler
found 1 day ago
Dec 13 - Dec 17
Rochester
4 nights
7.6/10 - Good (1,063 reviews)
"Nice place!"
Reviewed November 10, 2026
Roundtrip • Chicago (CHI) - Rochester (RST)
ORD - RST • 1 stop RST - ORD • 1 stop
$764
per traveler
found 1 day ago
Dec 13 - Dec 17
Rochester
4 nights
7.6/10 - Good (103 reviews)
Roundtrip • Chicago (CHI) - Rochester (RST)
ORD - RST • 1 stop RST - ORD • 1 stop
$754
per traveler
found 1 day ago
Winona, MN, is a charming town perfect for outdoor enthusiasts and those seeking a relaxing getaway. With its stunning scenery and romantic atmosphere, it offers guest satisfaction for all travelers, including business visitors. Explore the beauty and history that makes Winona a delightful destination.
Photo by Mark Bolcerek
View properties in map for Cochrane
Discover Cochrane, Wisconsin, a charming destination perfect for travelers seeking a family-friendly getaway immersed in nature. Visitors can explore the scenic beauty of John Latsch State Park, delve into local history at the Castlerock Museum, or enjoy the stunning views from the Lock and Dam No. 4 Observation Area. Located about 17 miles by car from Winona, Cochrane offers a delightful escape with a mix of outdoor activities and serene landscapes, making it a smart choice for your next vacation.
Photo by Kayla Schneider
View properties in map for Fountain City
Plan your stay in Fountain City, a top-rated choice for travelers seeking a weekend getaway immersed in nature and family-friendly activities. This charming city offers access to stunning outdoor scenery, including the nearby Merrick State Park and the scenic river and lake, perfect for hiking and exploring. Located about 6 miles by car from Winona, Fountain City makes for an ideal home base to experience local attractions like St. Mary's University and the Minnesota Marine Art Museum, ensuring a memorable vacation.
Photo by Jessica Purdue Rep
View properties in map for Historic Downtown Winona
Make the most of your visit by staying in Historic Downtown Winona, a haven for cultural and outdoor enthusiasts thanks to its rich history and vibrant atmosphere. This charming neighborhood offers easy access to popular attractions like Winona State University, the Minnesota Marine Art Museum, and the scenic Aghaming Park and Preserve. Located around Winona, it provides a perfect base for exploring the area’s unique blend of education, art, and nature. Choosing Historic Downtown Winona for your stay ensures an enriching experience.
View properties in map for Goodview
Immerse yourself in Goodview, where families and adventure seekers can easily access the stunning landscapes of Aghaming Park and Preserve, the artistic treasures at the Minnesota Marine Art Museum, and the vibrant atmosphere of Winona State University. This charming village, nestled in Winona, offers a year-round escape with peak visits from July to September, making it an ideal base for those looking to explore both cultural and outdoor experiences. Booking your stay in Goodview ensures a memorable and enriching getaway.
View properties in map for Stockton
Travelers visiting the area often choose Stockton, especially those with a love for family and nature, seeking a scenic weekend getaway. Nestled within Winona, Stockton offers access to beautiful lakes, rivers, and the Minnesota Marine Art Museum, perfect for a romantic or outdoor experience. The village's moderate seasonal appeal, peaking in July to August and October, ensures visitors can enjoy its recreational areas year-round. With its charming atmosphere, Stockton is a smart choice for your stay in the region.
Photo by Amy Jo Marks
Rating: 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.
Rating: 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."
Photo by Jessica Jahnke
Rating: 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.
Rating: 8.0/10 (32 reviews)
Overlooking Lake Winona, this recreation center 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.
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.
Rating: 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.
Rating: 9.4/10 (13 reviews)
Explore the great outdoors at Garvin Heights City Park, a lovely green space in Winona. Stroll along the riverfront or experience the area's museums.
You can browse for the perfect souvenirs at Winona Mall during your visit to Winona. Stroll along the riverfront or experience the area's museums.
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.
A Winona vacation package typically bundles your round-trip flights, hotel stays, and rental cars. Many hotels in Winona offer free breakfast, providing a convenient start to your day. Some properties also provide airport shuttle services to and from Minneapolis - St. Paul Intl. Airport (MSP), adding ease to your travel plans.
Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.
When you bundle, you can save up to 30%*. To save money on a Winona package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
For couples seeking a romantic Winona vacation package, consider a stay at the 3.5-star Alexander Mansion Bed and Breakfast. Rated 9.8 out of 10, this property costs around $140 per night and offers amenities like free breakfast, a game room, and a kitchen, with travelers frequently praising its beautiful rooms and knowledgeable staff.
Families will find a strong option in a Winona vacation package built around the AmericInn by Wyndham Winona. Rated 8.6 out of 10 and costing around $200 per night, it features family rooms, an indoor pool, and a hot tub, with travelers often highlighting the spacious rooms and amazing staff.
If you're looking for the best value, a Winona vacation package with a stay at Super 8 by Wyndham Winona MN is a great choice. Priced around $100 per night, this hotel includes free breakfast and is pet friendly, with travelers noting its clean rooms and easy check-in experience.
*Package availability and prices may change depending on dates and demand.
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Winona vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
To find last-minute vacation packages to Winona, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
Free cancellation on a Winona vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Winona getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.