Historic Downtown Winona Vacations from $668
Book a Hotel + Flight or Car together to unlock savings
Your Historic Downtown Winona Vacation
Take all the stress out of planning your next break with a Historic Downtown Winona vacation package. Soak in the sounds and sights of this appealing neighborhood and experience everything it has to offer. Kick start your trip to Historic Downtown Winona by heading to nearby attractions such as Winona State University, St. Marys University of Minnesota and Sugar Loaf. Whatever your travel goals or budget, booking your dream Historic Downtown Winona vacation is quick and easy with Expedia.
The Latest Historic Downtown Winona Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Gundersen Hotel & Suites
Powell-Poage-Hamilton
$668
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip flight included
San Juan (SJU) to La Crosse (LSE)
9.4/10 Exceptional! (1,000 reviews)
The room was clean, the staff was friendly and helpful. We would definitely stay again when in the area!
Reviewed on Sep 22, 2026
Pearl Street Hotel & Suites
Historic Downtown La Crosse
$1,443
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip flight included
San Juan (SJU) to La Crosse (LSE)
8/10 Very Good! (586 reviews)
The room itself was clean, spacious and comfortable. The common areas of the property were worn and in some cases shabby. My guess is that the owners bought the property, put little money into it, and plan to sell the property as a tear-down. Signage from the Holiday Inn era is still up. Use less deodorizing cleaner. The location is valuable as it is across the street from a convention center. Also close to gorgeous riverfront.
Reviewed on Sep 22, 2026
Historic Downtown Winona Hotel Deals
Alexander Mansion Bed and Breakfast
274 East Broadway Winona MN
$106 nightly
$118 total
Oct 22 - Oct 23
Total with taxes and fees
Carriage House B&B
420 Main St Winona MN
$121 nightly
$135 total
Sep 27 - Sep 28
Total with taxes and fees
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
Winona MN
$171 nightly
$190 total
Sep 28 - Sep 29
Total with taxes and fees
10/10 Exceptional! (32 reviews)
"Great home. Clean and comfortable. Great location to all of Winona's top spots. Would recommend."
Reviewed on Sep 16, 2026
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 Historic Downtown Winona attractions
Levee Park
Levee Park is just one of the places to see in Winona, so why not enjoy the other things to explore during your travels? Experience the area's live music and theater scene.
Winona County Historical Society
8.2/10 (37 reviews)
You can spend time browsing the exhibits at Winona County Historical Society during your travels in Winona. Discover the area's festivals and churches.
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.
Winona County Courthouse
8.2/10 (26 reviews)
After visiting Winona County Courthouse, make a plan to see the other sights and activities in Winona. Amble around the area's gardens or experience its festivals.
Merchants Bank
7.8/10 (44 reviews)
You can find out about the history of Winona with a visit to Merchants Bank. Amble around the area's gardens or experience its festivals.
Polish Cultural Institute & Museum Annex
10.0/10 (1 review)
You can spend time exploring the galleries in Polish Cultural Institute & Museum Annex during your trip to Winona. Discover the area's festivals and churches.
Winona City Hall
After visiting Winona City Hall, make a plan to see the other sights and activities in Winona. Discover the area's live music and spas.
Winona Arts Center
Enjoy an outing to Winona Arts Center during your stay in Winona. Discover the area's live music and spas.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.