Historic Downtown Winona, MN

Winona

Stopped here on a rainy camping day after watching a movie at the local movie theater- now my kids want to move here! Great and classy coffee shop- beer and wine, food menu and bakery items- also has used books for sale, free WiFi, comfy chairs and long marble bars for socializing. Great spot!

Popular places to visit

Not everywhere in the Midwest is flat. On the boarder of Minnesota and Wisconsin, the town of Winona's beauty will surprise any MidWesterner once they see the rolling hills and beautiful foliage. Fall is a great time to visit to see the leaves changing through the winding roads of Interstate 90. There's even plenty of places to rent kayaks and canoes if you'd like to get on the water! With plenty of local coffee shops and breweries, it's easy to find a place to relax near the Mississippi River. #LifeAtExpedia

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.

Levee Park
Lake Winona Autumn

Lake Park

4.5/5(21 reviews)

Lake Park is just one of the places to see in Winona, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the area's museums.

Lake Park
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
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 Bluff

4/5(62 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.

Sugar Loaf Bluff

Winona County Historical Society

4.5/5(6 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 County Historical Society

Winona County Courthouse

4.5/5(7 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.

Winona County Courthouse

Historic Downtown Winona Hotel Deals

Alexander Mansion Bed and Breakfast

Alexander Mansion Bed and Breakfast

3.5 out of 5
274 East Broadway Winona MN
The price is NT$3,638 per night from Mar 25 to Mar 26
NT$3,638
NT$4,061 total
Mar 25 - Mar 26
includes taxes & fees
Stay at this B&B in Winona. Enjoy free parking, a business center, and daily housekeeping. Popular attractions Winona Arts Center and Watkins Heritage Museum ...
9.8/10 Exceptional! (494 reviews)
Had such a lovely stay and Richard is an amazing host. I had to cut my stay short due to train cancellations and get back to Chicago. Will be coming back. Sorry I didn’t say farewell and the breakfast was perfect

Reviewed on 2026/3/15

Alexander Mansion Bed and Breakfast
Carriage House B&B

Carriage House B&B

3 out of 5
420 Main St Winona MN
The price is NT$4,708 per night from Mar 29 to Mar 30
NT$4,708
NT$5,255 total
Mar 29 - Mar 30
includes taxes & fees
Stay at this B&B in Winona. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Winona Public Library and Altra Federal Credit Union Stadium ...
9.6/10 Exceptional! (89 reviews)
We enjoyed our stay. The house was adorable there were nice touches such as a bottle of wine. We will be back!

Reviewed on 2025/11/3

Carriage House B&B
Super 8 by Wyndham Winona MN

Super 8 by Wyndham Winona MN

2 out of 5
1025 Sugar Loaf Rd Winona MN
The price is NT$1,883 per night from Mar 29 to Mar 30
NT$1,883
NT$2,140 total
Mar 29 - Mar 30
includes taxes & fees
Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (1,002 reviews)
Was good stay. Could kinda tell that they had new carpet in rooms. Person above us was noisy but all was good.

Reviewed on 2026/3/22

Super 8 by Wyndham Winona MN
Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr Winona MN
The price is NT$2,872 per night from Mar 26 to Mar 27
NT$2,872
NT$3,206 total
Mar 26 - Mar 27
includes taxes & fees
Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (1,006 reviews)
Breakfast was nothing to brag about bacon was under cooked and so thin u could see through it. Spts on the ceiling in the bathroom not sure If stain or mold .

Reviewed on 2026/3/24

Express Suites Riverport Inn & Suites
Holiday Inn Express & Suites Winona by IHG

Holiday Inn Express & Suites Winona by IHG

2.5 out of 5
1128 Homer Rd Winona MN
The price is NT$3,447 per night from Apr 5 to Apr 6
NT$3,447
NT$3,848 total
Apr 5 - Apr 6
includes taxes & fees
Book a stay at this family-friendly hotel in Winona. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in ...
9.2/10 Wonderful! (912 reviews)
Only place we stay when visiting Winona, property is starting to show its age

Reviewed on 2026/3/2

Holiday Inn Express & Suites Winona by IHG
The Plaza Hotel & Suites Winona

The Plaza Hotel & Suites Winona

3 out of 5
1025 Highway 61 E Winona MN
The price is NT$3,990 per night from Mar 26 to Mar 27
NT$3,990
NT$4,454 total
Mar 26 - Mar 27
includes taxes & fees
Stay at this hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ...
8.8/10 Excellent! (1,003 reviews)
Great location for everything you want to do in Winona from hiking to eagles to museums. Great visit.

Reviewed on 2026/3/11

The Plaza Hotel & Suites Winona
See all 118 properties in Historic Downtown 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.

Historic Downtown Winona, MN