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

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

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

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

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 ₩170,307 per night from Mar 23 to Mar 24
₩170,307
₩190,105 total
Mar 23 - Mar 24
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 Mar 15, 2026

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 ₩220,392 per night from Mar 24 to Mar 25
₩220,392
₩246,017 total
Mar 24 - Mar 25
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 Nov 3, 2025

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 ₩88,157 per night from Mar 30 to Mar 31
₩88,157
₩100,168 total
Mar 30 - Mar 31
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! (1,000 reviews)
Room wasn’t clean/ dirty side tables. Check in is odd. 6pm check in and you pick up a phone and then staff come out to help. Turn on heat and it smelled like dust immediately. I didn’t have the nice floors in my room, but the carpet appeared pretty new. The view was 0 starts. My window opened to ...

Reviewed on Mar 7, 2026

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 ₩134,461 per night from Mar 22 to Mar 23
₩134,461
₩150,090 total
Mar 22 - Mar 23
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! (1,003 reviews)
Good location for shopping, medical and food. Great staff every time

Reviewed on Mar 20, 2026

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 ₩169,929 per night from Apr 5 to Apr 6
₩169,929
₩189,683 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 Mar 2, 2026

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 ₩186,773 per night from Mar 22 to Mar 23
₩186,773
₩208,483 total
Mar 22 - Mar 23
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! (1,000 reviews)
Great location for everything you want to do in Winona from hiking to eagles to museums. Great visit.

Reviewed on Mar 11, 2026

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