Historic Downtown Winona Travel Guide

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!
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 theatre 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
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 when you take a trip to Sugar Loaf Bluff. Stroll along the riverfront or experience the area's museums.

Sugar Loaf Bluff
The old mill is also available for tours

Pickwick Mill

Find out about the history of Winona when you take a trip to Pickwick Mill. Stroll along the riverfront or experience the area's museums.

Pickwick Mill

Winona County Historical Society

You can spend time exploring the galleries in 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

Top hotels in Historic Downtown Winona

Alexander Mansion Bed and Breakfast

Alexander Mansion Bed and Breakfast

3.5 out of 5
274 East Broadway Winona MN
The price is Rp1.810.457 per night from 10 Feb to 11 Feb
Rp1.810.457
per night
10 Feb - 11 Feb
Stay at this B&B in Winona. Enjoy free breakfast, free parking and a business centre. Popular attractions Watkins Heritage Museum and Polish Cultural Institute ...
10/10 Exceptional! (370 reviews)
Room great. Staff great. Guests all had nice conversations at breakfast which was also great. History of house was very interesting.

Reviewed on 31 Jan 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 Rp2.489.210 per night from 4 Mar to 5 Mar
Rp2.489.210
per night
4 Mar - 5 Mar
Stay at this B&B in Winona. Enjoy free breakfast, free Wi-Fi 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 3 Nov 2025

Carriage House B&B
AmericInn by Wyndham Winona

AmericInn by Wyndham Winona

2.5 out of 5
303 Pelzer Street Winona MN
The price is Rp1.735.697 per night from 15 Feb to 16 Feb
Rp1.735.697
per night
15 Feb - 16 Feb
Stay at this business-friendly hotel in Winona. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
9/10 Wonderful! (906 reviews)
Staff was very friendly when we arrived. Our room wasn’t quite ready for us to check in early, she told us to enjoy the pool and she would let us know as soon as it was ready. It was still ready earlier than the check in time.

Reviewed on 26 Jan 2026

AmericInn by Wyndham Winona
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 Rp1.080.064 per night from 12 Feb to 13 Feb
Rp1.080.064
per night
12 Feb - 13 Feb
Stay at this business-friendly hotel in Winona. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in ...
7.6/10 Good! (1,003 reviews)
Clean room, great stay

Reviewed on 3 Feb 2026

Super 8 by Wyndham Winona MN
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 Rp1.822.608 per night from 1 Mar to 2 Mar
Rp1.822.608
per night
1 Mar - 2 Mar
Stay at this family-friendly hotel in Winona. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the helpful staff in their reviews. ...
9/10 Wonderful! (903 reviews)
Breakfast was amazing! Hot tub, pool and sauna were incredible!

Reviewed on 4 Jan 2026

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

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr Winona MN
The price is Rp1.822.439 per night from 10 Feb to 11 Feb
Rp1.822.439
per night
10 Feb - 11 Feb
Stay at this business-friendly hotel in Winona. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
8.4/10 Very Good! (1,000 reviews)
The room was very clean and the staff very friendly and quick to respond! Very pleased with our stay!

Reviewed on 3 Jan 2026

Express Suites Riverport Inn & Suites
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 Travel Guide