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 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

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

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 2.786.062 ₫ per night from 19 Feb to 20 Feb
2.786.062 ₫
per night
19 Feb - 20 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 ...
9.8/10 Exceptional! (492 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 3.830.575 ₫ per night from 8 Mar to 9 Mar
3.830.575 ₫
per night
8 Mar - 9 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 2.828.133 ₫ per night from 22 Feb to 23 Feb
2.828.133 ₫
per night
22 Feb - 23 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! (910 reviews)
Breakfast was amazing!

Reviewed on 16 Feb 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 1.324.470 ₫ per night from 18 Mar to 19 Mar
1.324.470 ₫
per night
18 Mar - 19 Mar
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)
The Super 8 is not handicapped accessible. You must navigate stairs to stay on any of the 3 floors.

Reviewed on 17 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 2.368.464 ₫ per night from 1 Mar to 2 Mar
2.368.464 ₫
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. ...
9.2/10 Wonderful! (905 reviews)
Nice clean rooms, friendly staff, excellent continental breakfast, pool and hot were clean and well maintained and workout room was well maintained.

Reviewed on 11 Feb 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 2.804.500 ₫ per night from 19 Feb to 20 Feb
2.804.500 ₫
per night
19 Feb - 20 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 ...
8.6/10 Excellent! (1,000 reviews)
They need to keep the weddings in line more. Didn’t expect a February wedding, but also didn’t expect people to be sprinting and shouting down the halls past midnight, at one point there was a large group yelling in the lobby, blocking the elevator. When I take an elevator at a hotel I paid to stay ...

Reviewed on 10 Feb 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

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