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
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

Explore the great outdoors at Sugar Loaf, a lovely green space in Winona. Stroll along the riverfront or experience the area's museums.

Sugar Loaf
Canoes for rent in the summer on Lake Winona in Winona, Minnesota

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 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 ฿3,291 per night from 1 Feb to 2 Feb
฿3,291
฿3,673 total
1 Feb - 2 Feb
includes taxes & fees
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! (366 reviews)
Room was great, the breakfast was the best ever. B&B here should stand for Best/Breakfast. Richard puts on a awesome breakfast. Going to definitely go back!

Reviewed on 18 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 ฿5,135 per night from 14 Feb to 15 Feb
฿5,135
฿5,732 total
14 Feb - 15 Feb
includes taxes & fees
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 ฿3,034 per night from 1 Feb to 2 Feb
฿3,034
฿3,386 total
1 Feb - 2 Feb
includes taxes & fees
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! (901 reviews)
The hotel staff was welcoming. The room was clean and spacious. We enjoyed the free continental breakfast options.

Reviewed on 9 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
Fully refundableReserve now, pay when you stay
The price is ฿1,927 per night from 4 Feb to 5 Feb
฿1,927
฿2,189 total
4 Feb - 5 Feb
includes taxes & fees
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! (1,001 reviews)
Room was very clean. Parking was convenient. The wall heater was noisy and on and off my whole stay which was annoying. There was no local TV channels for winter weather. And you can’t shut off the bathroom fan when the light is on.

Reviewed on 8 Jan 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 ฿3,356 per night from 26 Jan to 27 Jan
฿3,356
฿3,746 total
26 Jan - 27 Jan
includes taxes & fees
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
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 ฿3,538 per night from 22 Feb to 23 Feb
฿3,538
฿3,949 total
22 Feb - 23 Feb
includes taxes & fees
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
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