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 ฿3,374 per night from 1 Feb to 2 Feb
฿3,374
฿3,767 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! (365 reviews)
The owner/innkeeper was lovely! A very nice host and the property is absolutely gorgeous! Truly a dream! Each room is decorated beautifully in time-accurate furnishings and feels very homey. The breakfast was delicious as well, curated and cooked by the host himself. A wonderful evening/stay for ...

Reviewed on 21 Dec 2025

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 ฿5,126 per night from 16 Feb to 17 Feb
฿5,126
฿5,722 total
16 Feb - 17 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 ฿3,161 per night from 8 Feb to 9 Feb
฿3,161
฿3,529 total
8 Feb - 9 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
The price is ฿1,938 per night from 26 Jan to 27 Jan
฿1,938
฿2,202 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 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
The Plaza Hotel & Suites Winona

The Plaza Hotel & Suites Winona

3 out of 5
1025 Highway 61 E Winona MN
The price is ฿3,907 per night from 21 Jan to 22 Jan
฿3,907
฿4,361 total
21 Jan - 22 Jan
includes taxes & fees
Stay at this hotel in Winona. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the pool and the helpful staff in their reviews. Popular attractions ...
8.6/10 Excellent! (1,000 reviews)
This motel is very well maintained, very clean. Staff was always very friendly and polite. Warm and comfortable rooms

Reviewed on 5 Jan 2026

The Plaza Hotel & Suites Winona
Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr Winona MN
The price is ฿3,375 per night from 21 Jan to 22 Jan
฿3,375
฿3,767 total
21 Jan - 22 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! (1,001 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