Historic Downtown Winona Vacations from $452

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Your Historic Downtown Winona Vacation

Take all the stress out of planning your next break with a Historic Downtown Winona vacation package. Soak in the sounds and sights of this appealing neighborhood and experience everything it has to offer. Kick start your trip to Historic Downtown Winona by heading to nearby attractions such as Winona State University, St. Marys University of Minnesota and Sugar Loaf. Whatever your travel goals or budget, booking your dream Historic Downtown Winona vacation is quick and easy with Expedia.

The Latest Historic Downtown Winona Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Aspen Select

Aspen Select

3.5 out of 5
Price was $503, price is now $452 per person
$452
per person
Oct 31 - Nov 2
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rochester (RST)
8.4/10 Very Good! (1,001 reviews)
Everything was great

Reviewed on Aug 23, 2025

Northwood Inn Prairie Du Chien

Northwood Inn Prairie Du Chien

2 out of 5
Southside
Price was $561, price is now $468 per person
$468
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to La Crosse (LSE)
8.4/10 Very Good! (53 reviews)
I expected more from an 8.2 rating.

Reviewed on Aug 23, 2025

Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys

Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys

3 out of 5
Kutzky Park
Price was $511, price is now $468 per person
$468
per person
Oct 31 - Nov 2
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rochester (RST)
9.2/10 Wonderful! (444 reviews)
We had a trailer and the night staff was extremely helpful in providing us on-site parking.

Reviewed on Aug 24, 2025

Comfort Inn & Suites West - Medical Center

Comfort Inn & Suites West - Medical Center

3 out of 5
Price was $498, price is now $462 per person
$462
per person
Oct 31 - Nov 2
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rochester (RST)
9/10 Wonderful! (480 reviews)
The front desk gal during check-in was excellent. She was friendly, courteous, and efficient. I stay here for my annual appointment at Mayo for many reasons, but really appreciate a friendly smile when I arrive.

Reviewed on Aug 25, 2025

Cobblestone Hotel & Suites - Austin

Cobblestone Hotel & Suites - Austin

2.5 out of 5
Price was $525, price is now $489 per person
$489
per person
Oct 31 - Nov 2
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Rochester (RST)
9/10 Wonderful! (576 reviews)
Pool needs some cleaning and hair removal. Otherwise good experience.

Reviewed on Aug 23, 2025

Historic Downtown Winona Hotel Deals

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr, Winona, MN
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from Aug 28 to Aug 29
$123 total
Aug 28 - Aug 29
Total with taxes and fees
8.4/10 Very Good! (1,010 reviews)
"Safe and quiet"

Reviewed on Aug 25, 2025

Express Suites Riverport Inn & Suites
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
$61 nightly
The price is $68 total per night from Sep 1 to Sep 2
$68 total
Sep 1 - Sep 2
Total with taxes and fees
7.4/10 Good! (1,003 reviews)
"The hotel is getting some updates. Bigger patio area, a place to bbq, updating some of the rooms."

Reviewed on Aug 23, 2025

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
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $179 total per night from Aug 28 to Aug 29
$179 total
Aug 28 - Aug 29
Total with taxes and fees
8.6/10 Excellent! (1,003 reviews)
"Not a bad hotel. Little on the spendy side. Was not a fan that the mini fridge is not turned on so if you bring any beverages or leftover food just be prepared that you have to turn the fridge on and wait for it to cool."

Reviewed on Aug 22, 2025

The Plaza Hotel & Suites Winona
See all 122 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Historic Downtown Winona

Winona State University

Winona State University

Enjoy the collegiate vibe when you visit Winona State University, during your trip to Winona. Stroll along the riverfront or experience the area's museums.

Winona State University
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
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.