Historic Downtown Winona Vacations from $385

Book a Hotel + Flight or Car together to unlock savings

Photo by Jessica Purdue Rep

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.
Hotel Indigo Rochester – Mayo Clinic Area by IHG

Hotel Indigo Rochester – Mayo Clinic Area by IHG

3.5 out of 5
Downtown Rochester
Price was $604, price is now $385 per person
$385
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Rochester (RST)
8.8/10 Excellent! (867 reviews)
Clean, quiet room and comfortable bed

Reviewed on Dec 7, 2025

Aspen Select

Aspen Select

3.5 out of 5
Price was $640, price is now $450 per person
$450
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Rochester (RST)
8.4/10 Very Good! (1,003 reviews)
Beds are very comfortable!

Reviewed on Dec 10, 2025

Americas Best Value Inn Zumbrota

Americas Best Value Inn Zumbrota

2 out of 5
Save 100% on your flight
Price was $1,567, price is now $1,202 per person
$1,202
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Rochester (RST)
7.2/10 Good! (502 reviews)
Quiet pretty decent

Reviewed on Dec 6, 2025

The Wen Inn formerly Andor Wenneson

The Wen Inn formerly Andor Wenneson

2 out of 5
Price was $538, price is now $414 per person
$414
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rochester (RST)
9.8/10 Exceptional! (56 reviews)
Great property and great host. Right on the Root River Trail for biking.

Reviewed on Oct 27, 2025

Sleep Inn & Suites West-Near Medical Center

Sleep Inn & Suites West-Near Medical Center

2.5 out of 5
Price was $541, price is now $419 per person
$419
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
Nashville (BNA) to Rochester (RST)
9/10 Wonderful! (561 reviews)
Nice stay as usual. No hot food other than waffles on Thanksgiving and the Friday afterwards was disappointing. They have served hot breakfast on Christmas in the past. Front desk person on Friday morning was super nice and helpful. We will be back.

Reviewed on Nov 29, 2025

Historic Downtown Winona Hotel Deals

Carriage House B&B

Carriage House B&B

3 out of 5
420 Main St Winona MN
$148 nightly
The price is $165 total per night from Dec 14 to Dec 15
$165 total
Dec 14 - Dec 15
Total with taxes and fees
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 Nov 3, 2025

Carriage House B&B
Alexander Mansion Bed and Breakfast

Alexander Mansion Bed and Breakfast

3.5 out of 5
274 East Broadway Winona MN
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $146 total per night from Dec 14 to Dec 15
$146 total
Dec 14 - Dec 15
Total with taxes and fees
10/10 Exceptional! (364 reviews)
Yes

Reviewed on Dec 8, 2025

Alexander Mansion Bed and Breakfast
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

Winona MN
$170 nightly
The price is $183 total per night from Dec 15 to Dec 16
$183 total
Dec 15 - Dec 16
Total with taxes and fees
10/10 Exceptional! (20 reviews)
The house was so cozy and comfortable. The decor was great. Beds were very comfortable. The neighborhood was very quiet. You could walk to many establishments. I would highly recommend this VRBO. Our contact was timely and answered our questions efficiently.

Reviewed on Nov 17, 2025

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
See all 121 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

4.5/5(94 reviews)

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

4/5(62 reviews)

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.