Historic Downtown Winona Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Jessica Purdue Rep

Top hotels in Historic Downtown Winona

Carriage House B&B

Carriage House B&B

3 out of 5
420 Main St Winona MN
The price is 3.889.723 ₫ per night from 2 Dec to 3 Dec
3.889.723 ₫
4.341.986 ₫ total
2 Dec - 3 Dec
includes taxes & 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 3 Nov 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
10/10 Exceptional! (363 reviews)
Richard was amazing. The house was beautiful and the breakfast will leave you full for hours! If you need more than one bed, take the room with the kitchenette. Its cozy and has a private entrance.

Reviewed on 10 Nov 2025

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Alexander Mansion Bed and Breakfast
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
The price is 2.584.094 ₫ per night from 2 Dec to 3 Dec
2.584.094 ₫
2.884.460 ₫ total
2 Dec - 3 Dec
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
Everything about my stay was great. I interacted with two front desk personnel and the breakfast attendant, all very good at their jobs. The room was nice, and the breakfast bar was very large and good. I was there for a convention, and that space was well done as well. I encouraged the event coordinator ...

Reviewed on 24 Nov 2025

Express Suites Riverport Inn & Suites
See all 123 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.

Frequently asked questions

How much does a Historic Downtown Winona holiday package cost?
We make it simple to see the world, with Historic Downtown Winona holiday packages starting from as low as . You'll have the flexibility to bundle your favourite airlines, hotels and car rental. For the ultimate escape, why not add a couple of experiences and tours to your itinerary?
How do I get a cheap travel package to Historic Downtown Winona?
Bundle your bookings with Expedia to save big bucks on your next exciting adventure. With more than 550 air carriers and 1null000null000 properties globally, your Historic Downtown Winona holiday package can be customized exactly to suit your budget. With all those extra dollars, why not include a few interesting activities and tours? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in Historic Downtown Winona is closer than you thought!
Where should I stay in Historic Downtown Winona?
Stay close to the action. Many people like to book hotels within easy reach of popular attractions, like Winona State University, St. Marys University of Minnesota and Sugar Loaf.
How far in advance should I book my Historic Downtown Winona holiday?
It's tricky picking the best time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available up to a year in advance. If you're unable to do so, don't despair. Discounted prices occasionally appear within a few weeks of departure dates.
What does an Expedia Historic Downtown Winona travel package include?
It comes down to what kind of trip you're contemplating. Historic Downtown Winona travel deals can include hotels, flights and car rentals. You can mix and match to create the travel package that fits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking a Historic Downtown Winona travel package?
Discover deals to match your budget with an Expedia package. Hotels, flights, rental cars — we're a one-stop shop for all of them. You'll save a tidy sum just for bundling your bookings. Whether you're going on a snow and ski adventure or venturing someplace warm, your ideal getaway is only a few clicks away.
Can I choose my airline with a Historic Downtown Winona Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our holiday packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Historic Downtown Winona holiday package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can cancel or change your Historic Downtown Winona holiday package. If you booked in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.

Popular places to visit

Sugar Loaf

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
Pickwick Mill

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

Merchants Bank

You can find out about the history of Winona with a stop at Merchants Bank. Amble around the area's gardens or experience its festivals.

Merchants Bank