Historic Downtown Winona Holidays

Photo by Jessica Purdue Rep

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    Save up to S$134 when you book a flight and hotel together*

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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
Fully refundableReserve now, pay when you stay
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

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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 S$212 per night from 28 Dec to 29 Dec
S$212
28 Dec - 29 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
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 S$142 per night from 7 Jan to 8 Jan
S$142
7 Jan - 8 Jan, 2026
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Room was clean and well prepared. Guest service members were very pleasant and nice. Overall, a nice stay.

Reviewed on 2 Dec, 2025

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.

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 1,000,000 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.