Historic Downtown Winona Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Historic Downtown Winona

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites New Lisbon

Comfort Inn & Suites New Lisbon

2.5 out of 5
Price was CA $1,228, price is now CA $1,228 per person
CA $1,228
per person
Aug 10 - Aug 13
found 18 hours ago
Roundtrip flight included
Thunder Bay (YQT) to La Crosse (LSE)
8.4/10 Very good! (927 reviews)
Good stay. Quite. Nice pool & whirlpool. Right next to freeway but no freeway noise.

Reviewed on Jul 2, 2026

Edge Of The Woods Motel

Edge Of The Woods Motel

2 out of 5
Price was CA $1,267, price is now CA $1,254 per person
CA $1,254
per person
Aug 10 - Aug 13
found 18 hours ago
Roundtrip flight included
Thunder Bay (YQT) to La Crosse (LSE)
8.8/10 Excellent! (107 reviews)
Great cheap place to stay. Bed and pillows surprisingly comfortable. Staff very welcoming. Will return!

Reviewed on Jun 22, 2026

Historic Downtown Winona Hotel Deals

Alexander Mansion Bed and Breakfast

Alexander Mansion Bed and Breakfast

3.5 out of 5
274 East Broadway Winona MN
The price is CA $163 per night from Jul 13 to Jul 14
CA $163
CA $181 total
Jul 13 - Jul 14
includes taxes & fees
9.8/10 Exceptional! (523 reviews)
"Beautiful historic property with multi course outstanding breakfast. Very welcoming place. Highly recommended."

Reviewed on Jul 6, 2026

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 CA $176 per night from Jul 12 to Jul 13
CA $176
CA $196 total
Jul 12 - Jul 13
includes taxes & fees
9.6/10 Exceptional! (93 reviews)
"Delicious breakfast, charming property. Much more fun than a sterile hotel. Thank you!"

Reviewed on Jun 8, 2026

Carriage House B&B
The Exchange 14 | Historic Bldg, Studio, Dwntwn

The Exchange 14 | Historic Bldg, Studio, Dwntwn

Winona MN
10/10 Exceptional! (13 reviews)
"Very clean & cute space right in the heart of down town. Highly recommend!!"

Reviewed on May 30, 2026

Get rates
The Exchange 14 | Historic Bldg, Studio, Dwntwn
See all 120 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.
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Frequently asked questions

How much does a Historic Downtown Winona vacation package cost?
We make it simple to see the world, with Historic Downtown Winona vacation packages starting from as low as CA $1,228. You'll have the flexibility to bundle your favorite 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 vacation 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 vacation 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 vacation?
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 vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation 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 vacation 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 vacation 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.

Stay near popular Historic Downtown Winona attractions

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 theater scene.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.