Historic Downtown Winona Vacations

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Price found within the past 48 hours. Click for updated prices.
  • Room, 2 Queen Beds, Non Smoking (Pet-Friendly) | Individually decorated, individually furnished, desk, laptop workspace
    Jul 13 - Jul 20

    Super 8 by Wyndham Winona MN + Flight

    Winona
    7 nights
    2.0 star property
    7.8/10 - Good (1,002 reviews)
    "No cart to move bags from vehicle to my room. Only a half roll of toilet paper in bathroom with no extras"
    Reviewed May 26, 2026
    Roundtrip • Tokyo (HND) - Rochester (RST)
    HND - RST • 1 stop RST - HND • 1 stop
    ￥260,033
    ￥256,523
    per traveler
    found 1 day ago
    Super 8 by Wyndham Winona MN
  • Exterior
    Jul 13 - Jul 20

    The Wen Inn formerly Andor Wenneson + Flight

    Peterson
    7 nights
    3.0 star property
    9.8/10 - Exceptional (68 reviews)
    "We had a great visit here. Delicious breakfast in the morning. Recommend staying here next time you bike the Root River Trail."
    Reviewed May 22, 2026
    Roundtrip • Tokyo (HND) - Rochester (RST)
    HND - RST • 1 stop RST - HND • 1 stop
    ￥299,050
    ￥282,944
    per traveler
    found 1 day ago
    The Wen Inn formerly Andor Wenneson
  • In-room safe, desk, blackout drapes, iron/ironing board
    Jul 13 - Jul 20

    Days Inn by Wyndham Winona + Flight

    Winona
    7 nights
    2.0 star property
    7.8/10 - Good (1,001 reviews)
    "There were cockroaches in our room! The staff didn't seem surprised and the manager advised me he would comp me $50 for my room but only credited me for $30. We saw them early in the morning around 6am on our last day and had to pack our stuff and leave immediately without showering or sleeping in before checkout. I won't stay at another one of these hotels again nor book through Expedia.com as when we tried to cancel one of the rooms originally, expedia wanted to charge us the same amount for..."
    Reviewed May 27, 2026
    Roundtrip • Tokyo (HND) - Rochester (RST)
    HND - RST • 1 stop RST - HND • 1 stop
    ￥289,580
    ￥276,199
    per traveler
    found 1 day ago
    Days Inn by Wyndham Winona
  • Exterior
    Jul 13 - Jul 20

    Little Bluff Inn + Flight

    Downtown Trempealeau
    7 nights
    2.5 star property
    10/10 - Exceptional (125 reviews)
    "It is not your modern 4 story block hotel. It is a old style hotel, that has been remodeled and looks great. Very clean and modern. It is family friendly, with area’s for the kids to play outside. Big green grassy area’s. A playground. Free bikes to ride. A picnic area and picnic benches for the family to have a get together. The grounds around the property were neat, clean, and flawless. The Wi-Fi was great. It was very pet friendly. I would stay their again, if in the area."
    Reviewed May 24, 2026
    Roundtrip • Tokyo (HND) - Rochester (RST)
    HND - RST • 1 stop RST - HND • 1 stop
    ￥289,141
    ￥282,734
    per traveler
    found 1 day ago
    Little Bluff Inn

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
Fully refundableReserve now, pay when you stay
The price is ￥18,233 per night from Jun 7 to Jun 8
￥18,233
￥20,353 total
Jun 7 - Jun 8
includes taxes & fees
9.8/10 Exceptional! (509 reviews)
"Incredible!! The hosts were the most gracious we have met and clearly love Winona and their home. The food: fantastic. A wine reception, sherry for a nightcap, Irish cream and chocolate for bedtime, and a brilliant home-prepared 4-course breakfast event. No detail was spared in our room or common ..."

Reviewed on May 28, 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 ￥19,734 per night from Jun 22 to Jun 23
￥19,734
￥22,029 total
Jun 22 - Jun 23
includes taxes & fees
9.8/10 Exceptional! (91 reviews)
"Excellent ambience and very helpful staff Have the sumptuous breakfast a bit earlier."

Reviewed on May 5, 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.

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 . 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.

Discover the most popular places to visit in Historic Downtown Winona

St. Mary's University of Minnesota

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

St. Mary's University of Minnesota
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.