Winona Vacations 2026 from CA $944

Winona flight + hotel packages

Price found within the past 48 hours. Click for updated prices.

Comfort Inn & Suites New Lisbon

CA $944

per person

May 9 - May 11

found 1 day ago

Roundtrip non-stop flight included

Calgary (YYC) to La Crosse (LSE)

Book a stay at this business-friendly hotel in New Lisbon. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions New Lisbon Memorial Library and Burr Oak Winery are located nearby.

Top Winona hotels deals

AmericInn by Wyndham Winona

303 Pelzer Street Winona MN

Free cancellation

Reserve now, pay when you stay

CA $136

CA $152 total

Mar 15 - Mar 16

includes taxes & fees

Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Remlinger Muscle Cars and Westfield Golf Club are located nearby.

Pool

Hot tub

Super 8 by Wyndham Winona MN

1025 Sugar Loaf Rd Winona MN

Free cancellation

Reserve now, pay when you stay

CA $86

CA $98 total

Mar 8 - Mar 9

includes taxes & fees

Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Sugar Loaf Trailhead and Sugar Loaf Bluff are located nearby.

Breakfast included

Pet-friendly

Holiday Inn Express & Suites Winona by IHG

1128 Homer Rd Winona MN

Free cancellation

CA $142

CA $158 total

Apr 5 - Apr 6

includes taxes & fees

Book a stay at this family-friendly hotel in Winona. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Sugar Loaf Trailhead and Sugar Loaf Bluff are located nearby.

Pool

Hot tub

Express Suites Riverport Inn & Suites

900 Bruski Dr Winona MN

Free cancellation

Reserve now, pay when you stay

CA $123

CA $137 total

Mar 8 - Mar 9

includes taxes & fees

Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Sugar Loaf Trailhead and Sugar Loaf Bluff are located nearby.

Pool

Hot tub

Fairfield Inn & Suites by Marriott Winona

925 Bruski Drive Winona MN

Free cancellation

Reserve now, pay when you stay

CA $165

CA $184 total

Apr 5 - Apr 6

includes taxes & fees

Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Sugar Loaf Trailhead and Sugar Loaf Bluff are located nearby.

Pool

Hot tub

Days Inn by Wyndham Winona

420 Cottonwood Dr Winona MN

Free cancellation

Reserve now, pay when you stay

CA $93

CA $104 total

Mar 8 - Mar 9

includes taxes & fees

Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Remlinger Muscle Cars and Fitzgerald Library are located nearby.

Breakfast included

Pet-friendly

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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.

Popular places to visit

Lake Park

Lake Park is just one of the places to see in Winona, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or experience the area's museums.

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.

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 Bluff

Learn about the local history of Winona with a stop at Sugar Loaf Bluff. Stroll along the riverfront or experience the area's museums.

Winona Vacations

A bit of research and planning can mean the difference between a run-of-the-mill vacation and a sensational one! Wander wisely in Winona by knowing some basic facts about it before you hurry off.

The state capital of Minnesota, St. Paul, is located 100 miles (161 kilometers) to the northwest. What's more, you'll find La Crosse 25 miles (40 kilometers) to the southeast.

This area of Southeast Minnesota has a population of about 28,000 people.

Places to visit in Winona

As time goes by, forces of nature sculpt the ground into breathtaking structures like Sugar Loaf. Check out this renowned attraction and discover what makes it so outstanding. Seeking more options? If the kids are tired of sightseeing and need to run around a bit, why not take them to Garvin Heights City Park? It's the ideal spot to have a game of catch and kick a ball around.

Where do you fly into for Winona?

Touching down at Rochester International Airport (RST)? Once you hop off the plane, the middle of Winona is about 45 miles (72 kilometers) east from here. Hail down a taxi and enjoy the drive — your vacation has just begun!

Frequently asked questions

How much are vacation packages to Winona?

You can find a fantastic hotel + flight bundle for an affordable CA $944. With a Travelocity vacation package, an escape to Winona has never looked so good! Save both time and money and get an early start with packing your suitcases.

How long should my Winona vacation be?

Generally, 2 nights is how long the majority of people spend exploring the sights of Winona. Not sure if that'll be enough time to do everything on your to-do list? Stay a few more nights to make the most of your trip.

Where can I get the best vacation package deals for Winona?

Head straight to Travelocity. With access to 400 airlines and a whopping 1,000,000 properties worldwide, selecting the perfect Winona package deal couldn't be simpler.

Why should I purchase my Winona vacation package with Travelocity?

With our Price Match Guarantee, we'll match any cheaper price you find. Add on our 24/7 customer support and top-quality service and the vacation of your dreams is well within reach.

Can I save money on my Winona car rental if I bundle it with hotels and flights?

With a Winona vacation package, you can bundle your flight, hotel and car bookings and save some serious money. If you want to explore the best of this awesome part of the world, why not check out Mall of America? This top attraction is 153 kilometers from Winona. With your own rental car, you'll be there soon enough.

Which airport is best for Winona?

Rochester Intl. Airport (RST) is one of the best airports for Winona. It's around 64 kilometers west of the city center. Your other choices are La Crosse Municipal Airport (LSE) (40 kilometers away from central Winona) and Chippewa Valley Regional Airport (EAU) (88 kilometers away from central Winona).

What is there to do in Winona?

While veering off the tourist trail is rewarding, you really shouldn't miss the popular attractions that make a destination famous. Winona State University and St. Mary's University of Minnesota are a couple of them in Winona.

Where should I stay when visiting Winona?

If you're searching for someplace comfortable to lay your head, check out the Express Suites Riverport Inn & Suites. It's the top pick for many visitors.