Winona Vacation Packages 2026 from $394

Winona flight + hotel vacation packages

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

Edge Of The Woods Motel

$394

per person

Dec 25 - Dec 27

found 1 day ago

Roundtrip flight included

Chicago (ORD) to La Crosse (LSE)

A picnic area is available at this motel. Take advantage of the free self parking.

SpringHill Suites by Marriott Rochester-Mayo Clinic/St Marys

Kutzky Park

$850

per person

Dec 13 - Dec 17

found 21 hours ago

Roundtrip non-stop flight included

Chicago (ORD) to Rochester (RST)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free continental breakfast each morning.

The Berkman

Folwell

$1,094

per person

Dec 13 - Dec 17

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Rochester (RST)

This aparthotel features a gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free WiFi. Self parking, a 24-hour business center, and a terrace are also offered.

Microtel Inn & Suites by Wyndham Rochester North Mayo Clinic

$644

per person

Dec 13 - Dec 17

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Rochester (RST)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.

Super 8 by Wyndham Austin MN

$668

per person

Dec 13 - Dec 17

found 21 hours ago

Roundtrip flight included

Chicago (ORD) to Rochester (RST)

This hotel features free WiFi in public areas, free newspapers, and free self parking. Enjoy the free on-the-go breakfast each morning. Staff at the 24-hour front desk can provide around-the-clock assistance.

Top Winona hotels deals

Express Suites Riverport Inn & Suites

900 Bruski Dr Winona MN

Free Cancellation

Reserve now, pay when you stay

$120 nightly

$134 total

Nov 4 - Nov 5

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like full breakfast and free self parking.

Pool

Hot Tub

The Plaza Hotel & Suites Winona

1025 Highway 61 E Winona MN

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$140 total

Dec 1 - Dec 2

Total with taxes and fees

This smoke-free hotel features an attached winery, 2 indoor pools, and a restaurant. Enjoy the gym and free perks like continental breakfast and free self parking. You'll appreciate the hot tub, bar/lounge, and laundry facilities.

Pool

Hot Tub

Super 8 by Wyndham Winona MN

1025 Sugar Loaf Rd Winona MN

Free Cancellation

Reserve now, pay when you stay

$61 nightly

$68 total

Nov 19 - Nov 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center, express check-out, and airport shuttle. The front desk is staffed around-the-clock and laundry facilities are on offer.

Breakfast included

Pet friendly

Fairfield Inn & Suites by Marriott Winona

925 Bruski Drive Winona MN

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$150 total

Nov 8 - Nov 9

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.

Pool

Hot Tub

Days Inn by Wyndham Winona

420 Cottonwood Dr Winona MN

Free Cancellation

Reserve now, pay when you stay

$69 nightly

$77 total

Nov 19 - Nov 20

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and free newspapers.

Breakfast included

Pet friendly

AmericInn by Wyndham Winona

303 Pelzer Street Winona MN

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$151 total

Nov 8 - Nov 9

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like full breakfast and free self parking.

Pool

Hot Tub

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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.

Stay near popular Winona attractions

A river winding through a valley with a highway running alongside it.

Sugar Loaf Bluff

9.0/10 (193 reviews)

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

See properties

Frequently asked questions

How much are vacation packages to Winona?

You can find a fantastic hotel + flight bundle for an affordable $394. 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 95 mi 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 40 mi west of the city center. Your other choices are La Crosse Municipal Airport (LSE) (25 mi away from central Winona) and Chippewa Valley Regional Airport (EAU) (55 mi 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.