Book Exclusive Winona Vacation Packages

Choose one or more items to build your trip:

Winona flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Gundersen Hotel & Suites

Gundersen Hotel & Suites

2.5 out of 5
Powell-Poage-Hamilton
Price was CA $1,487, price is now CA $1,292 per person
CA $1,292
per person
Sep 28 - Oct 4
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to La Crosse (LSE)
Book a stay at this business-friendly hotel in La Crosse. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions City Brewery and Mary of the Angels Chapel are located nearby.
Aspen Select

Aspen Select

3.5 out of 5
Kutzky Park
Price was CA $1,637, price is now CA $1,335 per person
CA $1,335
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (RST)
Book a stay at this business-friendly hotel in Rochester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Mayo Civic Center and Apache Mall are located nearby.
The Berkman

The Berkman

3 out of 5
Folwell
Price was CA $2,212, price is now CA $1,891 per person
CA $1,891
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (RST)
Book a stay at this golf aparthotel in Rochester. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Kutzky Park Tennis Center and Cascade Lake Beach are located nearby.
Aspen Suites

Aspen Suites

3 out of 5
Price was CA $1,810, price is now CA $1,586 per person
CA $1,586
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (RST)
Book a stay at this business-friendly hotel in Rochester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Kutzky Park Tennis Center and Cascade Lake Beach are located nearby.
Hotel Indigo Rochester – Mayo Clinic Area by IHG

Hotel Indigo Rochester – Mayo Clinic Area by IHG

3.5 out of 5
Downtown Rochester
Price was CA $1,703, price is now CA $1,507 per person
CA $1,507
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (RST)
Book a stay at this business-friendly hotel in Rochester. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Rochester Public Library and Shops University Square are located nearby.

Top Winona hotels deals

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr Winona MN
Free cancellation
Reserve now, pay when you stay
The price is CA $165 per night
CA $165
CA $184 total
Aug 25 - Aug 26
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
Super 8 by Wyndham Winona MN

Super 8 by Wyndham Winona MN

2 out of 5
1025 Sugar Loaf Rd Winona MN
Free cancellation
Reserve now, pay when you stay
The price is CA $85 per night
CA $85
CA $97 total
Sep 14 - Sep 15
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
The Plaza Hotel & Suites Winona

The Plaza Hotel & Suites Winona

3 out of 5
1025 Highway 61 E Winona MN
Free cancellation
Reserve now, pay when you stay
The price is CA $227 per night
CA $227
CA $253 total
Aug 25 - Aug 26
includes taxes & fees
Stay at this hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool 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

Fairfield Inn & Suites by Marriott Winona

3 out of 5
925 Bruski Drive Winona MN
Free cancellation
Reserve now, pay when you stay
The price is CA $185 per night
CA $185
CA $206 total
Aug 30 - Aug 31
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

Days Inn by Wyndham Winona

2 out of 5
420 Cottonwood Dr Winona MN
Free cancellation
Reserve now, pay when you stay
The price is CA $94 per night
CA $94
CA $104 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free parking, and a 24-hour fitness center. 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
AmericInn by Wyndham Winona

AmericInn by Wyndham Winona

3 out of 5
303 Pelzer Street Winona MN
Free cancellation
Reserve now, pay when you stay
The price is CA $163 per night
CA $163
CA $181 total
Sep 20 - Sep 21
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
Don't see what you're looking for?
See all available properties in Winona
View all properties
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 calm lake reflecting yellow and green trees, surrounded by a forested hillside.

Lake Park

9.0/10 (43 reviews)
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.
See properties

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 $1,292. 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.

Photos of local treasures

Browse Winona vacation photos for more inspiration

A stone wall with a hole, overlooking a river and a town.
Two people sitting on a bench facing a sunset over a calm lake.
A frozen river with ice formations and a sunset in the background.
A bridge over a calm river at dusk with lights reflecting on the water.
Swans in icy river