Deals on vacations and trips to Winona

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Winona flight + hotel vacation packages

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

Aspen Select

3.5 out of 5
Kutzky Park
Price was $746, price is now $643 per person
$643
per person
Apr 5 - Apr 9
found 1 day 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. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a gym on site, and a 24-hour front desk and a terrace are also provided.
The Towers At Kahler Grand Hotel

The Towers At Kahler Grand Hotel

4 out of 5
Downtown Rochester
Price was $1,564, price is now $1,263 per person
$1,263
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Rochester (RST)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free valet parking. Relax with a drink at the bar/lounge and enjoy the free self-serve breakfast each morning.
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 $807, price is now $681 per person
$681
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Rochester (RST)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. There's a rooftop terrace on site, and a 24-hour front desk and a snack bar/deli are also provided.
Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys

Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys

3 out of 5
Kutzky Park
Price was $838, price is now $713 per person
$713
per person
Apr 5 - Apr 9
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Rochester (RST)
This hotel features an indoor pool and a 24-hour gym. Enjoy the hot tub and free perks like buffet breakfast and WiFi in public areas. Self parking, a 24-hour business center, and a terrace are also offered.
The Berkman

The Berkman

3 out of 5
Folwell
Price was $991, price is now $845 per person
$845
per person
Apr 5 - Apr 9
found 1 day 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.

Top Winona hotels deals

AmericInn by Wyndham Winona

AmericInn by Wyndham Winona

2.5 out of 5
303 Pelzer Street Winona MN
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $115 total per night
$115 total
Feb 15 - Feb 16
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 buffet breakfast and free self parking.
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
$65 nightly
The price is $73 total per night
$73 total
Feb 8 - Feb 9
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 business center. Express check-out and laundry facilities are also provided.
Breakfast included
All inclusive
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
$120 nightly
The price is $134 total per night
$134 total
Feb 8 - Feb 9
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
Holiday Inn Express & Suites Winona by IHG

Holiday Inn Express & Suites Winona by IHG

2.5 out of 5
1128 Homer Rd Winona MN
Free Cancellation
$108 nightly
The price is $121 total per night
$121 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Bring the family and enjoy the children's pool, waterslide, and arcade/game room. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
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
$68 nightly
The price is $76 total per night
$76 total
Feb 9 - Feb 10
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
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
$125 nightly
The price is $140 total per night
$140 total
Feb 8 - Feb 9
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
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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 Winona Autumn

Lake Park

4.5/5(21 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.

Lake Park
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

4/5(62 reviews)

Explore the great outdoors at Sugar Loaf, a lovely green space in Winona. Stroll along the riverfront or experience the area's museums.

Sugar Loaf
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.

Pickwick Mill

Frequently asked questions

How much are vacation packages to Winona?
You can find a fantastic hotel + flight bundle for an affordable $643. 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.

Photos of local treasures

Browse Winona vacation photos for more inspiration

Canoes for rent in the summer on Lake Winona in Winona, Minnesota
Canoes for rent in the summer on Lake Winona in Winona, Minnesota
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!
Not everywhere in the Midwest is flat. On the boarder of Minnesota and Wisconsin, the town of Winona's beauty will surprise any MidWesterner once they see the rolling hills and beautiful foliage. Fall is a great time to visit to see the leaves changing through the winding roads of Interstate 90. There's even plenty of places to rent kayaks and canoes if you'd like to get on the water! With plenty of local coffee shops and breweries, it's easy to find a place to relax near the Mississippi River. #LifeAtExpedia
Winona in the fall

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