Winona Vacations from $264

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The Latest Winona vacation packages

Price found within the past 48 hours. Click for updated prices.
Bertram Inn at Glenmoor

Bertram Inn at Glenmoor

3.5 out of 5
Save 100% on your flight
Price was $384, price is now $264 per person
$264
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Akron (CAK)
8.6/10 Excellent! (296 reviews)
Staff kind and helpful. None of the restaurants open. Hot tub out of order. Would love to stay there again in the summer.

Reviewed on Jan 29, 2026

Comfort Suites Hartville - North Canton

Comfort Suites Hartville - North Canton

2.5 out of 5
Save 100% on your flight
Price was $396, price is now $292 per person
$292
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Akron (CAK)
9.6/10 Exceptional! (1,001 reviews)
I love staying at this hotel. All of the employees are friendly and good at their jobs, the room is spacious, comfortable and clean, the breakfast is nicely stocked and taken care of and the location is good for my needs. I will return again and again.

Reviewed on Feb 26, 2026

Cambria Hotel Akron - Canton Airport

Cambria Hotel Akron - Canton Airport

3 out of 5
Save 100% on your flight
Price was $370, price is now $287 per person
$287
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Akron (CAK)
9/10 Wonderful! (976 reviews)
Room was a bit dirty, didn’t have a remote for the other television, also didn’t have any blankets for the sofa bed. There was a lot of crumbs on the floor like it wasn’t vacuumed . Also it was very noisy because there were several children running around all night in the halls and knocking on doors and running . I was in room 219

Reviewed on Feb 1, 2026

Courtyard by Marriott Canton

Courtyard by Marriott Canton

3 out of 5
Save 100% on your flight
Price was $380, price is now $297 per person
$297
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Akron (CAK)
8.4/10 Very Good! (951 reviews)
Everything about my stay was wonderful! Lynn, at the front desk, is amazing! I stay here every time I visit Canton!! Highly recommend!!

Reviewed on Feb 15, 2026

Courtyard by Marriott Akron Stow

Courtyard by Marriott Akron Stow

3 out of 5
Save 100% on your flight
Price was $402, price is now $319 per person
$319
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Akron (CAK)
8.8/10 Excellent! (871 reviews)
Staff was very responsive to our needs and requests.

Reviewed on Feb 27, 2026

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Winona Hotel Deals

Quality Inn & Suites North Lima - Boardman

Quality Inn & Suites North Lima - Boardman

2.5 out of 5
9988 Market St North Lima OH
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $87 total per night from Mar 9 to Mar 10
$87 total
Mar 9 - Mar 10
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
There was somebody stomping above us at 2am. Very noisy hotel u can hear through the walls. I payed for two queen beds and those were not queens. Very dirty place and weird smells throughout the building

Reviewed on Mar 1, 2026

Quality Inn & Suites North Lima - Boardman
Hampton Inn & Suites Youngstown-Canfield

Hampton Inn & Suites Youngstown-Canfield

2.5 out of 5
6690 Ironwood Blvd Canfield OH
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $122 total per night from Mar 10 to Mar 11
$122 total
Mar 10 - Mar 11
Total with taxes and fees
9.2/10 Wonderful! (696 reviews)
No hot water for shower slow drain. Front desk staff very nice. I did not let staff know about hot water drain issue.

Reviewed on Feb 26, 2026

Hampton Inn & Suites Youngstown-Canfield
Comfort Inn Alliance

Comfort Inn Alliance

2.5 out of 5
2222 Quality Dr. Alliance OH
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $86 total per night from Mar 22 to Mar 23
$86 total
Mar 22 - Mar 23
Total with taxes and fees
8/10 Very Good! (742 reviews)
debris in rear

Reviewed on Mar 2, 2026

Comfort Inn Alliance
See all 117 properties in 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.

Find the Best Winona Vacation Packages

Winona Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Winona vacation package cost?
You'll find cheap prices from $264 on Expedia for your Winona break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Winona costs.
What are the cheapest months to go to Winona?
You can generally find lower prices and greater availability in January, July and October. Explore our cheap Winona vacation packages and you could land some excellent off-season deals.
How many days is enough for Winona?
The ideal duration for your Winona vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to tick off all the leading sights and discover some hidden treasures along the way.
How to find the best Winona package deals?
Landing a cheap Winona package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most affordable Winona package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Winona vacation as a package?
You can enjoy significant savings on your next Winona retreat by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winona?
If you've got your Winona travel dates locked in, book as early as you can to score some terrific deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for setting off on a whim.
Does Expedia offer Book Now, Pay Later Winona vacation packages?
Set off on your dream trip to Winona with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snag great deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.