Winona Vacations from $319

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The Latest Winona vacation packages

Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Akron Stow

Courtyard by Marriott Akron Stow

3 out of 5
Save 100% on your flight
Price was $394, price is now $319 per person
$319
per person
Jun 9 - Jun 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Akron (CAK)
8.8/10 Excellent! (940 reviews)
I appreciated the whole staff. Everyone was kind and helpful. The room was in great condition and it was comfortable start to finish. The food (it is pay as you go) however it was delicious and affordable. Will be staying here again.

Reviewed on Apr 27, 2026

Embassy Suites by Hilton Akron Canton Airport

Embassy Suites by Hilton Akron Canton Airport

3.5 out of 5
Price was $978, price is now $798 per person
$798
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Akron (CAK)
9.4/10 Exceptional! (1,001 reviews)
Great breakfast, clean room, wonderful staff - what more can I say?!

Reviewed on Apr 28, 2026

Bertram Inn at Glenmoor

Bertram Inn at Glenmoor

3.5 out of 5
Price was $753, price is now $619 per person
$619
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Akron (CAK)
8.6/10 Excellent! (306 reviews)
Staff were great and it was a fun experience. I would bring my own pillow next time.

Reviewed on Apr 26, 2026

Holiday Inn Express Akron NW - Fairlawn by IHG

Holiday Inn Express Akron NW - Fairlawn by IHG

2.5 out of 5
Price was $828, price is now $689 per person
$689
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Akron (CAK)
8.8/10 Excellent! (826 reviews)
I wish they would have changed the sheets during our 5 night stay. The staff is nice and helpful.

Reviewed on Apr 29, 2026

DoubleTree by Hilton Akron Fairlawn

DoubleTree by Hilton Akron Fairlawn

3 out of 5
Price was $822, price is now $686 per person
$686
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Akron (CAK)
8.6/10 Excellent! (803 reviews)
Perfect choice for our weekend visit. Great location.

Reviewed on May 5, 2026

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Winona Hotel Deals

Courtyard by Marriott Youngstown Canfield

Courtyard by Marriott Youngstown Canfield

3 out of 5
4173 Westford Place Canfield OH
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from May 17 to May 18
$127 total
May 17 - May 18
Total with taxes and fees
9.6/10 Exceptional! (516 reviews)
Excellent in every way!

Reviewed on May 2, 2026

Courtyard by Marriott Youngstown Canfield
Quality Inn & Suites North Lima - Boardman

Quality Inn & Suites North Lima - Boardman

2.5 out of 5
9988 Market St North Lima OH
Fully refundable
$84 nightly
The price is $97 total per night from May 31 to Jun 1
$97 total
May 31 - Jun 1
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
Breakfast was good,room was clean,shower could’ve been a little warmer but it wasn’t bad.no complains at all. I will book their again

Reviewed on May 4, 2026

Quality Inn & Suites North Lima - Boardman
Holiday Inn Express & Suites Alliance by IHG

Holiday Inn Express & Suites Alliance by IHG

2.5 out of 5
2341 W State St Alliance OH
Fully refundable
$101 nightly
The price is $117 total per night from May 17 to May 18
$117 total
May 17 - May 18
Total with taxes and fees
8.2/10 Very Good! (599 reviews)
Feel safe and nice swimming pool!

Reviewed on May 6, 2026

Holiday Inn Express & Suites Alliance by IHG
See all 121 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 $319 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.