Winona Vacations from $424
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Winona vacation packages
Price found within the past 48 hours. Click for updated prices.
Bertram Inn at Glenmoor
$434
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Akron (CAK)
8.6/10 Excellent! (324 reviews)
Beautiful setting, amenities are nice but unless you stay more than one night, not too beneficial. The price of the room was ultimately what drew us there. If you are looking for a normal hotel and modern type rooms, this isn’t for you, but if you want something quiet, spacious, and don’t mind something older, this might be for you. My only real negative is, the AC couldn’t keep up with the temperature outside and it wasn’t even that hot out. Room was constantly at 74 and up while the AC was on around 65.
Reviewed on Sep 21, 2026
Winona Hotel Deals
Quality Inn & Suites North Lima - Boardman
9988 Market St North Lima OH
Fully refundable
$84 nightly
$97 total
Oct 18 - Oct 19
Total with taxes and fees
Postcard Cabins Beaver Creek Ohio, Outdoor Collection by Marriott Bonvoy
45529 Middle Beaver Rd Lisbon OH
$172 nightly
$189 total
Oct 1 - Oct 2
Total with taxes and fees
9.4/10 Exceptional! (50 reviews)
"Lovely place. They had all the amenities needed. The room was clean and check in was easy. It was very quiet and I loved how you got your own fire pit, and picnic table. The snacks/ drinks was an added perk as well. I will definitely be back."
Reviewed on Sep 5, 2026
Comfort Inn Alliance
2222 Quality Dr. Alliance OH
Fully refundable
$93 nightly
$107 total
Oct 19 - Oct 20
Total with taxes and fees
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 |
More vacations you might like
Frequently asked questions
How much does a Winona vacation package cost?
You'll find cheap prices from $424 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.
