Winona Vacation Packages 2025/2026

Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.

Comfort Inn Willow Springs US 60 and US 63

$762

per person

Jan 12 - Jan 16

found 1 day ago

Roundtrip non-stop flight included

Daytona Beach (DAB) to Fort Leonard Wood (TBN)

18.4/10 Exceptional! (541 reviews)

Everything was outstanding. Service was top notch. Everything was clean and the staff extremely excellent.

Reviewed on Nov 13, 2025

Don't see what you're looking for?

See all available trips from Columbus to Winona

View all trips

Discover the most popular places to visit in Winona

Beautiful area. Easy to get up close and not too far off the main road. 🏞 #waterfalls #nature #explore #missouri

Rocky Falls

4.5/5(2 reviews)

Commune with nature and explore the great outdoors at Rocky Falls during your travels in Winona. While you're in the area, wander around the natural setting.

Winona Hotel Deals

“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.

Winona MO

9.8/10 Exceptional! (14 reviews)

Host is very responsive and a joy to work with

Reviewed on Oct 30, 2025

Get rates

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

Eminence MO

9.8/10 Exceptional! (73 reviews)

This was probably the nicest house that we have ever rented. It was exceptionally clean! You could not ask for a better location as you are situated in-between the Current and Jack's Fork rivers.

Reviewed on Oct 13, 2025

Get rates

Echo Bluff State Park

34489 Echo Bluff Dr Eminence MO

Fully refundableReserve now, pay when you stay

$148 nightly

$157 total

Dec 4 - Dec 5

Total with taxes and fees

9.4/10 Exceptional! (214 reviews)

Fireplace was a nice surprise. Love that they had a ceiling fan. Staff was friendly and helpful.

Reviewed on Nov 18, 2025

See all 147 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
Population	1,350
Max Temp Winter	45ºF
Max Temp Summer	90ºF

More vacations you might like

Frequently asked questions

How much does a Winona vacation package cost?

You can pick up a vacation package to this popular destination from $762 on Expedia. However, how much your vacation to Winona costs will depend on your hotel choice, season and length of stay.

What are the cheapest months to go to Winona?

If you're hoping to book a cheap Winona vacation package, consider planning a trip in August, September and October. You'll usually find better prices on flights and accommodations during these months — perfect for travelers wishing to save money.

How many days is enough for Winona?

With a well-organized travel plan, you can easily visit the most popular Winona sights in a few days. But if you'd like to discover hidden spots or take day trips, consider booking your Winona vacation for longer.

How to find the best Winona package deals?

Begin your search for a Winona package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Winona package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Winona adventure off to a flying start.

Is it cheaper to book a Winona vacation as a package?

Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically score a better deal than booking each component individually. And you'll still have the flexibility to create a customized Winona vacation by choosing your preferred airline, accommodation type and car class.

When to book a vacation package to Winona?

If you've got your Winona vacation dates finalized, book early to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for impromptu escapes.

Does Expedia offer Book Now, Pay Later Winona vacation packages?

Set off on your dream trip to Winona with help from our Book Now, Pay Later vacations. No need to save like crazy or wait for payday — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily budget for your trip and snap up bargains before they sell out.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

Winona Vacations from $762

Book a Hotel + Flight or Car together to unlock savings

Room 1

Plan, book, travel with confidence

Better together

Find the right fit

Rest easy