Winona Vacations

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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

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.

Rocky Falls

Winona Hotel Deals

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

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

Winona
9.8/10 Exceptional! (8 reviews)
"This is such a cute VRBO! It has all the ammenities you need for a weekend away, and they're all nicer than most VRBOs. The kitchen is perfect. We has no issues checking in, and the owner was very friendly. Just beware that the road is quite rustic and the drive is quite steep. A truck would be ..."

Reviewed on Aug 10, 2025

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“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

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

Eminence
9.8/10 Exceptional! (66 reviews)
Wonderful getaway spot
"Very nice home with all the amenities you'd need for a short or longer stay. Comfortable beds, plenty of space for activities, loved the barn area with games, and secluded enough to have privacy. We really enjoyed our time there and wish we could have stayed longer. The hosts were very kind and available ..."

Reviewed on Jul 17, 2025

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Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
Honeysuckle Inn - Mountain View

Honeysuckle Inn - Mountain View

3 out of 5
1207 E Hwy 60, Mountain View, MO
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $133 total per night from Aug 12 to Aug 13
$133 total
Aug 12 - Aug 13
Total includes taxes and fees
8.4/10 Very Good! (303 reviews)
"Very nice cozy stay"

Reviewed on Jul 21, 2025

Honeysuckle Inn - Mountain View
See all 143 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.

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Frequently asked questions

How much does a Winona vacation package cost?
You can pick up a vacation package to this popular destination 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.