Winona Vacations

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Find the Best Winona Vacation Packages

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
9.6/10 Exceptional! (6 reviews)
As advertised!!
"It was a great place!! Close to town. Clean and put together well!! I would tell anyone to go here including ourselves in the future!"

Reviewed on Jul 25, 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
The price is ￥16,278 per night from Aug 4 to Aug 5
￥16,278
￥17,647 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (302 reviews)
"Very nice cozy stay"

Reviewed on Jul 21, 2025

Honeysuckle Inn - Mountain View
See all 142 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.

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?
January, February and November are great times to search for cheap Winona vacation packages. Opting to travel in less busy periods means you'll typically find reduced prices on flights and hotels.
How many days is enough for Winona?
Usually, a handful of days is enough to tick off the major sights during your Winona vacation. But if you want to have time to unwind or take day tours, think about extending your itinerary.
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.
How to plan a trip to Winona?

  1. Choose your dates: The things you'd like to do in Winona and your favorite season can help you decide when to go.
  2. Budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include food, transportation and flights. Also, put aside some extra funds for unexpected costs that could arise during your trip to Winona.
  3. Work out your trip length: Think about how long you'd like to spend exploring Winona. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored Winona vacation package.

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