Winona Vacation Packages

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Your Winona Vacation

With one of our vacation packages to Winona, you'll discover endless opportunities for fun and relaxation. There's plenty to experience, including its outdoorsy activities and spectacular views. Love to explore your new surroundings? Montgomery County Performing Arts Center, Winona Country Club and Middleton Cemetery are just three of the best places to visit during a trip to Winona. A few clicks is all it takes to create the perfect Winona vacation on Expedia.

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Winona Hotel Deals

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

2.5 out of 5
413 SE Frontage Road, Winona, MS
Fully refundable
The price is CA $158 per night from Aug 8 to Aug 9
CA $158
CA $172 total
Aug 8 - Aug 9
includes taxes & fees
8.2/10 Very Good! (641 reviews)
"Friendly"

Reviewed on Jul. 14, 2025

Holiday Inn Express and Suites Winona North by IHG
Americas Best Value Inn Winona

Americas Best Value Inn Winona

2 out of 5
301 SE Frontage Road, Winona, MS
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Jul 19 to Jul 20
CA $136
CA $148 total
Jul 19 - Jul 20
includes taxes & fees
8/10 Very Good! (415 reviews)
"I like the price but I didn't like that they don't change the sheets the every day and they don't have air freshner in the rooms"

Reviewed on Jun. 27, 2025

Americas Best Value Inn Winona
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82, Winona, MS
The price is CA $87 per night from Jul 19 to Jul 20
CA $87
CA $94 total
Jul 19 - Jul 20
includes taxes & fees
5.6/10 (40 reviews)
"Enjoyed my stay!"

Reviewed on Dec. 9, 2024

Relax Inn & Suites
See all 64 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winona vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Winona costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winona?
December, January and February are great times to look for cheap Winona vacation packages. Choosing to travel in less busy periods means you can usually find lower prices on hotels and flights.
How many days is enough for Winona?
When planning your Winona vacation, a few days will be enough to tour the top spots. Be sure to stop by Winona Country Club — it's one of the leading attractions in this destination. If you're looking for more adventure, think about basing yourself here and going on some tours from Winona.
How to find the best Winona package deals?
Begin your search for a Winona package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect 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 help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still get the freedom 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 have your Winona vacation dates locked in, book as soon as you can to score some awesome deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Winona?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Winona.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to flights and activities. Your hotel will probably be the biggest expense during your trip to Winona.
  3. Work out your trip length: Consider how long you'd like to spend discovering Winona. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a personalized Winona vacation package.

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