Winona Vacations

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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.

Discover the most popular places to visit in Winona

Winona Country Club

Enjoy a round of golf in Winona at Winona Country Club.

Winona Country Club

Middleton Cemetery

Enjoy a stop at Middleton Cemetery, a landmark worth seeing in Winona. Take in the theater scene while you're in the area.

Middleton Cemetery

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
$111 nightly
The price is $121 total per night from Sep 8 to Sep 9
$121 total
Sep 8 - Sep 9
Total includes taxes and fees
8.2/10 Very Good! (648 reviews)
"Great hotel"

Reviewed on Aug 8, 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
$99 nightly
The price is $108 total per night from Aug 12 to Aug 13
$108 total
Aug 12 - Aug 13
Total includes taxes and fees
8/10 Very Good! (420 reviews)
"Nothing fancy but a great location and nice breakfast options."

Reviewed on Aug 6, 2025

Americas Best Value Inn Winona
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82, Winona, MS
$70 nightly
The price is $76 total per night from Aug 12 to Aug 13
$76 total
Aug 12 - Aug 13
Total includes taxes and fees
5.6/10 (41 reviews)
"Met all of our needs: clean, quiet, frig, microwave, AC. Bed had unexpectedly luxurious and soft sheets."

Reviewed on Jul 23, 2025

Relax Inn & Suites
See all 67 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 grab a vacation package to this top destination on Expedia. However, how much your vacation to Winona costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Winona?
You can generally find reduced prices and better availability in November, December and January. Take a look at our cheap Winona vacation packages and you could get some great off-season discounts.
How many days is enough for Winona?
You can easily explore all the top sights in Winona in a few days, including the must-see Middleton Cemetery. If you're looking for an extended Winona vacation, check out what sort of activities and day trips are available close by.
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 select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Winona package deal right away, simply tweak your dates and search again. Bear 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?
An Expedia vacation package could land you significant savings when compared to booking flights and accommodations separately. Better still, you can personalize your Winona trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Winona?
If you have your Winona vacation dates finalized, book as early as you can to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for quick escapes.
Does Expedia offer Book Now, Pay Later Winona vacation packages?
Jet off on your dream escape to Winona with our Book Now, Pay Later vacations. No need to scrimp and save or hold off until your next paycheck — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stay on budget and snap up cheap 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.