Winona Vacations from $421

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to $1,045 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.

The Latest Winona vacation packages

Price found within the past 48 hours. Click for updated prices.
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
Price was $421, price is now $421 per person
$421
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to University (UOX)
5.8/10 (41 reviews)
Booking through Expedia for this property becomes a hassle when checking in. They never seem to know what's going on.

Reviewed on Dec 9, 2024

Holiday Inn Express and Suites Winona North by IHG

Holiday Inn Express and Suites Winona North by IHG

2.5 out of 5
Price was $555, price is now $526 per person
$526
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to University (UOX)
8.2/10 Very Good! (650 reviews)
Staff were friendly and helpful. Beds were comfortable. Only complaint was shower head, only center holes gave water and pressure was low. We will stay again.

Reviewed on Jul 17, 2025

Americas Best Value Inn Winona

Americas Best Value Inn Winona

2 out of 5
Price was $471, price is now $471 per person
$471
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to University (UOX)
8/10 Very Good! (418 reviews)
Nothing fancy but a great location and nice breakfast options.

Reviewed on Aug 6, 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

Winona Country Club

4.5/5(4 reviews)

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

Winona Country Club

Middleton Cemetery

4/5(6 reviews)

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
$120 nightly
The price is $131 total per night from Sep 7 to Sep 8
$131 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (650 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 23 to Aug 24
$108 total
Aug 23 - Aug 24
Total with taxes and fees
8/10 Very Good! (423 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 23 to Aug 24
$76 total
Aug 23 - Aug 24
Total with 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 66 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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winona vacation package cost?
You can grab a vacation package to this top destination from $421 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.