Winona Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winona

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 3.005.065 ₫ per night from 13 Jul to 14 Jul
3.005.065 ₫
3.275.520 ₫ total
13 Jul - 14 Jul
includes taxes & fees
8.2/10 Very Good! (630 reviews)
"Staff was helpful I thought hotel needed an update"

Reviewed on 19 Jun 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 2.586.969 ₫ per night from 24 Jun to 25 Jun
2.586.969 ₫
2.819.796 ₫ total
24 Jun - 25 Jun
includes taxes & fees
8/10 Very Good! (407 reviews)
"Good for the price. Little mold in shower, but all pretty clean and safe. Good first come first serve breakfast, but specs of something in waffles."

Reviewed on 16 Jun 2025

Americas Best Value Inn Winona
Relax Inn & Suites
Relax Inn & Suites
2 out of 5
328 US-82, Winona, MS
5.6/10 (40 reviews)
"Enjoyed my stay!"

Reviewed on 9 Dec 2024

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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.

Frequently asked questions

How much does a Winona holiday package cost?
You can grab a holiday package to this top destination on Expedia. However, how much your holiday 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 usually find lower rates and better availability in December, January and February. Check out our cheap Winona holiday packages and you could land some excellent off-season deals.
How many days is enough for Winona?
Typically, a handful of days is ideal for a Winona holiday. With a well-organised schedule, you can check out all the leading attractions like Winona Country Club, as well as discover some hidden gems along the way.
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 holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking flights and accommodation separately. Better still, you can personalise 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 holiday package to Winona?
If you have your Winona holiday 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.
How to plan a trip to Winona?

  1. Choose when to get away: Check your diary and get your bags packed. Your favourite time of year and the activities available will also help you decide when to holiday in Winona.
  2. Calculate your budget: Make sure you have enough money to pay for everything from dining out and transportation to airfares and activities. Your hotel will likely be the biggest expense during your trip to Winona.
  3. Set the duration of your trip: Start by compiling a list of the attractions you want to get to in Winona. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Winona holiday package that brings all your bookings together.

Popular places to visit

Montgomery County Performing Arts Center

You can make plans for a show at Montgomery County Performing Arts Center during your stay in Winona. Take in the theatre scene while you're in the area.

Montgomery County Performing Arts Center

Middleton Cemetery

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

Middleton Cemetery