Book Exclusive Winona Vacation Packages

Choose one or more items to build your trip:

Winona flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Relax Inn & Suites
Americas Best Value Inn Winona
Holiday Inn Express and Suites Winona North by IHG

Top Winona hotels deals

Don't see what you're looking for?
See all available properties in Winona
View all properties
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.

Popular places to visit

Winona Vacations

Even if you're the most impulsive adventurer, it still doesn't hurt to brush up on one or two things about Winona before you go. Pinpoint it on a map, explore the sights on offer and let the excitement begin!

This town lies 20 miles (32 kilometers) south of Grenada. It's also 25 miles (40 kilometers) east of Greenwood.

The population of this area of Mississippi is around 5,000.

Hotels in Winona

Planning a trip to Winona? Don't leave it too late to reserve one of its 2 available accommodations. After you've made your selection, all that’s left is the fun part — actually being there!

The Holiday Inn Express and Suites Winona North and Americas Best Value Inn & Suites Winona are our favorite accommodations in Winona. Make a reservation and then you'll be able to get down to the good stuff — booking your thrilling travel experiences.

Places to visit in Winona

Not just a retreat for millionaires, country clubs offer sports and recreational activities in a refined setting. If you're feeling swanky, why not take advantage of the facilities available at Winona Country Club? Want more options? You don't need to be a grave hunter or a tombstone tourist to appreciate a walk around Middleton Cemetery. Why not try and find a guided tour and learn some of the history behind this fascinating open-air museum? But there's more. Great theater can challenge our expectations and asks us to aspire to bigger and better things. Get tickets to a show at Montgomery County Performing Arts Center and open your mind to some new ideas.

Where do you fly into for Winona?

There's no better feeling than arriving in an entirely new destination. If you're hopping on a plane to Winona, there's every chance you'll disembark at Leflore Airport (GWO). It's around 20 miles (32 kilometers) to the west of the downtown area. Grab your belongings and get ready for an amazing adventure!

Frequently asked questions

How much are vacation packages to Winona?
You can get a great flight and hotel bundle from just CA $2,357. With a Travelocity vacation package, a getaway to Winona has never looked so good! Save your time and money and get an early start with packing your suitcases.
How long should my Winona vacation be?
Many visitors pack their suitcase and explore the sights of Winona for an average of 2 nights. That’s a great guide, but you’re not bound by it. Whether you only stay a few nights to see the famous attractions or linger a while to uncover off-the-beaten-path gems, an epic adventure awaits.
Where can I get the best vacation package deals for Winona?
It’s simple — head to Travelocity. With no less than 400 partner airlines and 1,000,000 worldwide properties, it’s easy to put together a Winona package deal that ticks all your boxes.
Why should I book my Winona vacation bundle via Travelocity?
We take the stress out of travel planning. Whether you’re looking for an amazing new place to uncover or want to make sure you get the best deal around, we’ve got your back. Our 24/7 support, high-quality service and Price Match Guarantee mean you can book with confidence with Travelocity.
Can I save on my Winona car rental if I bundle it with hotels and flights?
Combining your car, flight and hotel into a Winona vacation package is the easiest way to land the best deal. Plus, having your own car rental gives you absolute freedom to make your way to all those landmarks you’re itching to see. Situated 193 kilometers from Winona, Orpheum Theatre is one attraction that should feature on your itinerary. Put together a driving playlist and make a day trip of it.
What is there to do in Winona?
Montgomery County Performing Arts Center deserves a spot on your to-do list. Once you’ve crossed off this renowned attraction, amble through the streets of Winona and find out what makes this fantastic city tick.
Where should I stay when visiting Winona?
The Holiday Inn Express and Suites Winona North, an IHG Hotel is popular with many visitors. Book soon to avoid missing out.

Photos of local treasures

Browse Winona vacation photos for more inspiration