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Top Winona hotels 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
Free cancellation
The price is CA $165 per night
CA $165
CA $180 total
Jul 12 - Jul 13
includes taxes & fees
Book a stay at this business-friendly hotel in Winona. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Winona - Montgomery County Library and Montgomery County Performing Arts Center are located nearby.
Americas Best Value Inn Winona

Americas Best Value Inn Winona

2 out of 5
301 SE Frontage Road Winona MS
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $151 total
Jun 16 - Jun 17
includes taxes & fees
Book a stay at this business-friendly motel in Winona. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Winona - Montgomery County Library and Montgomery County Performing Arts Center are located nearby.
Relax Inn & Suites

Relax Inn & Suites

2 out of 5
328 US-82 Winona MS
The price is CA $88 per night
CA $88
CA $96 total
Jun 16 - Jun 17
includes taxes & fees
Stay at this motel in Winona. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Winona - Montgomery County Library and Montgomery County Performing Arts Center are located nearby.
Charming 3-bedroom barn in quaint Winona with AC

Charming 3-bedroom barn in quaint Winona with AC

Winona MS
The price is CA $490 per night
CA $490
CA $607 total
Jun 16 - Jun 17
includes taxes & fees
Stay at this vacation home in Winona. Enjoy laundry facilities and air conditioning. Popular attractions Montgomery County Performing Arts Center and Winona - Montgomery County Library are located nearby.
Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Charming 1-bedroom cabin in Winona. Close 50 minutes to Starkville for games.

Winona MS
The price is CA $210 per night
CA $210
CA $261 total
Jun 16 - Jun 17
includes taxes & fees
Stay at this cabin in Winona. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Winona Country Club and Montgomery County Performing Arts Center are located nearby.
Charming ranch style log cabin with AC in scenic Winona

Charming ranch style log cabin with AC in scenic Winona

Winona MS
The price is CA $348 per night
CA $348
CA $431 total
Jun 16 - Jun 17
includes taxes & fees
Stay at this cabin in Winona. Enjoy laundry facilities and air conditioning. Popular attractions Winona Country Club and Montgomery County Performing Arts Center are located nearby.
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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.

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 . 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

Winona County Courthouse