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Winona

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Winona Flights as Low as $261

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Cheap Flights to Winona

Fall in love at first flight with your vacation to Winona by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Winona on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Winona, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Winona

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Winona with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the GWO airport.

What is the cheapest month to fly to Winona?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Winona are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Winona?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Winona.

What airport is best to fly into Winona?

When you’re planning your trip to Winona, convenience is the name of the game. Luckily, Winona University - Oxford Airport is nearby so you can deplane and get going on checking off everything on your Winona must-do list.

How much are flights to Winona?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Winona on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $261, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Winona?

The trick to saving a stack of cash on your flight to Winona? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $261 right now, why wait?

Winona Flight Information
Destination airport
Tupelo Regional
Destination airport IATA code
TUP
Roundtrip price
$122

Last Minute Hotel Deals 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
The price is $131 per night from Apr 28 to Apr 29
$131
includes taxes & fees
Apr 28 - Apr 29
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. ...
8.2/10 Very Good! (613 reviews)
"Stayed on our way to family. Very clean, bed was comfortable and breakfast was good!"

Reviewed on Apr 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
The price is $92 per night from Apr 21 to Apr 22
$92
includes taxes & fees
Apr 21 - Apr 22
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 ...
8/10 Very Good! (391 reviews)
"This was a decent place to get some sleep for the night as a stopover. Just know it could not be the quietest in the AM as folks (some pretty early) leave. Decent hot breakfast was a good surprise."

Reviewed on Apr 7, 2025

Americas Best Value Inn Winona
Relax Inn & Suites
Relax Inn & Suites
2 out of 5
328 US-82, Winona, MS
The price is $76 per night from Apr 27 to Apr 28
$76
includes taxes & fees
Apr 27 - Apr 28
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 ...
5.6/10 (39 reviews)
"Enjoyed my stay!"

Reviewed on Dec 9, 2024

Relax Inn & Suites
Holiday Inn Express & Suites Grenada by IHG
Holiday Inn Express & Suites Grenada by IHG
2.5 out of 5
1540 Sunset Dr, Grenada, MS
The price is $140 per night from May 7 to May 8
$140
includes taxes & fees
May 7 - May 8
Book a stay at this business-friendly hotel in Grenada. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (493 reviews)
"Great staff, ok facility. Breakfast staff hated being there. Ran out of egss and waited over 45 minutes before staff finally said they didn't have anymore."

Reviewed on Apr 2, 2025

Holiday Inn Express & Suites Grenada by IHG
Baymont by Wyndham Grenada
Baymont by Wyndham Grenada
2.5 out of 5
1575 Jamison Drive, Grenada, MS
The price is $89 per night from Apr 27 to Apr 28
$89
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Grenada. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Butler Hill Park and Bledsoe Park ...
6.2/10 (607 reviews)
"Great little place. Close to Walmart"

Reviewed on Mar 29, 2025

Baymont by Wyndham Grenada
OYO Hotel Grenada West
OYO Hotel Grenada West
2 out of 5
1451 Sunset Drive, Grenada, MS
The price is $83 per night from May 15 to May 16
$83
includes taxes & fees
May 15 - May 16
Stay at this hotel in Grenada. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Butler Hill Park and Bledsoe Park are located ...
6.4/10 (326 reviews)
No issues, but dated for you picky people
"Just fine for the price. Staff was honest (storm knocked out the power so I had to give $40 cash for deposit which they returned to me the next day at checkout.) Appliances are dated, rusted and worn, but everything functioned so no big deal to me. Most importantly, it was quiet and I slept ..."

Reviewed on Mar 26, 2025

OYO Hotel Grenada West
SureStay Plus Hotel by Best Western Greenwood
SureStay Plus Hotel by Best Western Greenwood
2.5 out of 5
635 Highway 82 W, Greenwood, MS
The price is $155 per night from Apr 23 to Apr 24
$155
includes taxes & fees
Apr 23 - Apr 24
Book a stay at this business-friendly hotel in Greenwood. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property ...
8/10 Very Good! (625 reviews)
"Room was clean and quiet. My neighbors were noisy, but I couldn’t hear them when in my room."

Reviewed on Apr 11, 2025

SureStay Plus Hotel by Best Western Greenwood
Hampton Inn & Suites Grenada
Hampton Inn & Suites Grenada
2.5 out of 5
1545 Jameson Dr, Grenada, MS
The price is $144 per night from Apr 17 to Apr 18
$144
includes taxes & fees
Apr 17 - Apr 18
Stay at this hotel in Grenada. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9/10 Wonderful! (632 reviews)
"I will be coming back"

Reviewed on Apr 11, 2025

Hampton Inn & Suites Grenada
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.