Winona Holidays

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Your Winona Holiday

With one of our holiday 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 Centre, 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 holiday on Expedia.

Winona Essential Information

Language
English
Currency
U.S dollars
Population
4,400
Max Temp Winter
13ºC
Max Temp Summer
32ºC
Top Sights
Montgomery County Performing Arts Centre, Winona Country Club and Middleton Cemetery

Our pick of the best 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
Stay at this business-friendly hotel in Winona. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
8.2/10 Very Good! (628 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
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 ...
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
Charming 3-bedroom barn in quaint Winona with AC
Charming 3-bedroom barn in quaint Winona with AC
Winona, MS
Stay at this holiday home in Winona. Enjoy laundry facilities and air conditioning. Popular attractions Montgomery County Performing Arts Center and Winona - ...
Charming 3-bedroom barn in quaint Winona with AC
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Winona travel package cost?
Handcraft your Winona travel package from as low as . Choose from any combination of hotels, flights and rental cars to create the escape you've long been dreaming about. Remember to add on some activities and experiences!
If I'm not able to travel, can I cancel my Winona travel package?
Don't worry if you're rethinking your Winona travel package --- it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your airline, hotel or car rental company. We totally get that life can sometimes throw you a curveball, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Winona?
Booking a Winona travel package with Expedia is one of the best ways to save. We have more than 550 air carriers and 1,000,000 hotel options around the world. With such an awesome range to choose from, you'll have no trouble creating your dream trip.
Does Expedia offer Book Now, Pay Later Winona holidays?
Expedia has partnered with online lender Klarna to make booking your next getaway a little easier on the wallet. Paying in instalments means you can spread the costs of your next adventure, leaving you with more cash to play with while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that suits your budget. Consider these flexible payment options:
  • Pay monthly holidays: If paying small amounts each month is something that would work for you, Klarna can help. Paying in convenient monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday in multiple transactions.
  • Low deposit holidays: Clicking on the "book now" button is easier with this option. Just put down a small deposit on your escape and then get on your way.

Where should I stay in Winona?
With lots to discover in Winona, we suggest you book a hotel near its attractions. Montgomery County Performing Arts Centre, Winona Country Club and Middleton Cemetery are some popular ones to add to your must-see list.
What are the top hotels in Winona?
Get your escape off to a fantastic start by booking a room at Holiday Inn Express and Suites Winona North, an IHG Hotel. It's one of most sought-after hotels in Winona. Another welcoming option is Americas Best Value Inn Winona.
How far in advance should I book my Winona holiday?
It all depends on the air carrier, but you can normally compare international airfares on Expedia up to a year in advance. While it's generally a good idea to book ahead of time, lucky travellers occasionally nab a cheaper seat just weeks before the date of departure.
What does an Expedia Winona travel package include?
Expedia has all you need to organise your Winona trip, but how you structure your package is entirely up to you. Pick from any combination of flights, rental cars and hotels. After some activities to keep you entertained? Once you've made your booking, you can add them on too. No matter your style, there's a deal to match your needs.
What should I know before booking a Winona travel package?
Our prices are always low. However, you'll enjoy even better deals when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and a great range of choice.
Can I choose my airline with a Winona Expedia travel package?
Expedia offers access to more than 550 partner airlines worldwide, so you sure can! Just choose the carrier that suits you and create your ideal Winona trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.