Winona Vacation Packages

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Your Winona Vacation

With one of our vacation 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 Center, 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 vacation on Expedia.

Winona Hotel Deals

Holiday Inn Express and Suites Winona North, an IHG Hotel
Holiday Inn Express and Suites Winona North, an IHG Hotel
2.5 out of 5
413 SE Frontage Road, Winona, MS
Fully refundable
The price is CA $194 per night from Jun. 1 to Jun. 2
CA $194
CA $211 total
includes taxes & fees
Jun 1 - Jun 2
8/10 Very Good! (529 reviews)
"Great place to stay very fast service"

Reviewed on May 10, 2024

Holiday Inn Express and Suites Winona North, an IHG Hotel
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 CA $130 per night from Jun. 5 to Jun. 6
CA $130
CA $142 total
includes taxes & fees
Jun 5 - Jun 6
8/10 Very Good! (322 reviews)
"Bathroom too small,,, i fell no saftey features 😒 otherwise everything was outstanding the staff was helpful and courteous wonderful,,, cannot stay again or recommend because of the bathroom"

Reviewed on May 14, 2024

Americas Best Value Inn Winona
Relax Inn & Suites
Relax Inn & Suites
2 out of 5
328 US-82, Winona, MS
The price is CA $96 per night from May 26 to May 27
CA $96
CA $105 total
includes taxes & fees
May 26 - May 27
5.2/10 (29 reviews)
"The prices are reasonable. It’s not the Hilton but it’s definitely worth a stay. Will be staying again."

Reviewed on Sep. 28, 2023

Relax Inn & Suites
See all 55 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winona vacation package cost?
We make it simple to explore the world, with Winona vacation packages starting from as low as . You’ll have the flexibility to bundle your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a couple of tours and experiences to your itinerary?
How do I get a cheap travel package to Winona?
Track down flights that fit your busy schedule, add a hotel room to your booking and watch the savings rack up with a Winona vacation package. It’s as easy as that! From hotels and flights to activities and rental cars, Expedia makes traveling cheaply a cinch. And with over 550 air carriers and 1,000,000 hotel options across the globe to select from, you’ll never be short of choice.
Where should I stay in Winona?
With interesting attractions like Winona Country Club and Montgomery County Performing Arts Center in this area, look for a hotel located near either of them. Middleton Cemetery is another Winona sight that visitors flock to.
What are the top hotels in Winona?
If this will be your first time in Winona, secure a room at Relax Inn & Suites or Americas Best Value Inn Winona. Both will make you feel at home and are favorites among many savvy travelers.
How far in advance should I book my Winona vacation?
Reserving your flight early with Expedia means one less thing to worry about. Most air carriers display prices up to 12 months prior to take off. Usually, this is the cheapest time to book. If circumstances have left you booking late, discount prices to Winona are still known to appear in the weeks leading up to departure.
What does an Expedia Winona travel package include?
It comes down to what you want. If you’re traveling alone, you might decide to combine hotels and flights. Bringing the whole family to Winona? A travel package including flights, hotels and rental cars might be a better fit. Expedia gives you the freedom and flexibility to tailor-make your travel package.
What should I know before booking a Winona travel package?
Booking all the parts of your trip together is one of the easiest ways to save. Bundle your car rentals, flights and hotels into a convenient little package. But your options don’t end at hotels. Expedia features all kinds of properties, including vacation rentals like beachfront villas and spacious residences. The list goes on!
Can I choose my airline with a Winona Expedia vacation package?
With a vacation package, you’re always in charge. Whether you’d prefer to fly to Winona in business or coach, simply pick from the available airline options. Expedia has access to over 550 airline partners across the world.
If I'm not able to travel, can I cancel my Winona vacation package?
Because we know life can be unpredictable, the answer is yes. To learn more, check out our Customer Service Portal. But generally speaking, if you’ve booked your package in the last 24 hours, you may be able to cancel or change it without penalty. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

Discover the most popular places to visit in Winona

Image for Winona Country Club

Winona Country Club

Enjoy a round of golf in Winona at Winona Country Club.

Winona Country Club
Image for Montgomery County Performing Arts Center

Montgomery County Performing Arts Center

You can get tickets for a performance at Montgomery County Performing Arts Center on your trip to Winona. Take in the theater scene while you're in the area.

Montgomery County Performing Arts Center
Image for Middleton Cemetery

Middleton Cemetery

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

Middleton Cemetery

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.