Winona Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Winona

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 S$176 per night from 7 Dec to 8 Dec
S$176
includes taxes & fees
7 Dec - 8 Dec
8/10 Very Good! (566 reviews)
"Everything was nice"

Reviewed on 5 Nov,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 S$118 per night from 25 Nov to 26 Nov
S$118
includes taxes & fees
25 Nov - 26 Nov
8/10 Very Good! (365 reviews)
"Very transient…… a hub for construction groups!"

Reviewed on 2 Nov,2024

Americas Best Value Inn Winona
Relax Inn & Suites
Relax Inn & Suites
2 out of 5
328 US-82, Winona, MS
The price is S$102 per night from 30 Nov to 1 Dec
S$102
includes taxes & fees
30 Nov - 1 Dec
5.4/10 (35 reviews)
"Ok"

Reviewed on 9 Nov,2024

Relax Inn & Suites
See all 47 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.

Frequently asked questions

How much does a Winona holiday package cost?
We make it simple to explore the world, with Winona holiday packages starting from as low as . You’ll have the flexibility to bundle your favourite 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 holiday package. It’s as easy as that! From hotels and flights to activities and rental cars, Expedia makes travelling 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 Centre 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 favourites among many savvy travellers.
How far in advance should I book my Winona holiday?
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 travelling 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 holiday rentals like beachfront villas and spacious residences. The list goes on!
Can I choose my airline with a Winona Expedia holiday package?
With a holiday 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 holiday 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.