
Winona Vacations
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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.
Discover the most popular places to visit in Winona
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.
Winona Hotel Deals

Holiday Inn Express and Suites Winona North by IHG
413 SE Frontage Road, Winona, MS
Fully refundable
$111 nightly
The price is $121 total per night from Sep 8 to Sep 9
$121 total
Sep 8 - Sep 9
Total includes taxes and fees
8.2/10 Very Good! (648 reviews)
"Great hotel"
Reviewed on Aug 8, 2025

Americas Best Value Inn Winona
301 SE Frontage Road, Winona, MS
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $108 total per night from Aug 12 to Aug 13
$108 total
Aug 12 - Aug 13
Total includes taxes and fees
8/10 Very Good! (420 reviews)
"Nothing fancy but a great location and nice breakfast options."
Reviewed on Aug 6, 2025

Relax Inn & Suites
328 US-82, Winona, MS
$70 nightly
The price is $76 total per night from Aug 12 to Aug 13
$76 total
Aug 12 - Aug 13
Total includes taxes and fees
5.6/10 (41 reviews)
"Met all of our needs: clean, quiet, frig, microwave, AC. Bed had unexpectedly luxurious and soft sheets."
Reviewed on Jul 23, 2025
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.