Historic Downtown Winona Vacations from $697
Book a Hotel + Flight or Car together to unlock savings
Your Historic Downtown Winona Vacation
Take all the stress out of planning your next break with a Historic Downtown Winona vacation package. Soak in the sounds and sights of this appealing neighborhood and experience everything it has to offer. Kick start your trip to Historic Downtown Winona by heading to nearby attractions such as Winona State University, St. Marys University of Minnesota and Sugar Loaf. Whatever your travel goals or budget, booking your dream Historic Downtown Winona vacation is quick and easy with Expedia.
The Latest Historic Downtown Winona Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Aspen Select
Kutzky Park
Price was $847, price is now $697 per person
$697
per person
Oct 18 - Oct 23
found 14 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Rochester (RST)
8.4/10 Very Good! (1,000 reviews)
Parking was tough. Other patrons parked horribly, so we were unable to find a parking spot. Thankfully, the person at the desk moved his vehicle and gave us his parking spot. Also the sliding door did not covered the entire bathroom opening. There was little to no air conditioning, and we were not able to adjust the temperature of our room.
Reviewed on Jul 22, 2026
The Towers At Kahler Grand Hotel
Downtown Rochester
Price was $1,769, price is now $1,428 per person
$1,428
per person
Oct 18 - Oct 23
found 14 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Rochester (RST)
9.6/10 Exceptional! (115 reviews)
Everyone was very helpful throughout our stay. Our Tower Suite was wonderful and amenities were great.
Reviewed on Jun 29, 2026
The Berkman
Folwell
Price was $1,130, price is now $965 per person
$965
per person
Oct 18 - Oct 23
found 14 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Rochester (RST)
9.6/10 Exceptional! (421 reviews)
Wonderful property with a few caveats. The amenities are great, and the location is ideal for St Mary’s. The apartment is large and parking safe and easy. That said, the bed is very hard and pillows aren’t great. The vents also hit directly on your face in the bed, so that was hard to get used to. I would stay again but only if I brought my own pillows and blankets
Reviewed on Jul 2, 2026
Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys
Kutzky Park
Price was $890, price is now $768 per person
$768
per person
Oct 18 - Oct 23
found 14 hours ago
Roundtrip non-stop flight included
Boise (BOI) to Rochester (RST)
9.2/10 Wonderful! (522 reviews)
Whenever we are in Rochester, we make sure to stay at the Homewood Suites. Always a consistent clean room and friendly staff.
Reviewed on Jul 23, 2026
Historic Downtown Winona Hotel Deals
Alexander Mansion Bed and Breakfast
274 East Broadway Winona MN
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Jul 30 to Jul 31
$109 total
Jul 30 - Jul 31
Total with taxes and fees
9.8/10 Exceptional! (528 reviews)
"Richard is the best host. He offered wine and a tour of the mansion after check-in. He left me Irish cream and chocolate in my bedroom. He also cooked the best 4-course gourmet breakfast in the morning! He is so sweet and kind! I will definitely be back again 😊"
Reviewed on Jul 24, 2026
Carriage House B&B
420 Main St Winona MN
$121 nightly
The price is $135 total per night from Jul 26 to Jul 27
$135 total
Jul 26 - Jul 27
Total with taxes and fees
9.6/10 Exceptional! (93 reviews)
"Delicious breakfast, charming property. Much more fun than a sterile hotel. Thank you!"
Reviewed on Jun 8, 2026
The Exchange 14 | Historic Bldg, Studio, Dwntwn
Winona MN
10/10 Exceptional! (14 reviews)
"Clean and quiet unit in a well-secured building. We’d stay here again."
Reviewed on Jul 4, 2026
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.
Stay near popular Historic Downtown Winona attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.