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Top Holiday Rentals in Winona

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (126)
"This property is amazing! By far the best VRBO property I have had the pleasure to stay."
The price is £362
includes taxes & fees
9 Jul - 10 Jul
Charming Brick Farmhouse with a Touch of Elegance. -Winona

Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

10.0 out of 10, Exceptional, (9)
"Great little house close to several antique and thrift shops! "
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater

2.0 star property
10.0 out of 10, Exceptional, (7)
"Very large, nice place to stay for all ages"
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater

This AMAZING river getaway is PERFECT for YOU! Private deck, grill & fire pit!

9.6 out of 10, Exceptional, (4)
"Unique location close to downtown Winona-perfect for our family gathering!"
This AMAZING river getaway is PERFECT for YOU! Private deck, grill & fire pit!

Big River Escape Riverside Cabins

3.0 star property
9.0 out of 10, Wonderful, (30)
"Very, nice and quiet stay. Would definitely be coming back. The local pub & gas station was very welcoming and friendly to us for not being from the area. "
The price is £97
includes taxes & fees
5 Aug - 6 Aug
Big River Escape Riverside Cabins

Heritage hideaway-Secluded Log Cabin

10.0 out of 10, Exceptional, (383)
"We had a very lovely weekend stay at this cabin. It was very easy to access many different state parks from the area and the property itself was very beautiful. "
Heritage hideaway-Secluded Log Cabin

Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

10.0 out of 10, Exceptional, (36)
"Very good stay. Excellent accommodateions.great overall"
The price is £313
includes taxes & fees
16 Jul - 17 Jul
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

9.8 out of 10, Exceptional, (27)
"Loved the history of the property plus the modern amenities and updates!"
The price is £172
includes taxes & fees
10 Jul - 11 Jul
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

10.0 out of 10, Exceptional, (140)
"3 couples enjoying a weekend away :) "
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

Riverfront Twin Home

10.0 out of 10, Exceptional, (26)
"Nice place to stay. Great location. "
The price is £231
includes taxes & fees
10 Jul - 11 Jul
Riverfront Twin Home

Root River Valley Cabin ~ Lanesboro, MN

10.0 out of 10, Exceptional, (313)
"Quiet, secluded, inviting and comfortable. Wonderful location for a short get away. "
Root River Valley Cabin ~ Lanesboro, MN

Marina getaway located on the back sloughs of the mighty Mississippi.

10.0 out of 10, Exceptional, (63)
"We had a great stay! Perfect quiet place near everything!"
Marina getaway located on the back sloughs of the mighty Mississippi.

Newly remodeled, multifunctional, secluded retreat w/ views of Mississippi River

10.0 out of 10, Exceptional, (39)
"We enjoyed our stay at the "
Newly remodeled, multifunctional, secluded retreat w/ views of Mississippi River

River Rambler

9.6 out of 10, Exceptional, (10)
"Great experience, had everything we needed and wanted! Hostess was excellent!"
River Rambler

Great 1 Bedroom unit with easy access to everything

9.6 out of 10, Exceptional, (52)
"We stayed one night at this property. Lots of space and very clean. Location is ideal; breakfast at The Damn Tasty is a must and right around the corner! "
The price is £171
includes taxes & fees
8 Jul - 9 Jul
Great 1 Bedroom unit with easy access to everything

The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air

9.8 out of 10, Exceptional, (28)
"A perfect place to gather after a day of sight seeing. "
The Tritsch House -Beautifully Restored Queen Anne Alma WI - Central Air

French Island w/Hot Tub, Kayak, Lake View, EV

10.0 out of 10, Exceptional, (14)
"Very nice place. Great area."
French Island w/Hot Tub, Kayak, Lake View, EV

Ridgetop Retreat Tiny Home, Dakota MN

2.0 star property
9.6 out of 10, Exceptional, (4)
"The Tiny House is what the name implies but there was ample space for 2 adults, 1 teenager and our dog. Everything is like new. Lots of outdoor space and a great walking trail. Would recommend and stay here again."
The price is £104
includes taxes & fees
8 Jul - 9 Jul
Ridgetop Retreat Tiny Home, Dakota MN

Warm and Cozy Upstairs Apartment

9.4 out of 10, Exceptional, (11)
"Clean and cozy! Loved our stay!"
The price is £122
includes taxes & fees
8 Jul - 9 Jul
Warm and Cozy Upstairs Apartment

Toddy's Cabin

10.0 out of 10, Exceptional, (109)
"Beautiful place, my family and I would do diffidently stay here again! "
Toddy's Cabin
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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Frequently asked questions

Can I find holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay. The riverfront and museums are just a few reasons why tourists like Winona. Make sure you have time to check out the gardens and churches during your trip.

What are some of the best holiday rentals that Winona has to offer?

Charming Brick Farmhouse with a Touch of Elegance. -Winona: This highly rated holiday home rental in Winona offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Winona?

Expedia has 13 holiday rentals for your stay in Winona.

What can I see and do in Winona?

Enjoy the outdoors at Lake Park and Mississippi River, or simply take in cultural attractions like Minnesota Marine Art Museum and Winona County Historical Society. While here, Winona County Courthouse and Great River Bluffs State Park are other places worth a visit.

What are holiday rentals like in Winona?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winona. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for families.