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Winona Holiday Rentals

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Holiday Rentals in Winona

The Broadway Exchange

10.0 out of 10, Exceptional, (27)
"The owners are very timely in their communication. The home is always clean and has things to do (books, games) and information about what is going on around town. While my kids all have their own space, the house lends itself to hanging out and enjoying each other's company! I love that house is updated, but still retains some original craftmanship and charm."
The Broadway Exchange

Charming Brick Farmhouse with a Touch of Elegance. -Winona

10.0 out of 10, Exceptional, (124)
"This property is amazing! By far the best VRBO property I have had the pleasure to stay."
The price is AU$706
includes taxes & fees
17 June - 18 June
Charming Brick Farmhouse with a Touch of Elegance. -Winona

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!

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

10.0 out of 10, Exceptional, (7)
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

Creekside Cabin Getaway

9.4 out of 10, Exceptional, (104)
"It was a peaceful place beautiful cabin I would definitely recommend "
Creekside Cabin Getaway

Family friendly in the peaceful heart of town

10.0 out of 10, Exceptional, (93)
"We had a lovely and comfortable stay for Thanksgiving. Walkable or very short drive to the sights and amenities of Winona! "
Family friendly in the peaceful heart of town

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 AU$252
includes taxes & fees
16 June - 17 June
Big River Escape Riverside Cabins

Downtown La Crosse Modern Flat

9.4 out of 10, Exceptional, (56)
"The place was great and the location was very convenient, especially if you wanted to stay up partying into the night (as advertised). "
The price is AU$498
includes taxes & fees
15 June - 16 June
Downtown La Crosse Modern Flat

Toddy's Cabin

10.0 out of 10, Exceptional, (106)
"Beautiful place, my family and I would do diffidently stay here again! "
Toddy's Cabin

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

9.8 out of 10, Exceptional, (23)
"Loved the history of the property plus the modern amenities and updates!"
The price is AU$358
includes taxes & fees
15 June - 16 June
Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion

Bluffside cottage with gorgeous river views

10.0 out of 10, Exceptional, (27)
"So cute/quiet/clean with gorgeous views of the river!"
Bluffside cottage with gorgeous river views

Root River Valley Cabin ~ Lanesboro, MN

10.0 out of 10, Exceptional, (307)
"It was comfortable, relaxing, and quiet. A nice location. "
Root River Valley Cabin ~ Lanesboro, MN

Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

9.8 out of 10, Exceptional, (7)
"Excellent communication from our host! He was very accommodating to my last minute requests (early arrival and ski team dinner). The entire house was immaculate. We loved the view, especially in the morning with coffee in the seating area off of the kitchen. I wish that we had more time to spend in the game room or relaxing in front of the fireplace. Thank you for a wonderful weekend!"
Charming 3-bedroom house with WiFi and AC in beautiful La Crosse

Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

9.8 out of 10, Exceptional, (27)
"This was a great place to stay that was close to UWL and downtown. Loved having the room to move around in the house vs a hotel room. Also, loved the outdoor area. "
The price is AU$211
includes taxes & fees
13 July - 14 July
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

The Hen House Retreat - A Comfortable Place to Roost

9.6 out of 10, Exceptional, (75)
"Quaint, cozy, clean and thoughtfully stocked. A surprise: a small shop of handmade jewelry."
The price is AU$309
includes taxes & fees
23 June - 24 June
The Hen House Retreat - A Comfortable Place to Roost

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

10.0 out of 10, Exceptional, (62)
"We had a great stay! Perfect quiet place near everything!"
Marina getaway located on the back sloughs of the mighty Mississippi.

Great 1 Bedroom unit with easy access to everything

9.6 out of 10, Exceptional, (50)
"Very quiet and cozy and close to convention center"
The price is AU$356
includes taxes & fees
10 July - 11 July
Great 1 Bedroom unit with easy access to everything

Secluded Home - Views of Mississippi River remote location 15 min from La Crosse

10.0 out of 10, Exceptional, (150)
"Great views, very clean, fun activities"
Secluded Home - Views of Mississippi River remote location 15 min from La Crosse

Riverfront Twin Home

10.0 out of 10, Exceptional, (26)
"Nice place to stay. Great location. "
The price is AU$479
includes taxes & fees
15 June - 16 June
Riverfront Twin Home

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

10.0 out of 10, Exceptional, (33)
"Very good stay. Excellent accommodateions.great overall"
The price is AU$629
includes taxes & fees
15 June - 16 June
Spacious & Immaculate Dog-Friendly Gem, Near UWL, Washer/Dryer & Fire Pit!
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?

Comfort & Elegance in a Historic La Crosse, Wisconsin Mansion: This holiday home rental outside of Winona has air conditioning and laundry facilities 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.

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 Lodge Recreation Center and Lake Park, or simply take in cultural attractions like Minnesota Marine Art Museum and Pickwick Mill. While here, Great River Bluffs State Park and Mississippi River 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.