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Winona Holiday Rentals

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Holiday Rentals in Winona

Interior
Entire high-quality lodge well equipped and tranquil - See ALBINO deer!
10.0 out of 10, Exceptional, (64)
"This place is amazing, if you’re looking for a getaway in the middle of no where this is the place to go. The owners had some great recommendations and they even have a book with all the nearby places to checkout. I’ll be staying here again in the future!"
Entire high-quality lodge well equipped and tranquil - See ALBINO deer!
Exterior
Heritage hideaway-Secluded Log Cabin
10.0 out of 10, Exceptional, (325)
"We love our little “home away from home” you have provided. Thanks so much. We will be back."
Heritage hideaway-Secluded Log Cabin
Exterior
Root River Valley Cabin ~ Lanesboro, MN
10.0 out of 10, Exceptional, (258)
"Root River Valley Cabin is amazing, and the owners make it so easy to check in. It's always clean, well-appointed, and close to so many activities. I would recommend this cabin to anyone that is interested. Thank you again for another great trip!"
Root River Valley Cabin ~ Lanesboro, MN
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Property grounds
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
10.0 out of 10, Exceptional, (19)
"Rented this property for a girls weekend and everything was great! The house was clean, well stocked with everything and location was perfect!"
The BRD Nest Mississippi River views backdropped by majestic Minnesota bluffs
Exterior
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
10.0 out of 10, Exceptional, (106)
"This is my go-to spot for an annual trip to LaCrosse. It is nice to have a great place I can count on to be clean and comfortable!"
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse
Smart TV, DVD player, books
Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region
10.0 out of 10, Exceptional, (3)
"Everything was great and as expected. We showed up late in the dark and the lights were turned on for us. The place is quite large - there were 4 of us and room for more. Everything was clean and comfortable. Definitely would stay again."
Cozy 4 bedroom relax atmosphere enjoy beauty of bluff country driftless region
Property grounds
Newly remodeled, multifunctional, secluded retreat w/ views of Mississippi River
10.0 out of 10, Exceptional, (15)
"House/cabin had everything we needed... bedrooms, rec room, 2 bathrooms, 3 season porch and deck! We enjoyed using the fireplace, and the house location has a great view."
The price is NZ$673
includes taxes & fees
24 May - 25 May
Newly remodeled, multifunctional, secluded retreat w/ views of Mississippi River
Smart TV, fireplace
Secluded luxury House in the Hills w/king bed
10.0 out of 10, Exceptional, (14)
"We enjoyed the home tremendously-it was as beautiful as the photos and Tiffany was extremely accommodating. We appreciated all the details she saw to for our comfort and enjoyment. We would definitely ity stay again!"
Secluded luxury House in the Hills w/king bed
Exterior
Cabin on the Mississippi River
10.0 out of 10, Exceptional, (53)
"Very relaxing"
Cabin on the Mississippi River
Property grounds
Tamarack Point Homestead
10.0 out of 10, Exceptional, (11)
"This place was very clean and spacious. Well stocked kitchen and comfy furniture to relax on. It was very fun staying on the farm. I really enjoyed watching the chickens and rooster from the deck. The property was also decorated very nicely for the fall season. I would highly recommend staying here."
The price is NZ$203
includes taxes & fees
14 May - 15 May
Tamarack Point Homestead
Fridge, microwave, stovetop, dishwasher
'RiverSong' Waterfront La Crosse Home w/ Dock
10.0 out of 10, Exceptional, (65)
"Wonderful property! The host was wonderful and accommodating. The house has large showers, very organized and clean. The yard is meticulous kept cared for! We did some kayaking directly from the property that was not on the main channel so the currents did NOT sweep us away. We will definitely be back. HIGHLY RECOMMENDED AND A SUPER HOST!"
'RiverSong' Waterfront La Crosse Home w/ Dock
TV, fireplace
Toddy's Cabin
10.0 out of 10, Exceptional, (68)
"Cabin was very warm/welcoming. Had everything you would need. We loved our stay, while visiting our college kids in Winona. A+"
Toddy's Cabin
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
10.0 out of 10, Exceptional, (37)
"Awesome!"
The price is NZ$331
includes taxes & fees
15 May - 16 May
Logde sleeps 11 ...set up for exploring the Mississippi River or Driftless Area.
Property grounds
Marina getaway located on the back sloughs of the mighty Mississippi.
10.0 out of 10, Exceptional, (39)
"Our stay was ABSOLUTELY FABULOUS!"
Marina getaway located on the back sloughs of the mighty Mississippi.
Property grounds
Riverfront Twin Home
10.0 out of 10, Exceptional, (10)
"Place was great, clean, cute, accommodating."
The price is NZ$544
includes taxes & fees
14 May - 15 May
Riverfront Twin Home
Fridge, microwave, oven, stovetop
Spacious Pet Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Fireplace
10.0 out of 10, Exceptional, (6)
"The house met all of our expectations! Very spacious and clean! Beth was great to work with!"
Spacious Pet Friendly, Near UWL, Washer/Dryer, Fenced-In Yard, Fireplace
Smart TV
CONDO ON THE RIVER
10.0 out of 10, Exceptional, (2)
"Fun and spacious condo with multiple sleeping options. Our kids loved the bunk beds. Tons of space to spread out in the kitchen and living areas. Overall cleaniness was wonderful (although an update on bath towels is needed). Jason was a super communicative host. We'll definitely be back!"
CONDO ON THE RIVER
Beach
Studio apartment overlooking the beautiful Mississippi River
10.0 out of 10, Exceptional, (88)
"Great location and amenities. Works great for us to stay here and the owners are very friendly and accommodating"
Studio apartment overlooking the beautiful Mississippi River
Smart TV, DVD player, table football, ping pong
Country Charm Over River Valley And Horse Farm
10.0 out of 10, Exceptional, (25)
"Great place and location. Exactly as described. Communication from the host is great. We've stayed here twice now and would definitely come back. Great for a large group."
Country Charm Over River Valley And Horse Farm
Exterior
The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!
9.8 out of 10, Exceptional, (69)
"Loved the original furniture and decor. Signe was very available if I needed anything. We had a rehearsal dinner and everyone loved the home."
The Historic A.C. Carter House - River Romance on the La Crosse Historical Tour!
Don't see what you're looking for?
See all available 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.

Other types of properties in Winona you may be interested in

Lunch and dinner served, American cuisine
The Plaza Hotel & Suites Winona
3.0 star property
9.0 out of 10, Wonderful, (955)
"House keeping staff were very friendly and attentive, always available to assist and very pet friendly toward my dog! "
The price is NZ$259
includes taxes & fees
14 May - 15 May
The Plaza Hotel & Suites Winona
Exterior
AmericInn by Wyndham Winona
2.5 star property
9.0 out of 10, Wonderful, (645)
"Very clean and quiet place."
The price is NZ$229
includes taxes & fees
19 May - 20 May
AmericInn by Wyndham Winona
Lobby
Express Suites Riverport Inn & Suites
3.0 star property
8.4 out of 10, Very good, (1007)
"The tv in the room didn’t work but other than that, it was a good stay. "
The price is NZ$204
includes taxes & fees
16 May - 17 May
Express Suites Riverport Inn & Suites
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Winona holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Winona. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Winona. Seeing all the best attractions is bound to make you fall in love with Winona. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Winona short-term rentals, that won’t be hard to do.

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.

How many holiday rentals are there in Winona?

Expedia has 10 holiday rentals for your stay in Winona.

What can I see and do in Winona?

Enjoy the outdoors at Great River Bluffs State Park and Mississippi River, or simply take in cultural attractions like Minnesota Marine Art Museum and Winona County Historical Society. While here, Lake Lodge Recreation Center and Lake 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.

Recent reviews of Winona properties
Expedia verified reviews