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Holiday Rentals in Winona

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Holiday Rentals in Winona

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

2.0 star property
Winona
10.0 out of 10, Exceptional, (9)
"Wonderful property- there were so many fun things to do and loved the location."
United States
Sean J.
Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater

Charming Brick Farmhouse with a Touch of Elegance. -Winona

Winona
10.0 out of 10, Exceptional, (134)
"It was very comfortable house to stay in snd share our time together. "
United States
Peggy M.
The price is €403
includes taxes & fees
17 Nov - 18 Nov
Charming Brick Farmhouse with a Touch of Elegance. -Winona

Big River Escape Parkside Bungalow

3.0 star property
Winona
The price is €210
includes taxes & fees
11 Nov - 12 Nov
Big River Escape Parkside Bungalow

Creekside Cabin Getaway

Winona
9.4 out of 10, Exceptional, (113)
"The property was beautiful and relaxing!"
United States
melanie
Creekside Cabin Getaway

Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

Winona
10.0 out of 10, Exceptional, (24)
"The home was perfect for 3 adults needing 3 bedrooms in a quiet location in a safe neighborhood! Very cute house, nicely appointed with everything we needed (and more)!"
United States
LeAnne L.
The price is €269
includes taxes & fees
9 Nov - 10 Nov
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

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

Winona
9.8 out of 10, Exceptional, (6)
"The property was exactly as described in the listing and had all of the needs required to cook a simple meal at the house. We loved the 60's decor and all of the cozy blankets all over the house. It was perfect for late night/early morning chats together in the living room."
United States
Misty B.
This AMAZING river getaway is PERFECT for YOU! Private deck, grill & fire pit!

1 Mi to Downtown: Welcoming Winona Duplex

3.5 star property
Winona
1 Mi to Downtown: Welcoming Winona Duplex

Big River Escape Riverside Cabins

3.0 star property
Cochrane
9.2 out of 10, Wonderful, (38)
"The staff went above and beyond my expectations!!!!!! The camper was clean and comfortable. Great location for a get away. Would HIGHLY recommend! "
United States
Kerri
The price is €120
includes taxes & fees
12 Nov - 13 Nov
Big River Escape Riverside Cabins

Toddy's Cabin

Trempealeau
10.0 out of 10, Exceptional, (126)
"Rustic cabin with everything you need for a great stay!"
United States
Anonymous traveller
Toddy's Cabin

River Front Property

Northside
9.8 out of 10, Exceptional, (104)
"Location was perfect! Patio was exceptional and had all the amenities we could ever need. Host had info for activities to do in the area. Location was close to the boat ramps. Would love to stay again! "
United States
Mike H.
River Front Property

Cabin on the Mississippi River

Trempealeau
10.0 out of 10, Exceptional, (89)
"This cabin is right on the river and the view is wonderful. There is always trains near the river, but the sound isnt an issue here. We will definitely rent again."
United States
Steve K.
Cabin on the Mississippi River

Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

La Crosse
10.0 out of 10, Exceptional, (41)
"Overall was a great experience. The property manager communication was great. The property was clean and well-kept."
United States
Bill H.
Premium 3BR 3BA with Hot Tub & Pool, near all of LaCrosse's Top Rated Activities

Root River Valley Cabin ~ Lanesboro, MN

Lanesboro
10.0 out of 10, Exceptional, (335)
"Wonderful cabin on Root River Bike trail! We loved the space and location! So cozy and quiet for our family weekend! My favorite was reading on the porch while sitting in the hanging swing! "
United States
Ramona M.
Root River Valley Cabin ~ Lanesboro, MN

Modern condo near the heart of downtown La Crosse and all it has to offer!

Historic Downtown La Crosse
9.8 out of 10, Exceptional, (61)
"Very nice property!"
United States
Tori B.
Modern condo near the heart of downtown La Crosse and all it has to offer!

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

Powell-Poage-Hamilton
10.0 out of 10, Exceptional, (155)
"Really enjoyed our stay here. Stayed just a couple nights and everything was clean, comfortable and cozy. Location was perfect for our needs. Would highly recommend.."
United States
Mary B.
8th Street Blues! 3 Bed, 2 Bath near downtown LaCrosse

Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples

La Crosse
10.0 out of 10, Exceptional, (109)
"Nice open space for cooking/family time and kids loved playing school/writing on chalk board!"
United States
Sara D.
Wilson Schoolhouse Inn----- Ideal For Family Gatherings Or 2-3 Couples

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

Northside
9.8 out of 10, Exceptional, (45)
"Wonderful stay, super cozy, perfect for a getaway "
United States
Katie C.
The price is €180
includes taxes & fees
22 Nov - 23 Nov
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

Downtown La Crosse Modern Flat

Historic Downtown La Crosse
9.2 out of 10, Wonderful, (62)
"Beautiful property! Enjoyed every minute of our stay and will for sure be back!"
United States
Molly
Downtown La Crosse Modern Flat

A fully remodeled home overlooking Mississippi River in a charming river town!

Downtown Trempealeau
9.8 out of 10, Exceptional, (64)
"Second time we have stayed here. We love the house and location. Very accommodating and beautifully renovated "
United States
Lori
A fully remodeled home overlooking Mississippi River in a charming river town!

Heritage hideaway-Secluded Log Cabin

Chatfield
10.0 out of 10, Exceptional, (404)
"We loved the space for indoor/outdoor games as a family, quiet nooks to read, and the kitchen/dining area for sharing meals. It was close enough to get to our daily activities in nearby towns, but so quiet and cozy when we wanted to relax!"
United States
Melissa H.
Heritage hideaway-Secluded Log 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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Top Winona Hotel Reviews

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as €120 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater : This highly rated holiday home rental in Winona offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Winona?

Expedia has 14 holiday rentals for your stay in Winona.

What can I see and do in Winona?

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