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Winona Vacation Rentals

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In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Winona

Family Cottage, Park View | Private kitchen
Big River Escape Parkside Bungalow

Big River Escape Parkside Bungalow

3.0 star property
Winona
10.0 out of 10, Exceptional, (1)
"We had a wonderful time and would defiinitely stay again. "
United States
Julie
$218 nightly
The price is $243
Dec 7 - Dec 8
Total with taxes and fees
Big River Escape Parkside Bungalow
Exterior
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

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

Historic Downtown Winona
10.0 out of 10, Exceptional, (20)
"It was a wonderful stay with a nice and helpful host! Place was clean and well maintained. "
United States
enforcer1219
$170 nightly
The price is $183
Dec 8 - Dec 9
Total with taxes and fees
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO
Fridge, microwave, oven, stovetop
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

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.
$286 nightly
The price is $308
Dec 6 - Dec 7
Total with taxes and fees
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
Exterior
Charming Brick Farmhouse with a Touch of Elegance. -Winona

Charming Brick Farmhouse with a Touch of Elegance. -Winona

Winona
10.0 out of 10, Exceptional, (136)
"Beautiful home! Close to SMU campus. "
United States
Lucy M.
$372 nightly
The price is $400
Dec 7 - Dec 8
Total with taxes and fees
Charming Brick Farmhouse with a Touch of Elegance. -Winona
Cabin, 2 Bedrooms | Private kitchen | Full-size fridge, microwave, oven, stovetop
Big River Escape Riverside Cabins

Big River Escape Riverside Cabins

3.0 star property
Cochrane
9.2 out of 10, Wonderful, (38)
"Beautiful stay"
United States
IVETTE
$103 nightly
The price is $109
Dec 7 - Dec 8
Total with taxes and fees
Big River Escape Riverside Cabins
Property grounds
Tamarack Point Homestead

Tamarack Point Homestead

Arcadia
10.0 out of 10, Exceptional, (31)
"Cozy place, had everything we needed, it was quiet and peaceful! Highly recommend."
United States
Luke H.
$111 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
Tamarack Point Homestead
Smart TV
Hokah Ohana House: Historic charm, Modern updates

Hokah Ohana House: Historic charm, Modern updates

Hokah
10.0 out of 10, Exceptional, (32)
"Perfect place for 4 of us to stay while visiting for a wedding. "
United States
Jeff W.
$173 nightly
The price is $185
Dec 7 - Dec 8
Total with taxes and fees
Hokah Ohana House: Historic charm, Modern updates
Fridge, microwave, oven, stovetop
Downtown La Crosse Modern Flat

Downtown La Crosse Modern Flat

Historic Downtown La Crosse
9.4 out of 10, Exceptional, (63)
"The place is right in the middle of shops, restaurants, and just a short walk from the river and park"
United States
Adam C.
$265 nightly
The price is $305
Dec 7 - Dec 8
Total with taxes and fees
Downtown La Crosse Modern Flat
Fridge, microwave, oven, stovetop
Big River Inn - 3 bedroom apartment in Alma

Big River Inn - 3 bedroom apartment in Alma

Alma
8.6 out of 10, Excellent, (14)
"Great place in the heart of Alma"
United States
Kevin B.
$206 nightly
The price is $229
Dec 7 - Dec 8
Total with taxes and fees
Big River Inn - 3 bedroom apartment in Alma
Exterior
Treehouse Cabin in the Bluff Woodlands North

Treehouse Cabin in the Bluff Woodlands North

Elba
9.6 out of 10, Exceptional, (9)
"Great relaxing place! "
United States
James H.
$153 nightly
The price is $165
Dec 7 - Dec 8
Total with taxes and fees
Treehouse Cabin in the Bluff Woodlands North
Terrace/patio
Treehouse Cabin in the Bluff Woodlands

Treehouse Cabin in the Bluff Woodlands

Elba
9.8 out of 10, Exceptional, (15)
"Beautiful area enjoyed our stay immensely"
United Kingdom
I.M l.
$153 nightly
The price is $165
Dec 7 - Dec 8
Total with taxes and fees
Treehouse Cabin in the Bluff Woodlands
Fridge, microwave, oven, stovetop
Downtown La Crosse Modern Flat

Downtown La Crosse Modern Flat

Historic Downtown La Crosse
9.8 out of 10, Exceptional, (47)
"It was lovely and we really enjoyed being able to walk everywhere and easy access toThe downrown"
United States
Lisa T.
$290 nightly
The price is $334
Dec 7 - Dec 8
Total with taxes and fees
Downtown La Crosse Modern Flat
Dining
Warm and Cozy Upstairs Apartment

Warm and Cozy Upstairs Apartment

Caledonia
9.4 out of 10, Exceptional, (14)
"Clean and cozy! Loved our stay!"
United States
Sarah
$153 nightly
The price is $163
Dec 7 - Dec 8
Total with taxes and fees
Warm and Cozy Upstairs Apartment
Exterior detail
The Hen House Retreat - A Comfortable Place to Roost

The Hen House Retreat - A Comfortable Place to Roost

Highland
9.8 out of 10, Exceptional, (87)
"Very nice perfect for us, would rent again!"
United States
Mitchell G.
$186 nightly
The price is $200
Dec 7 - Dec 8
Total with taxes and fees
The Hen House Retreat - A Comfortable Place to Roost
Exterior
River City Apartment #1 with flex space

River City Apartment #1 with flex space

Historic Downtown La Crosse
8.8 out of 10, Excellent, (3)
"Great property, great location! Very clean and walkable to most places downtown and to the river and riverboat. By great restaurants and so much going on in LaCrosse. Host very responsive. Obviously you need to climb stairs as it is above a business. Also LaCrosse has a lot of parking rules but very easy and cheap to stay in close ramps. Would definitely visit again and recommend! One more thing, this weekend was the 61st anniversary of the banjo festival and if you like that type of music,...
United States
Julie K.
$260 nightly
The price is $299
Dec 7 - Dec 8
Total with taxes and fees
River City Apartment #1 with flex space
Property grounds
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard

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

Northside
9.8 out of 10, Exceptional, (46)
"Wonderful stay, super cozy, perfect for a getaway "
United States
Katie C.
$143 nightly
The price is $164
Dec 14 - Dec 15
Total with taxes and fees
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
Property grounds
French Island w/Hot Tub, Kayak, Lake View, EV

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

La Crosse
10.0 out of 10, Exceptional, (19)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
$290 nightly
The price is $314
Dec 8 - Dec 9
Total with taxes and fees
French Island w/Hot Tub, Kayak, Lake View, EV
Interior
Suite #3 - Spacious King Suite -Mississippi River

Suite #3 - Spacious King Suite -Mississippi River

Fountain City
8.8 out of 10, Excellent, (5)
"Beautiful historic home. Enjoyed the lication."
United States
Kelly B.
$105 nightly
The price is $111
Dec 7 - Dec 8
Total with taxes and fees
Suite #3 - Spacious King Suite -Mississippi River
TV, fireplace
Riverfront Twin Home

Riverfront Twin Home

La Crosse
10.0 out of 10, Exceptional, (42)
"Great place to stay! Had everything we needed!"
United States
Angie C.
$265 nightly
The price is $305
Dec 7 - Dec 8
Total with taxes and fees
Riverfront Twin Home
Private kitchen
Jake's Place

Jake's Place

Powell-Poage-Hamilton
9.8 out of 10, Exceptional, (8)
"Great place, great location. Very clean & practical! "
United States
Cori C.
$254 nightly
The price is $292
Dec 7 - Dec 8
Total with taxes and fees
Jake's Place
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

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

10/10 Excellent
"Room was clean staff was frendly and helpfull"
Glenda 2-night trip
Posted 4 days ago
Express Suites Riverport Inn & Suites

Find out more about Winona

Everything you need to know about Winona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winona vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winona in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $109 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winona?

Yes, there are vacation rentals near the most popular sights in Winona, or you can choose a more secluded option if you'd like a relaxing place to 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 vacation rentals that Winona has to offer?

Waterfront Home with HOT TUB, Large Dock, Game Room, Movie Theater : Visitors give good reviews to this Winona vacation home rental, which offers a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Our travelers also rate Spacious house w/hot tub & river view as a favorite home for rent in Winona.

How many vacation rentals are there in Winona?

Expedia has 14 vacation 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 Winona County Historical Society. While here, Great River Bluffs State Park and Mississippi River are other places worth a visit.

What are vacation rentals like in Winona?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Winona. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.