A river flowing through a forest with autumn-colored trees.

Winona County Vacation Rentals

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Top Cities in Winona County

A stone wall with a hole, overlooking a river and a town.
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Winona

Winona
A field of tall, golden grasses with a lake and distant mountains in the background.
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La Crescent

La Crescent

Our top choices for Winona County vacation rentals

A wooden cabin with a porch, two chairs, and a door.

1. Tiny Treehouse Cabin | Bluff Woodlands #2

Tiny Treehouse Cabin | Bluff Woodlands #2
Elba
9.8 out of 10, Exceptional, (17 reviews)
"Beautiful area enjoyed our stay immensely"
United Kingdom
I.M l.
The price is CA $168
CA $273 total
includes taxes & fees
Oct 5 - Oct 6
Tiny Treehouse Cabin | Bluff Woodlands #2
A bunk bed room with a window view, a ceiling fan, and a TV.

2. Ridgetop Retreat Tiny Home, Dakota MN

Ridgetop Retreat Tiny Home, Dakota MN
Dakota
9.4 out of 10, Exceptional, (10 reviews)
"Everything was perfect for our one night stay… owner was very helpful and easy to reach. Only small issue was that it was a little difficult to get up and down the ladders to the lofted beds.. but now that we know what to expect, we would definitely consider staying here again!"
United States
Jessica W.
The price is CA $167
CA $210 total
includes taxes & fees
Oct 18 - Oct 19
Ridgetop Retreat Tiny Home, Dakota MN
Two wooden cabins elevated on stilts in a forest, with outdoor seating and hammocks.

3. Tiny Treehouse Cabin | Bluff Woodlands #1

Tiny Treehouse Cabin | Bluff Woodlands #1
Elba
9.6 out of 10, Exceptional, (10 reviews)
"Great area a place to stay. "
United States
Paul T.
The price is CA $183
CA $291 total
includes taxes & fees
Oct 5 - Oct 6
Tiny Treehouse Cabin | Bluff Woodlands #1
A two-story house with a wooden staircase leading to a yellow door, a brick wall, and a window with a white frame.

4. Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons

Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
Historic Downtown Winona
10.0 out of 10, Exceptional, (32 reviews)
"Very clean, great hosts, fully equipped we everything we needed. "
United States
Amy B.
The price is CA $214
CA $271 total
includes taxes & fees
Oct 5 - Oct 6
Charming 1BR house with WiFi, AC, Private Patio + Cruiser Bikes & Grill Add-Ons
A modern apartment with a staircase, a dining area, and a living space.

5. 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, (34 reviews)
"A charming place to stay with a spacious primary bedroom, laundry room, and living areas. The backyard patio is a perfect place for a morning coffee and a quiet evening. We would definitely rebook on our next visit."
United States
Mainul
The price is CA $333
CA $411 total
includes taxes & fees
Oct 5 - Oct 6
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
A living room with a television, sofa, coffee table, and shelves with decorative items.

6. Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (36 reviews)
"A beautiful comfortable welcoming home!"
United States
Jocelyn R.
The price is CA $192
CA $305 total
includes taxes & fees
Oct 5 - Oct 6
Vintage Lustron Home Piece of History
A patio with two chairs and a table, a fire pit, a wooden fence, and a shed in the background.

7. Parkside Pet Friendly Bungalow

Parkside Pet Friendly Bungalow
Winona
8.0 out of 10, Very good, (2 reviews)
"Parkview is a quaint bungalow one block off the Lake. Easy access to Downtown, Winona State and recreation. Lovely back yard and front porch. Plenty of party in front and back. Definitely will stay again."
United States
Mary T.
The price is CA $294
CA $364 total
includes taxes & fees
Oct 5 - Oct 6
Parkside Pet Friendly Bungalow
A round glass table with two wicker chairs, a bottle, and two glasses of red wine on a metal tray.

8. Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN

Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
Winona
10.0 out of 10, Exceptional, (150 reviews)
"Absolutely amazing! So much charm and space…could definitely stay here again!"
United States
Lynn B.
The price is CA $417
CA $710 total
includes taxes & fees
Oct 5 - Oct 6
Village House Inn A Charming Brick Farmhouse with a Touch of Elegance -Winona MN
A wooden cabin with a porch, two chairs, and a door.

9. Three Treehouse Cabins in the Bluff Woodlands

Three Treehouse Cabins in the Bluff Woodlands
Elba
The price is CA $534
CA $802 total
includes taxes & fees
Oct 5 - Oct 6
Three Treehouse Cabins in the Bluff Woodlands
A covered deck with outdoor seating, surrounded by a forested area.

10. Tiny Treehouse Cabin | Bluff Woodlands #3

Tiny Treehouse Cabin | Bluff Woodlands #3
Elba
10.0 out of 10, Exceptional, (13 reviews)
"My family of 4 had a wonderful stay!"
United States
Josh S.
The price is CA $183
CA $291 total
includes taxes & fees
Oct 5 - Oct 6
Tiny Treehouse Cabin | Bluff Woodlands #3
A compact RV kitchen with wooden cabinets, a stove, and a dining area with a bench.

11. Big River Escape Coyote Camper #1

Big River Escape Coyote Camper #1
Buffalo City
10.0 out of 10, Exceptional, (2 reviews)
"Awesome as usual "
United States
Matthew B.
The price is CA $168
CA $207 total
includes taxes & fees
Oct 5 - Oct 6
Big River Escape Coyote Camper #1
A calm river with boats docked on the right, a clear sky, and dense trees on the left.

12. 2-bedroom house boat in beautiful La Crosse with AC comfort

2-bedroom house boat in beautiful La Crosse with AC comfort
West La Crosse
10.0 out of 10, Exceptional, (14 reviews)
"Excellent stay. Very relaxing and we caught some fish right off the back of the houseboat!"
United States
Tom B.
The price is CA $214
CA $397 total
includes taxes & fees
Oct 13 - Oct 14
2-bedroom house boat in beautiful La Crosse with AC comfort
A field of lavender with a path leading through it.

13. Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (46 reviews)
"Brady was very prompt and the stay exceeded expectations We plan to stay again very soon! Thank you, Brady!"
United States
Josias F.
The price is CA $130
CA $167 total
includes taxes & fees
Oct 12 - Oct 13
Tamarack Point Homestead
A spacious living room with a brown sofa, a round coffee table, and a patterned rug. There is a ceiling fan, a dining area with chairs, and a staircase leading to another level.

14. Hokah Ohana House: Historic charm, Modern updates

Hokah Ohana House: Historic charm, Modern updates
Hokah
10.0 out of 10, Exceptional, (39 reviews)
"Very comfortable and had everything you need to feel at home!"
United States
David R.
The price is CA $119
CA $257 total
includes taxes & fees
Oct 26 - Oct 27
Hokah Ohana House: Historic charm, Modern updates
A bedroom with a bed, a nightstand, a lamp, and a window with curtains.

15. Hidden Gem - 1BR/1Bath in Lax WI

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (18 reviews)
"Our stay was perfect! The host was easy to communicate with and even let us check in early. The place was so cute! The bed was super comfortable and everything looked good and felt clean. Very safe area and neighborhood. Such a bonus to have a restaurant attached to the property! We will for sure stay here again!"
United States
Heather
The price is CA $155
CA $236 total
includes taxes & fees
Oct 8 - Oct 9
Hidden Gem - 1BR/1Bath in Lax WI
A wooden deck with a bench, a white door, and hanging flower baskets.

16. The Bungaleau 1 Bedroom House In Cute Rivertown

The Bungaleau 1 Bedroom House In Cute Rivertown
Downtown Trempealeau
9.8 out of 10, Exceptional, (105 reviews)
"Perfect place for a relaxing visit "
United States
Lisa C.
The price is CA $178
CA $229 total
includes taxes & fees
Oct 5 - Oct 6
The Bungaleau 1 Bedroom House In Cute Rivertown
A cozy wooden gazebo with a cushioned bench, string lights, and a patterned rug.

17. 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, (68 reviews)
"I"
United States
Charlie
The price is CA $140
CA $243 total
includes taxes & fees
Oct 22 - Oct 23
Nostalgic Retro Cottage, Blocks Away from Mississippi River. Full Fenced in Yard
A beach with a clear sky and calm sea.

18. Studio Condo Near Lake Pepin - King Bed - Dewdrop

Studio Condo Near Lake Pepin - King Bed - Dewdrop
Pepin
8.4 out of 10, Very good, (12 reviews)
"This is our second time staying here. Very enjoyable! "
United States
Avery
The price is CA $118
CA $280 total
includes taxes & fees
Oct 5 - Oct 6
Studio Condo Near Lake Pepin - King Bed - Dewdrop
Fun decorations throughout the apartment. Ask us how you can rent the full floor!

19. Modern Downtown La Crosse Apartment

Modern Downtown La Crosse Apartment
Historic Downtown La Crosse
9.4 out of 10, Exceptional, (75 reviews)
"Nice, quiet property that's in a great location."
United States
Jacob P.
Modern Downtown La Crosse Apartment
A modern living room with a dark wooden bookshelf, a grey sofa, and a dining area with a wooden chair.

20. NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102

NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102
Wabasha
10.0 out of 10, Exceptional, (119 reviews)
"Great place"
United States
Mark
The price is CA $180
CA $223 total
includes taxes & fees
Oct 5 - Oct 6
NEW, NEW, NEW! Wabasha downtown studio113 Pembroke Ave Unit #102
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 County Hotel Reviews

The Charmant Hotel

The Charmant Hotel

10/10 Excellent
"Staff and hotel were amazing….other than the rooftop bar manager, but people can have a bad day. Otherwise absolutely outstanding from the valet to the front desk to the coffee shop and even the guest services manager."
Stefanie 1-night trip
Posted less than an hour ago
The Charmant Hotel

Find out more about Winona County

Everything you need to know about Winona County 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 County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winona County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona County. 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 County vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona County vacation rentals we have selected for you start as low as CA $223 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winona County rentals

At Expedia, we put the best Winona County 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 County 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 County 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 County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.