Winona Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winona vacation rentals

Big River Escape Parkside Bungalow

Big River Escape Parkside Bungalow
3.0 star property
Winona
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful time and would defiinitely stay again. "
United States
Julie
The price is CA $284
CA $317 total
includes taxes & fees
Apr 16 - Apr 17
Big River Escape Parkside Bungalow

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, (22 reviews)
"Had everything we needed and great communication for our weekend stay. "
United States
Tanya G.
The price is CA $207
CA $260 total
includes taxes & fees
Apr 20 - Apr 21
Charming 1-bedroom house in delightful Winona with WiFi, AC and PRIVATE PATIO

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, (26 reviews)
"Beautiful home we had a wonderful stay!!!"
United States
Thomas L.
The price is CA $358
CA $436 total
includes taxes & fees
Apr 16 - Apr 17
Charming 3-bedroom, 2 bathroom house with outdoor space in Winona

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, (139 reviews)
"Excellent home and area!"
United States
Tracy W.
The price is CA $359
CA $605 total
includes taxes & fees
Apr 19 - Apr 20
Charming Brick Farmhouse with a Touch of Elegance. -Winona

Ridgetop Retreat Tiny Home, Dakota MN

Ridgetop Retreat Tiny Home, Dakota MN
Dakota
9.8 out of 10, Exceptional, (8 reviews)
"Wonderful location, nice people"
United States
robert
The price is CA $149
CA $190 total
includes taxes & fees
Apr 20 - Apr 21
Ridgetop Retreat Tiny Home, Dakota MN

Great RIver Road Class A RV with campsite and full hookup on Mississippi backwaters

Great RIver Road Class A RV with campsite and full hookup on Mississippi backwaters
Buffalo City
10.0 out of 10, Exceptional, (1 review)
"Awesome as usual "
United States
Matthew B.
The price is CA $176
CA $214 total
includes taxes & fees
May 12 - May 13
Great RIver Road Class A RV with campsite and full hookup on Mississippi backwaters

Tamarack Point Homestead

Tamarack Point Homestead
Arcadia
10.0 out of 10, Exceptional, (35 reviews)
"What a wonderful place to stay. "
United States
Anonymous traveller
The price is CA $126
CA $162 total
includes taxes & fees
Apr 16 - Apr 17
Tamarack Point Homestead

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

French Island w/Hot Tub, Kayak, Lake View, EV
La Crosse
9.8 out of 10, Exceptional, (20 reviews)
"Enjoyed our stay in this peaceful, quiet neighborhood."
United States
Colleen C.
The price is CA $179
CA $431 total
includes taxes & fees
Apr 19 - Apr 20
French Island w/Hot Tub, Kayak, Lake View, EV

Studio Cottage at Lake Road Campground, near the beautiful Mississippi River.

Studio Cottage at Lake Road Campground, near the beautiful Mississippi River.
Trempealeau
8.0 out of 10, Very good, (5 reviews)
"We loved the cleanliness, location, quietness, and friendliness of the property manager. It was a great value for the money. We will stay again and we highly recommend!"
United States
Tracey H.
The price is CA $180
CA $230 total
includes taxes & fees
Apr 16 - Apr 17
Studio Cottage at Lake Road Campground, near the beautiful Mississippi River.

Treehouse Cabin in the Bluff Woodlands

Treehouse Cabin in the Bluff Woodlands
Elba
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful area enjoyed our stay immensely"
United Kingdom
I.M l.
The price is CA $129
CA $227 total
includes taxes & fees
Apr 19 - Apr 20
Treehouse Cabin in the Bluff Woodlands

Riverfront Twin Home

Riverfront Twin Home
La Crosse
10.0 out of 10, Exceptional, (47 reviews)
"It was the perfect weekend getaway!! "
United States
Theresa G.
The price is CA $186
CA $421 total
includes taxes & fees
Apr 19 - Apr 20
Riverfront Twin Home

Big River Escape Riverside Cabins

Big River Escape Riverside Cabins
3.0 star property
Cochrane
9.2 out of 10, Wonderful, (45 reviews)
"Place was clean and comfortable. "
United States
Tristan
The price is CA $128
CA $135 total
includes taxes & fees
Apr 21 - Apr 22
Big River Escape Riverside Cabins

Hokah Ohana House: Historic charm, Modern updates

Hokah Ohana House: Historic charm, Modern updates
Hokah
10.0 out of 10, Exceptional, (33 reviews)
"Perfect place for 4 of us to stay while visiting for a wedding. "
United States
Jeff W.
The price is CA $121
CA $255 total
includes taxes & fees
Apr 16 - Apr 17
Hokah Ohana House: Historic charm, Modern updates

Treehouse Cabin in the Bluff Woodlands North

Treehouse Cabin in the Bluff Woodlands North
Elba
9.6 out of 10, Exceptional, (9 reviews)
"Great relaxing place! "
United States
James H.
The price is CA $137
CA $237 total
includes taxes & fees
Apr 20 - Apr 21
Treehouse Cabin in the Bluff Woodlands North

Vintage Spring Getaway

Vintage Spring Getaway
Holy Trinity-Longfellow
9.4 out of 10, Exceptional, (34 reviews)
"Our stay was very nice. Tina was excellent in responding to a few of our needs. Lovey home and nicely decorated."
United States
Mary B.
The price is CA $167
CA $573 total
includes taxes & fees
Apr 20 - Apr 21
Vintage Spring Getaway

Hidden Gem - 1BR/1Bath in Lax WI

Hidden Gem - 1BR/1Bath in Lax WI
Holy Trinity-Longfellow
9.6 out of 10, Exceptional, (16 reviews)
"A lovely, spacious, clean apartment above a yummy restaurant in a quiet residential neighborhood. We stayed there when we were in town for a 6-hour race in Goose Island State Park, and it was perfect! "
United States
Amy
The price is CA $150
CA $228 total
includes taxes & fees
Apr 20 - Apr 21
Hidden Gem - 1BR/1Bath in Lax WI

Vintage Lustron Home Piece of History

Vintage Lustron Home Piece of History
Minnesota City
10.0 out of 10, Exceptional, (30 reviews)
"Every thing was great! We always enjoy staying here. The home was excellent and we had no issues."
United States
Lynda S.
The price is CA $186
CA $293 total
includes taxes & fees
Apr 17 - Apr 18
Vintage Lustron Home Piece of History

Jake's Place

Jake's Place
Powell-Poage-Hamilton
9.8 out of 10, Exceptional, (8 reviews)
"Great place, great location. Very clean & practical! "
United States
Cori C.
The price is CA $207
CA $448 total
includes taxes & fees
Apr 19 - Apr 20
Jake's Place

Great River Road Cabin on the Mississippi Backwaters Fox Cabin

Great River Road Cabin on the Mississippi Backwaters Fox Cabin
Buffalo City
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay and really enjoyed the screened in porch. Spent a lot of time sitting at the table in the screened in porch playing cards."
United States
Jenny D.
The price is CA $184
CA $223 total
includes taxes & fees
Apr 16 - Apr 17
Great River Road Cabin on the Mississippi Backwaters Fox Cabin

Farmhouse Apartment - River Road Historic Home

Farmhouse Apartment - River Road Historic Home
Fountain City
9.8 out of 10, Exceptional, (19 reviews)
"Great rental! Great location and very clean. Hidden gem!"
United States
Anthony y.
The price is CA $186
CA $321 total
includes taxes & fees
Apr 16 - Apr 17
Farmhouse Apartment - River Road Historic Home
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winona Hotel Reviews

Find out more about Winona

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Winona?

Yes, there are vacation rentals in Winona near Polish Cultural Institute & Museum Annex, or you can choose a secluded option if you want 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 vacation rentals that Winona has to offer?

River Front Property : This vacation home rental outside of Winona is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals are there in Winona?

Expedia has 13 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.