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Vacation rentals in Winona

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Top-rated vacation rentals in Winona

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Apartment in Winona
Cozy & Bright 2nd Floor Apt - 7 Blocks from WSU
Our newly-remodeled one-bedroom apartment is the perfect getaway for two guests. * Spacious bedroom with queen size bed, couch and workspace * Hardwood floors throughout * Full kitchen with oven, refrigerator, microwave + coffee/tea station * Walking distance to WSU and Cotter * Located on the 2nd floor with off-street parking * Your own washer dryer in the apartment * Easy self-check-in process We want you to love your time in Winona and are here to make your stay as pleasant as possible.
Feb. 11 – 18
$143 CAD per night
4.94 out of 5 average rating, 132 reviews
Guest favourite
Bungalow in Winona
*Prairie Island Bungalow with Water Access*
Welcome to Prairie Island Bungalow (PIB)! Located on Prairie Island in Winona, this home provides the perfect, quiet getaway for work or play, and is your gateway to outdoor adventure in the Winona area. River access is available on our private dock next door! With thoughtful amenities including a fully-stocked kitchen (with coffee and tea!), plush linens, Smart TVs, games and books, a fire pit, snowshoes, and kayak and canoe rentals; we invite you to simply show up and enjoy your stay at PIB!
Nov. 3 – 10
$261 CAD per night
4.99 out of 5 average rating, 147 reviews
Guest favourite
Home in Winona
Winona, MN- Cozy 3 bdrm bungalow with river view
Our home/cabin is up along the bluffs allowing eagle eye views of the Mississippi River. A perfect quiet place to take everything in. There are three bedrooms intended for large families or group get-aways. Everything is at your fingertips from beaches, to hikes in the bluffs. It is 3 miles south of Winona. While you can see the river, there is easy access to public landing if you choose to bring a boat to partake in the various islands and water sports.
Aug. 21 – 28
$197 CAD per night
4.91 out of 5 average rating, 200 reviews

Popular amenities for Winona vacation rentals

Stay near Winona's top sights

Prairie Island Campground3 locals recommend
Hy-Vee5 locals recommend
Bloedow's Bakery13 locals recommend
Bub's Brewing Co7 locals recommend
Acoustic Cafe15 locals recommend
Midtown Foods5 locals recommend

Other great vacation rentals in Winona

Guest favourite
Tiny homes in Winona
Potluck String Lodge (PSL)
Aug. 24 – 31
$246 CAD per night
4.99 out of 5 average rating, 118 reviews
Guest favourite
Apartment in Winona
Oma's Treehäus & Rooftop Deck
Apr. 16 – 23
$195 CAD per night
4.93 out of 5 average rating, 256 reviews
Guest favourite
Home in Winona
Spacious Retreat for 1-8 guests
Mar. 22 – 29
$313 CAD per night
4.95 out of 5 average rating, 110 reviews
Guest favourite
Home in Minnesota City
✨Vintage Lustron Home✨
Jun. 16 – 23
$172 CAD per night
4.98 out of 5 average rating, 269 reviews
Guest favourite
Farm stay in Dakota
The Bungalow at Heart and Soil Ridge
Dec. 31 – Jan. 7
$135 CAD per night
4.93 out of 5 average rating, 241 reviews
Guest favourite
Loft in Arcadia
Tamarack Point Homestead
Mar. 6 – 13
$133 CAD per night
4.98 out of 5 average rating, 116 reviews
Guest favourite
Apartment in Winona
Treetops Suite for Two @ 7th Street Retreat
Mar. 19 – 26
$123 CAD per night
4.94 out of 5 average rating, 67 reviews
Guest favourite
Home in Winona
Relaxing Stylish Home
Mar. 12 – 19
$185 CAD per night
5.0 out of 5 average rating, 19 reviews
Guest favourite
Cottage in Winona
Quiet Cottage in the Valley with Sauna
Aug. 18 – 25
$256 CAD per night
4.94 out of 5 average rating, 17 reviews
Guest favourite
Home in Winona
A Stone's Throw Bungalow
Oct. 23 – 30
$272 CAD per night
4.98 out of 5 average rating, 53 reviews
Guest favourite
Apartment in Winona
NOVA Treehouse
Sep. 18 – 25
$125 CAD per night
4.92 out of 5 average rating, 13 reviews
Guest favourite
Home in Winona
The Village House Inn
Mar. 20 – 27
$508 CAD per night
4.96 out of 5 average rating, 46 reviews

Quick stats about vacation rentals in Winona

Total rentals

70 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

6.1K reviews

Nightly prices starting at

$27 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Minnesota
  4. Winona County
  5. Winona