Winona vacation rentals

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Top-rated vacation rentals in Winona

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

Guest favorite

Loft in Winona

Penthouse Retreat-Near Downtown Winona!

Hi! This beautiful loft is conveniently located in the heart of Winona MN! Only a few blocks from the downtown and in close proximity to many other attractions Winona has to offer such as: Coffee, restaurants, a wine bar, Winona State University, Mississippi River, Lake Winona, hiking trails, Shakespeare Festival, Minnesota Marine Art Museum, and much more! Please allow us to make your next extended stay in beautiful Winona a memorable one! * MUST CLIMB STAIRS TO UNIT- LOCATED ON THE 3RD LEVEL

$96 per night
Guest favorite

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!

$102 per night
Guest favorite

Apartment in Winona

Entire 2nd Floor Apt with Extra Amenities

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.

$89 per night

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

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

$20 before taxes and fees

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Winona?

    Yes! Work meets play with ease at over 30 vacation rentals in Winona featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Winona?

    Four-legged friends are welcome in Winona. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do apartment rentals in Winona have air conditioning?

    Absolutely! We offer over 20 apartment rentals with air conditioning in Winona. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Winona have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Winona. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Winona?

    Winona has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Winona have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Winona. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Winona?

    Experience the best of Winona with our apartment rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Winona?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 10 homes with a bbq area, over 20 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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