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Winona vacation rentals

We found 58 vacation rentals — enter your dates for availability

Discover a selection of 13 homes and other vacation rentals in Winona that are perfect for your trip. Vacation homes provide the best amenities for your family, friends, or furry companion, such as WiFi and a pool. At the end of the day, you'll find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

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Find out more about Winona

Why visit Winona

  • Scenic Outdoor Adventures: Enjoy beautiful landscapes around Lake Onalaska, perfect for hiking and relaxation.
  • Cultural Experiences: Explore engaging art museums and the vibrant atmosphere of the Winona State University campus.
  • Historical Neighborhoods: Discover charming neighborhoods that offer a glimpse into Winona's rich history.
  • Romantic Getaways: Ideal for couples, with picturesque spots and cozy accommodations like cabins and vacation homes.
  • Family-Friendly Activities: Winona caters to all ages, providing fun and engaging options for families.

Popular types of accommodation in Winona

If you're looking for the perfect getaway in Winona, you're in luck. Our most popular vacation rental options include houses, charming cabins, and comfortable apartments. Whether you need a cozy spot near campus housing or a pet-friendly rental, we offer quality housing to suit your needs. Discover the ideal place to unwind while enjoying all that Winona has to offer.

  • Houses: The top choice for visitors to Winona, offering spacious and comfortable accommodations ideal for families or groups.
  • Cabins: A popular option for those seeking a rustic experience, nestled in nature for a tranquil getaway.
  • Apartments: Perfect for solo travelers or couples, these rentals provide the convenience of home in the heart of the city.
  • Condos: A modern alternative, combining comfort with amenities, great for short or long stays.
  • Cottages: These quaint and cozy spaces are perfect for a romantic escape or a peaceful retreat.**

Top attractions in Winona

Winona, Minnesota, is perfect for outdoor enthusiasts and those seeking a romantic getaway, offering a blend of scenic beauty and cultural experiences. Visitors can explore modern colleges, lush urban parks, and engaging art museums. Whether you're looking for family-friendly activities or a taste of local culture, Winona has something for everyone, making it an ideal destination for your vacation.

  • Winona State University: This vibrant campus offers a modern atmosphere with stunning architecture and beautiful green spaces, perfect for a leisurely stroll. Engage with students and faculty, and immerse yourself in the educational spirit of the community.
  • Minnesota Marine Art Museum: Featuring an impressive collection of marine-themed artwork, this museum provides a cultural experience with its stunning exhibits and serene ambiance, ideal for art lovers and history enthusiasts alike.
  • Winona County Courthouse: A historic landmark showcasing impressive architecture and rich local history. Explore its grand interiors and learn about the heritage of Winona through informative displays.

Things to do recommended for couples

For a romantic getaway in Winona, visit Garvin Heights Vineyard for stunning views and delightful wines. Just 8 miles away, Elmaro Vineyard offers a charming atmosphere perfect for couples looking to unwind and enjoy each other's company amidst beautiful scenery.

Things to do recommended for families

Families visiting Winona can have a fantastic time at Lake Lodge Recreation Center, where wellness meets fun, or enjoy the scenic Bluffside Park for relaxation. Cotter Fields also offers a great recreational space for kids to play and explore, making it a perfect family-friendly destination.

Things to do recommended for groups

Experience a day at Cedar Valley Golf Course for some friendly competition or hike the scenic Sugar Loaf Trailhead for stunning views. Don't miss the Prairie Moon Sculpture Garden, a unique store just 13 miles from Winona, perfect for group exploration and memorable photos.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Winona

When you're planning a trip—whether it's with a group, family, or pets, or if you're interested in longer stays—be sure to refine your search based on what matters most to you. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Winona with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor space for group gatherings. The good news is that you can easily filter for all of these options and so much more on Vrbo.
  • Traveling to Winona with young kids: Traveling with young children can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are enjoyable for families.
  • Taking your pets with you to Winona: For many families, a getaway isn't truly fulfilling without their furry companion by their side. If this resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Winona: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Winona

Winona, Minnesota, offers a charming blend of outdoor adventure and romantic scenery. Explore the picturesque lake Onalaska and enjoy island city living just beyond the city limits. The vibrant atmosphere around the WSU campus adds a youthful energy, while the nearby historical neighborhoods provide a glimpse into the past. Whether you're seeking recreation or relaxation, Winona’s unique vibes promise a memorable vacation experience.

  • Fountain City: Located a short 6 miles from Winona, Fountain City is a charming destination known for its stunning outdoor scenery and romantic ambiance. Visitors flock to this city for its recreational areas and hiking trails that wind through picturesque landscapes. Enjoy the serene beauty of the nearby river and lake, and take advantage of the access to national state parks. Whether you’re looking for a peaceful retreat or an adventurous day outdoors, Fountain City offers a delightful escape.
  • Historic Downtown Winona: Nestled in the heart of Winona, the Historic Downtown area is a vibrant neighborhood rich in history and adventure. Here, travelers can explore educational venues, enjoy trail access, and even try their hand at skiing in the winter months. The scenic riverside and the presence of a modern college university add to the charm, while numerous historic sites provide a glimpse into the past. Strolling through the streets, you'll find unique shops and eateries that reflect the area's cultural heritage.
  • Goodview: Just a stone's throw from Winona, the village of Goodview is a hidden gem for outdoor enthusiasts and adventurers. This quaint village boasts recreational areas and an arena entertainment facility, perfect for family fun. Explore the local lake or visit historic houses that tell the story of the region. With its scenic views and friendly atmosphere, Goodview is a wonderful spot to relax and enjoy the natural beauty of the area.

Best time to go to Winona

If you're planning a trip to Winona, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April, July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January16.5°F (-8.6°C)No Rain (Dry)Mostly CloudySlightly LowAverage
February18.7°F (-7.4°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
March33.6°F (0.9°C)Light RainMostly CloudyAverageSlightly Low
April44.8°F (7.1°C)Light RainMostly CloudySlightly HighSlightly Low
May57.6°F (14.2°C)Light RainMostly SunnyAverageAverage
June67.6°F (19.8°C)Light RainMostly SunnyAverageAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August69.8°F (21.0°C)Light RainMostly SunnyAverageSlightly High
September62.8°F (17.1°C)Light RainMostly SunnySlightly HighAverage
October48.9°F (9.4°C)Light RainMostly SunnyAverageAverage
November35.8°F (2.1°C)No Rain (Dry)Mostly SunnySlightly LowAverage
December23.5°F (-4.7°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider keeping your travel dates flexible, as prices can fluctuate significantly. Also, extending your stay can often lead to substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's Trip Board offers a user-friendly area where you can easily create new trips, resume planning from where you last stopped, or organize your travel arrangements. You'll discover your saved or booked properties neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Take in the natural beauty of Winona

The area's museums and churches are just a few of the reasons to vacation in Winona. Well known for its bird watching, wildlife and gardens, this scenic city won't disappoint. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Winona

Are you hoping to find attractions to visit in the city? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Winona a fun place to get away. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Shenanigans Entertainment Center & Sports Bar (24.5 mi / 39.5 km)
  • Elmaro Vineyard (8 mi / 12.8 km)
  • Cedar Valley Golf Course (8.9 mi / 14.3 km)
  • Trempealeau Moutain Golf Club (11.4 mi / 18.3 km)
  • The Craft Barn (17.5 mi / 28.2 km)
  • Westfield Golf Club (0.6 mi / 0.9 km)

Exploring the natural landscape of Winona

Whether you're looking for exciting outdoor activities or just want to take in the scenery, you'll be sure to find the perfect setting for your vacation in Winona. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Lake Lodge Recreation Center (1.5 mi / 2.4 km)
  • Lake Park (2.4 mi / 3.9 km)
  • Trempealeau Mountain (8.8 mi / 14.2 km)
  • Brady's Bluff (9.4 mi / 15.1 km)
  • Great River Trail (23.5 mi / 37.8 km)
  • Riverside Park (26.3 mi / 42.4 km)

Transportation options to and around Winona

The nearest airport is in La Crosse, WI (LSE-La Crosse Municipal), located 23.6 mi (37.9 km) from the city center. If you're unable to find a flight that fits your schedule, you can also fly into Rochester, MN (RST-Rochester Intl.), which is 42.2 mi (67.8 km) away.

If you prefer train travel, the main station serving the city is Winona Station.

Frequently asked questions

What is the best area to stay in Winona, Minnesota, United States of America when booking a vacation rental?
When looking for the best area to stay in Winona, Minnesota, consider the charming downtown district. This vibrant neighborhood offers a delightful mix of historic architecture and modern amenities, making it a superb spot for vacation rentals. You'll find a variety of properties, from cozy apartments to quaint homes, providing ample options for travelers.

Staying downtown puts you within walking distance of top attractions such as the Winona County Historical Society, where you can delve into the rich local history, and the beautiful Lake Park, superb for leisurely strolls or picnics. Additionally, the area is known for its vibrant dining options and unique shops, enhancing your overall experience in this picturesque riverside town.

Another great option is the area near the Bluffs, which offers stunning views and access to outdoor activities like hiking and biking. This neighborhood provides a more tranquil setting while still being close to downtown attractions.
How much does it cost to rent a vacation home in Winona?
Prices for vacation rentals in Winona vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Winona to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Winona vacation house rentals?
You can find great discounts on house rentals in Winona on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Winona ski resort rentals?
For skiing near Winona, Minnesota, travelers should consider the options available at nearby ski areas like Mount La Crosse, which is about a 30-minute drive away. In the vicinity of this ski resort, visitors can find various rental options in the city of La Crosse, where there are numerous hotels and vacation rentals that cater to winter sports enthusiasts. Many properties in this area offer amenities such as ski storage, complimentary breakfast, and heated indoor pools, superb for relaxing after a day on the slopes.

In addition to La Crosse, the charming town of Onalaska offers further rental choices, often featuring comfortable lodgings equipped with kitchens and cozy living spaces. Many of these properties provide easy access to local dining and shopping options, enhancing the convenience for travelers.

For outdoor lovers, the surrounding bluffs of the Mississippi River Valley present opportunities for hiking and snowshoeing during the winter months. Rentals in the area often boast picturesque views of the river and the stunning landscape, making them ideal for those looking to enjoy both skiing and the natural beauty of the region.
What is the most popular type of vacation rental accomodation in Winona?
In Winona, vacation houses are the most popular type of rental, with about 13 available throughout the area. These houses typically feature multiple bedrooms, fully equipped kitchens, and spacious living areas, making them ideal for families or groups seeking a comfortable stay. Additionally, there are several apartments, cottages, and cabins scattered around the scenic neighborhoods, which provide a variety of options for different preferences. Many of these rentals include outdoor spaces, allowing guests to relax and enjoy the beautiful surroundings of this charming town.
Are there any family house rentals in Winona?
In Winona, Minnesota, there are 16 family-friendly house rentals available, offering a variety of options for those traveling with children. Visitors can explore the charming neighborhoods of the city, where many properties feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces great for family gatherings or playtime.

Properties often come with amenities such as Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay for larger groups. The proximity to local attractions, including the beautiful Mississippi River and several parks, provides ample opportunities for outdoor activities and exploration.
Can I find long-stay vacation rentals in Winona?
A long-stay vacation rental in Winona is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Winona?
In Winona, there are several pet-friendly house rentals available, offering a great mix of comfort and convenience for travelers with pets. Many of these vacation homes are situated near picturesque locations like the Mississippi River, providing easy access to walking trails and scenic views.

Travelers can expect amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces where pets can enjoy the fresh air. Some properties may even feature fenced yards, making it easier for pets to roam safely.

The area also has local parks, such as Lake Park, which is a lovely spot for leisurely strolls and picnics, ensuring that both guests and their furry companions can enjoy the natural beauty of Winona. See all pet-friendly rentals in Winona.
Are there any remote work vacation rentals in Winona?
In Winona, Minnesota, there are numerous vacation rentals suitable for remote work, with around 25 options available. Travelers can expect properties equipped with essential amenities such as reliable Wi-Fi, dedicated workspaces, and comfortable living areas, making them conducive for productivity. Many rentals feature modern kitchens, allowing for convenient meal preparation, and some offer outdoor spaces where guests can unwind after a day of work.

The town itself provides a charming atmosphere, with access to local coffee shops and parks, great for breaks or casual meetings. The scenic beauty of the Mississippi River adds to the appeal, offering opportunities for outdoor activities during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Winona vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Winona with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Winona?
In Winona, popular vacation rental amenities include fully equipped kitchens, which allow travelers to prepare their own meals during their stay. Many rentals also offer onsite parking, making it convenient for those traveling by car. Coffee and tea makers are commonly found in these properties, ensuring guests can enjoy their morning beverages with ease. Air conditioning is another sought-after amenity, providing comfort during warmer months. Additionally, many rentals feature decks or patios, offering outdoor space to relax and enjoy the beautiful surroundings of this charming Minnesota town.
When is the best time to visit Winona for a vacation rental?
July is the most popular time to visit Winona, as it falls within the peak season that runs from July to September. This vibrant summer month attracts outdoor enthusiasts and families alike, drawn to the city's picturesque riverfront and abundant recreational activities. Visitors can enjoy hiking, biking, and exploring the stunning natural landscapes that surround the area, including the scenic bluffs of the Mississippi River.

During July, temperatures typically range from the mid-60s to the low 80s Fahrenheit, providing a warm and comfortable climate for outdoor adventures. The long days are great for sightseeing, whether you're strolling along the riverwalk, visiting local festivals, or taking in the area's rich history through its charming architecture.

For those looking for more budget-friendly options, consider planning your visit in December. While this month is outside the high tourist season, it offers a unique chance to experience Winona's winter charm, from holiday festivities to cozy indoor activities. The peaceful atmosphere allows for intimate exploration of the city's cultural offerings without the hustle and bustle of peak season.

Ultimately, the best time to book a vacation rental in Winona hinges on your preference for lively summer activities or a quieter, more serene winter experience.
How early should I book a Winona vacation rental?
Book your Winona vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Winona, Minnesota, United States of America?
In Winona, visitors can explore a variety of attractions that highlight the area's natural beauty and cultural heritage. The Mississippi Riverfront is a focal point, offering scenic views and recreational opportunities such as boating and fishing. Along the river, Levee Park features walking trails, picnic areas, and hosts community events throughout the year.

The historic downtown area, with its charming architecture, is home to numerous shops, cafes, and art galleries. The Winona County Historical Society Museum offers insight into the region's past, while the nearby Polish Cultural Institute showcases the town's rich Polish heritage.

For outdoor enthusiasts, Garvin Heights Park provides hiking trails and panoramic views of Winona and the river valley, making it a popular spot for both locals and tourists. Additionally, the nearby Root River State Trail is ideal for biking and walking, connecting Winona to other scenic areas in the region.
Can I change or cancel my Winona home rental booking on Vrbo?
To find Winona vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Winona vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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