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Winona vacation rentals

We found 65 vacation rentals — enter your dates for availability

Discover a selection of 15 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.

Vacation rentals with weekly discounts - Winona

Showing deals for:Nov 14 - Nov 21
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Find out more about Winona

Find out more about Winona

Why visit Winona

  1. Stunning natural landscapes: Enjoy the picturesque foothills and scenic riverfront that showcase Winona's natural beauty.
  2. Rich cultural heritage: Explore historic buildings and vibrant neighborhoods that reflect the town's unique history.
  3. Outdoor activities: Engage in a variety of recreational activities, perfect for family fun or romantic outings.
  4. Educational experiences: Discover modern colleges and universities that contribute to the town's lively atmosphere.
  5. Charming accommodations: Choose from cozy cabins, spacious homes, or modern apartments for a comfortable stay.

Popular types of accommodation in Winona

Discover the charm of Winona with our selection of vacation rentals. Whether you're seeking a cozy cabin, a spacious private vacation home, or a modern apartment, we have options to suit every traveller. Explore the best Winona vacation rentals, including new apartments and inviting homes, all designed to provide comfort and convenience during your stay. Your perfect getaway in Winona awaits!

  • Houses: The top choice for visitors in Winona, these homes provide a comfortable and spacious setting for families or groups.
  • Cabins: A close second, cabins offer a rustic charm, perfect for those seeking a serene getaway amidst nature.
  • Apartments: Ideal for solo travellers or couples, apartments provide a convenient and cozy option for your stay.
  • Condos: These modern accommodations blend comfort and luxury, catering to those who desire a stylish experience.
  • Cottages: Quaint and inviting, cottages in Winona are perfect for a charming retreat.**

Top attractions in Winona

Winona, Minnesota, is a charming destination perfect for outdoor and romantic getaways, offering stunning scenery and a range of activities. Visitors can explore modern colleges and universities, urban parks, and historic buildings that reflect the town's rich culture. Whether you're seeking family-friendly experiences or simply wish to soak in the natural beauty, Winona has something for everyone to enjoy during their vacation.

  1. Winona State University: This vibrant university offers a blend of academic excellence and city energy. Wander through its modern campus, engaging with students and enjoying the lively atmosphere that defines this educational hub.
  2. Minnesota Marine Art Museum: Immerse yourself in the rich cultural tapestry at this museum, featuring stunning maritime art and exhibits that celebrate the region's nautical heritage, making it a must-visit for art enthusiasts.
  3. Sugar Loaf: A striking natural landmark, Sugar Loaf offers breathtaking views and picturesque hiking trails, perfect for outdoor enthusiasts looking to experience Winona's scenic beauty.

Things to do recommended for couples

For a romantic getaway in Winona, visit Garvin Heights Vineyard for delightful wine and stunning views. Don't miss Elmaro Vineyard, just 12.9km away, where you can enjoy a cozy atmosphere and live entertainment, perfect for couples looking to relax and connect.

Things to do recommended for families

Families can explore the wellness vibes at Lake Lodge Recreation Center, enjoy the serene landscapes of Goodview Park, and unwind at Bluffside Park, all perfect spots for relaxation and outdoor fun in Winona.

Things to do recommended for groups

Experience group fun at Cedar Valley Golf Course for a round of golf, hike the Sugar Loaf Trailhead for stunning views, or explore the Prairie Moon Sculpture Garden, located 20.9km from Winona, for a unique artistic adventure.

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

If you're planning a trip with friends, family, or pets, or seeking extended stays, it's important to prioritize your needs during your search. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Winona with a group: Think about how many bedrooms you require, as well as additional features like a complete kitchen or outdoor space for group get-togethers. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Winona with young kids: Traveling with young children can present its challenges. It’s important to prioritise 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 family-friendly attractions.
  • Taking your pets with you to Winona: For many families, a trip wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and 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 rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Winona

Winona, Minnesota, offers a delightful blend of outdoor adventures and romantic scenery, perfect for your vacation. Explore the picturesque foothills and historical neighborhoods that surround this charming city. Popular spots like the stunning riverfront and unique local attractions create an inviting atmosphere for all travellers. Don't miss the opportunity to experience the beauty of the region while enjoying recreational activities in and near Winona, ensuring a memorable getaway.

  • Fountain City: Located approximately 9.7km from Winona, Fountain City is a charming city embraced by the natural beauty of the Mississippi River. This destination is perfect for outdoor enthusiasts and romantics alike, offering scenic views and a tranquil atmosphere. Visitors can enjoy a variety of recreational activities, including hiking and biking along the trails, or exploring the nearby national state park. With picturesque lakes and rivers, Fountain City is an ideal spot for picnicking and unwinding in nature’s embrace.
  • Goodview: Nestled within the greater Winona area, Goodview is a delightful village that invites adventure seekers and nature lovers. Known for its beautiful lakes and vibrant community, Goodview offers a range of outdoor activities, from kayaking to hiking. The village is also home to an entertainment arena and an art museum, providing cultural and recreational experiences for visitors. The nearby national park adds to the charm, making it an excellent location for both relaxation and exploration.
  • Historic Downtown Winona: This vibrant neighbourhood is the heart of Winona, rich in history and culture. Visitors flock to Historic Downtown Winona for its scenic river views and access to hiking trails. The area features a modern college university, which adds a youthful energy to the historic streets. With skiing opportunities nearby and a variety of educational attractions, this neighbourhood is perfect for those looking to combine adventure with a touch of history. Explore the historic buildings and enjoy the lively atmosphere that defines Winona.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January16.5°F (-8.6°C)No Rain (Dry)Mostly CloudySlightly LowSlightly Low
February18.7°F (-7.4°C)No Rain (Dry)Mostly CloudyAverageAverage
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 simple

Looking to save on your next adventure? Consider being flexible with your travel dates, as prices can fluctuate. Also, opting for a longer stay can lead to significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your next adventures, pick up right where you left off, or manage your travel arrangements. You can easily access the properties you've saved and booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/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:

  • 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)
  • Houston Nature Center (20.7 mi / 33.4 km)
  • Shenanigans Entertainment Center & Sports Bar (24.5 mi / 39.5 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:

  • Sugar Loaf (2.7 mi / 4.4 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)
  • Root River (27.9 mi / 44.9 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 when booking a vacation rental?
If you're thinking about a Winona getaway, Goodview is one of the most desirable places to stay. Whether you prefer a chalet, cottage or another property style, you'll always have the entire place to yourself.
What is the most popular type of vacation rental accommodation in Winona?
Based on our data, houses are the most popular type of property in Winona. But naturally, everyone's idea of the perfect stay isn't the same. Vrbo has vacation homes of all shapes, sizes and budgets, and we'll help you discover your ideal fit.
How much does it cost to rent a vacation rental in Winona?
Property type, length of stay and season are some of the things that can influence the price of a vacation home. Simply add your travel dates to find your ideal escape. From cozy cabins to plush villas, all Vrbo vacation rentals provide incredible value.
How much does it cost to rent a beach house in Winona?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Put in your Winona travel dates to see all your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use our filters to pick the amenities and features you need.
What are popular rental amenities in Winona?
A firepit, nearby museums and a garden top the list of most popular rental amenities in Winona. Whether you're planning to travel solo, with your other half or a group of dear friends, Vrbo will help you find a vacation home that matches your tastes with a load of extras you'll love.
What are the top attractions for families in Winona?
Keep your kids occupied at these awesome family-friendly attractions in Winona:

  • Winona County Historical Society
  • Minnesota Marine Art Museum
  • Lake Lodge Recreation Center

How old do you have to be to rent a vacation rental in Winona?
We advise checking with the Winona vacation rental you'd like on Vrbo as age restrictions differ. However, it's normally 16, 18 or 21.
How long can I rent a vacation rental in Winona for?
It's down to the Winona property. To look over a list of options offering extended stays, just enter your dates and guest number into Vrbo's search page. You can enjoy having the whole place to yourself, as well as comforts such as a full kitchen, air conditioning and outdoor spaces where the kids can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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