Winona holiday rentals

We found 56 holiday rentals — enter your dates for availability
Discover a selection of 13 homes and other holiday rentals in Winona that are perfect for your trip. Holiday homes offer the best amenities for you and your friends, family or even pets, such as air conditioning and Wi-Fi. No matter what you're looking for, you'll be sure to find a property to rent for everyone's needs, including accessible or non-smoking choices.

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Take in the natural beauty of Winona

The area's museums and churches are just some of the reasons to come on holiday to Winona. Well known for its bird watching, wildlife and gardens, this scenic city won't disappoint. A holiday 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 discover things to do in the area? Venture out of your holiday home and experience everything that makes Winona a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Elmaro Vineyard (8 mi / 12.8 km)
  • The Craft Barn (17.5 mi / 28.2 km)
  • Cedar Valley Golf Course (8.9 mi / 14.3 km)
  • Trempealeau Mountain Golf Club (11.4 mi / 18.3 km)
  • Westfield Golf Club (0.6 mi / 0.9 km)
  • Garvin Heights Vineyard (2 mi / 3.3 km)

Exploring the natural landscape of Winona

Whether you're an adventurous traveller or just want to appreciate the scenery, Winona is a great place to get out in nature. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Lake Park (2.4 mi / 3.9 km)
  • Trempealeau Mountain (8.8 mi / 14.2 km)
  • Great River Trail (23.5 mi / 37.8 km)
  • Pettibone Park (25.7 mi / 41.4 km)
  • Riverside Park (26.3 mi / 42.4 km)
  • Root River (27.9 mi / 44.9 km)

Transport 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 centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Rochester, MN (RST-Rochester Intl.), which is 42.2 mi (67.8 km) away.

If you're travelling by train, the main station serving the city is Winona Station.

Frequently asked questions

What is the best area to stay in Winona when booking a holiday rental?
When considering the best area to stay in Winona, Minnesota for a holiday rental, the historic district is an excellent choice. This charming neighbourhood is known for its stunning architecture and quaint streets, making it a delight for those who appreciate history and culture. One of the top attractions nearby is the Winona County History Centre, which offers fascinating insights into the local heritage. Additionally, the beautiful Lake Winona provides a lovely spot for outdoor activities, such as kayaking or simply enjoying a leisurely stroll along the waterfront.Another appealing area to consider is the area near St. Mary's University, which not only offers a vibrant setting due to the student population but also hosts various cultural events throughout the year. Here, you'll find easy access to parks and recreational facilities, as well as the breathtaking views from Garvin Heights Park, which overlooks the Mississippi River.In total, Winona boasts a variety of properties available for holiday rentals, suiting different preferences and budgets.
Where are the best Winona ski resort rentals?
For skiing in Winona, Minnesota, the nearest ski area is located at Mount La Crosse, which is approximately a short drive away. For holiday rentals that provide convenient access to this ski resort, travellers should consider properties in the nearby towns of La Crosse and Holmen. In La Crosse, you can find various accommodation options, including modern apartments and cosy cabins, many of which come equipped with amenities such as full kitchens, fireplaces, and outdoor spaces for relaxation after a day on the slopes.The Holmen area also offers charming family homes and lodges that are superb for groups, featuring amenities like game rooms, hot tubs, and spacious living areas. These rentals typically provide a comfortable base for skiing while being close to local shops and dining options, allowing guests to easily enjoy the area's nightlife and culinary scene.Moreover, the scenic bluffs surrounding the region offer additional recreational activities, such as hiking and snowshoeing in the winter months. Properties in this area often highlight their proximity to nature trails, ensuring that guests can experience the natural beauty of the Driftless Region alongside their skiing adventures.
What is the most popular type of holiday rental accomodation in Winona?
In Winona, holiday houses are the most popular type of holiday rental, with about 52 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking to enjoy the scenic views of the Mississippi River. Additionally, there are around 32 apartments in the city, often located in convenient areas close to local attractions like the Great River Bluffs State Park. These apartments usually come with modern amenities, such as laundry facilities and comfortable living areas. For those seeking a more rustic experience, there are also several cabins and about 12 cottages available, providing a charming getaway in a natural setting.
Are there any family house rentals in Winona?
In Winona, Minnesota, there are numerous family-friendly house rentals available—specifically, around sixteen options to choose from. The city is known for its beautiful riverside setting and rich history, making it a wonderful destination for families.Visitors can find homes in neighbourhoods close to the Mississippi River, offering spacious living areas and amenities such as fully equipped kitchens for preparing meals together. Many properties also feature outdoor spaces suitable for children to play, along with comforts like Wi-Fi and air conditioning to enhance the stay.Additionally, families can enjoy local attractions such as the Great River Bluffs State Park, which provides excellent hiking trails and stunning views. The vibrant downtown area is also nearby, where you can explore shops, restaurants, and cultural sites.
Are there pet-friendly house rentals in Winona?
In Winona, there are several pet-friendly house rentals available, providing a welcoming environment for those travelling with their furry companions. Many of these homes come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces where pets can enjoy some fresh air.The city is surrounded by beautiful natural landscapes, with nearby parks like Lake Park and Garvin Heights Park offering ample opportunities for leisurely walks and outdoor activities with pets. These parks feature scenic trails, picnic areas, and stunning views of the Mississippi River, making them superb spots for both relaxation and recreation.Additionally, the local community is known for its pet-friendly atmosphere, with various cafes and shops that welcome pets, enhancing the overall experience for visitors.
Are there any remote work holiday rentals in Winona?
In Winona, Minnesota, there are numerous remote work holiday rentals available, with around 100 options to choose from. This charming city, situated on the banks of the Mississippi River, offers a range of accommodations that cater to remote workers. Many properties come equipped with essential amenities such as free Wi-Fi, desks, and comfortable chairs, ensuring a productive work environment.Travellers can find a variety of settings, from modern apartments in the heart of downtown to cozy homes in quieter neighbourhoods. Having access to local cafes and parks can provide an excellent balance between work and relaxation. Additionally, the scenic views of the surrounding bluffs and riverfront make it an inspiring place to stay while managing remote work commitments. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Winona?
In Winona, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature onsite parking, making it convenient for those travelling with their own vehicles. Coffee and tea makers are commonly available, providing a warm beverage option for guests at their leisure. Air conditioning is a sought-after amenity, particularly during the warmer months, ensuring a comfortable indoor environment. Additionally, many holiday rentals offer outdoor spaces such as decks or patios, great for relaxing and enjoying the scenic views of the surrounding area.
When is the best time to visit Winona for a holiday rental?
The best time to visit Winona for a holiday rental is during the peak season from July to September, when the city comes alive with vibrant activities and beautiful weather. This summer period invites outdoor enthusiasts to enjoy hiking, biking, and exploring the picturesque bluffs along the Mississippi River, with temperatures typically ranging from 20 to 30 degrees Celsius.July stands out as the most popular month, offering a bustling atmosphere as locals and visitors alike partake in festivals and events, such as the Great River Shakespeare Festival. This lively celebration allows you to immerse yourself in culture while enjoying the warm evenings under the stars.For those seeking a more budget-friendly experience, consider visiting in December. While this is the low season, it offers a unique charm with winter activities like cross-country skiing and the opportunity to experience Winona's festive holiday decorations. The quieter streets make for a peaceful retreat, allowing you to savour the beauty of the season without the crowds.
What are the top attractions in Winona?
In Winona, visitors can enjoy a variety of attractions that showcase the area's natural beauty and rich history. The Mississippi Riverfront offers a picturesque setting where travellers can stroll along the scenic pathways or take part in water activities. The nearby Garvin Heights Park provides stunning panoramic views of the river and the surrounding bluffs, making it a popular spot for hiking and picnicking.For those interested in culture, the Great River Shakespeare Festival is a highlight, attracting theatre enthusiasts from far and wide. The Winona County Historical Society Museum is also worth a visit, as it features exhibits that delve into the region's history and heritage.Nature lovers can explore the breathtaking trails at the Root River State Trail, which is ideal for biking and walking, while the nearby Weaver Bottoms is a great location for birdwatching, especially during migration seasons.
Are all fees included in the Winona holiday homes prices shown on Stayz?
Stayz 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.
Are there any Winona holiday homes with parking?
Stayz offers a wide selection of holiday homes in Winona with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Winona holiday homes?
You can find great discounts on holiday homes in Winona on Stayz, 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.
Can I change or cancel my Winona holiday home booking on Stayz?
To find Winona holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Winona?
A long-stay holiday home in Winona is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Winona holiday home?
Book your Winona holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Winona?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Winona to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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