Winona holiday rentals

We found 45 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Winona to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

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The natural setting of Winona is ready to explore

Learn about the unique charm of Winona with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Winona

Do you want to discover attractions to see in the area? Venture out of your cosy holiday rental and check out everything that Winona has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Big Spring (18.6 mi / 29.9 km)
  • Echo Bluff State Park (21.2 mi / 34.2 km)
  • Rocky Falls (8.4 mi / 13.6 km)
  • Roy L. Beck Municipal Golf Course (10.2 mi / 16.4 km)

Exploring the natural landscape of Winona

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Winona is a great place to spend some time outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Big Spring (18.6 mi / 29.9 km)
  • Current River State Park (22.8 mi / 36.7 km)
  • Rocky Falls (8.4 mi / 13.6 km)
  • Cave Spring Park (16 mi / 25.8 km)
  • Round Spring Cave (19.4 mi / 31.3 km)
  • Mahan Roadside Park (7 mi / 11.2 km)

Frequently asked questions

What is the best area to stay in Winona when booking a holiday rental?
When considering a holiday rental in Winona, Missouri, a popular area to stay is near the charming downtown district. This area offers a delightful blend of local shops, eateries, and a friendly atmosphere that captures the essence of small-town America. The proximity to the scenic Current River makes it an ideal spot for those who enjoy outdoor activities such as fishing, kayaking, or simply taking in the beautiful surroundings.Another appealing neighbourhood is close to the Mark Twain National Forest, which provides ample opportunities for hiking and exploring nature. This area is superb for families and nature enthusiasts who wish to immerse themselves in the great outdoors.In terms of accommodation, the downtown area typically features a modest selection of properties ranging from quaint cabins to comfortable homes, providing a variety of choices for visitors. Additionally, you will find the nearby forest area offers a few more secluded options, superb for those seeking tranquility.
What is the most popular type of holiday rental accomodation in Winona?
In Winona, cabins and holiday houses are the most popular types of holiday rentals, with several options available throughout the area. These properties typically provide a rustic charm, featuring ample space for relaxation and recreation. Most cabins come equipped with essential amenities such as fully fitted kitchens, comfortable living areas, and outdoor spaces ideal for enjoying the natural surroundings. Holiday houses also offer similar comforts, making them suitable for families or groups looking for a home-away-from-home experience.
Are there any family house rentals in Winona?
In Winona, Missouri, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The town offers a variety of properties, many of which are situated near scenic areas superb for outdoor activities. Visitors can expect homes with spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy playing.Additionally, the surrounding natural beauty provides opportunities for hiking, fishing, and exploring local wildlife, ensuring that families have ample options for adventure.
Are there pet-friendly house rentals in Winona?
In Winona, Missouri, there are several pet-friendly house rentals available, providing a welcoming environment for travellers with pets. Many of these holiday homes come equipped with essential amenities such as fully stocked kitchens, spacious living areas, and outdoor spaces, allowing for a comfortable stay.The rentals are often located near the scenic Ozark National Scenic Riverways, where visitors can enjoy activities like hiking, fishing, and canoeing with their pets. The tranquil surroundings and rich natural beauty of the area make it an excellent choice for those looking to explore the outdoors while having their furry companions by their side.
Are there any remote work holiday rentals in Winona?
In Winona, Missouri, there are several holiday rentals available that cater to remote work needs. Many of these properties come equipped with essential amenities such as reliable Wi-Fi and dedicated workspace areas, including desks and comfortable chairs, ensuring a productive environment for those working remotely.The scenic beauty of Winona, located near the Ozark National Scenic Riverways, offers an inspiring backdrop for remote work, with opportunities for outdoor activities to enjoy during breaks. 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 kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing a lovely outdoor space to relax and enjoy the surrounding scenery. For those who appreciate their morning brew, rentals often come equipped with coffee and tea makers. Additionally, travellers can find options that permit pets, making it easier for families to bring their furry companions along. A few properties may also include blenders, great for whipping up smoothies or other refreshments.
When is the best time to visit Winona for a holiday rental?
The peak travel season in Winona runs from May to July, when the region comes alive with vibrant outdoor activities. July, in particular, is the most popular month to visit, offering warm temperatures that typically range from 20 to 30 degrees Celsius. This is an ideal time for those seeking adventure, as visitors can enjoy hiking, kayaking, and exploring the stunning natural beauty of the Ozark National Scenic Riverways.During this lively season, the area attracts both families and solo travellers eager to embrace the great outdoors. The longer daylight hours provide ample opportunity for sightseeing and enjoying local events, making it a superb time for adventure seekers and nature enthusiasts alike.For those looking for a more budget-friendly option, consider planning your visit in October. This month may be quieter, but it offers a chance to experience the breathtaking autumn foliage, with the vibrant hues of leaves creating a picturesque backdrop for leisurely walks and scenic drives.Ultimately, the best time to book a holiday rental in Winona depends on whether you prefer the energetic buzz of summer adventures or the tranquil beauty of fall.
What are the top attractions in Winona?
In Winona, Missouri, visitors can enjoy a range of attractions that highlight the area's natural beauty and outdoor activities. The nearby Current River is a popular spot for canoeing, kayaking, and fishing, offering a serene experience surrounded by lush landscapes. The Ozark National Scenic Riverways, which includes sections of the Current River, provides hiking trails and opportunities for wildlife viewing, making it great for nature enthusiasts.The town itself features charming local shops and eateries, where visitors can experience the friendly atmosphere of small-town Missouri. Additionally, the surrounding area is known for its picturesque bluffs and scenic views, with many opportunities for photography and exploration.
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.