Winona holiday rentals

We found 5 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Winona that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll have the amenities that you expect and more, including air conditioning and Wi-Fi. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Travel to friendly Winona

Learn about the unique charm of Winona with a stay in a holiday home rental. This welcoming city is known for its coffee shops, baseball games and golfing. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in Winona

Are you hoping to discover attractions to see in the city? Venture out of your holiday home and experience everything that Winona has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Grenada Country Club (19.4 mi / 31.3 km)
  • Winona Country Club (2.5 mi / 4.1 km)
  • Dogwoods Golf Course (22.2 mi / 35.7 km)
  • Perry Creek Golf & Racquet Club (19.4 mi / 31.2 km)
  • Greenwood Country Club Golf Course (24.6 mi / 39.6 km)

Exploring the natural features in Winona

Whether you're an active traveller or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Winona. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Hugh White State Park (23 mi / 37.1 km)
  • Grenada Lake (24.4 mi / 39.3 km)
  • Lakeview Public Use Area (21.4 mi / 34.5 km)
  • Magnolia Memorial Roadside Park (20.6 mi / 33.1 km)
  • Bledsoe Park (20.6 mi / 33.2 km)
  • Old Fort Public Use Area (21.6 mi / 34.8 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, Mississippi, the downtown area is an excellent choice. This vibrant neighbourhood boasts a charming atmosphere with a mix of local shops and eateries that provide a taste of the region's culture. A popular attraction nearby is the Winona-Montgomery County Airport, which serves as a convenient gateway for visitors. Additionally, the scenic Lake Monocnoc is just a short drive away, offering opportunities for outdoor activities like fishing and picnicking.Another appealing area is the vicinity around the historic district, where you can explore beautiful architecture and learn about the town's rich history. This area features a selection of properties that often reflect the character of Winona, making it a delightful place to stay.
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 accommodations often feature rustic charm and are situated in serene locations, providing a peaceful retreat for travellers. Most cabins come equipped with essential amenities such as kitchens, comfortable living spaces, and outdoor areas for enjoying the natural surroundings. Holiday houses, on the other hand, tend to offer more space, making them suitable for families or larger groups. These properties typically include multiple bedrooms and inviting outdoor spaces, great for gatherings.
Are there any remote work holiday rentals in Winona?
In Winona, Mississippi, there are several holiday rentals suitable for remote work. Many of these properties are equipped with essential amenities such as free Wi-Fi and dedicated workspaces, including desk and chair setups, ensuring a comfortable environment for productivity. The charming town offers a peaceful atmosphere, making it an ideal spot for those looking to blend work and leisure.Exploring Winona, you can discover its local culture, including quaint shops and eateries, which provide a taste of Southern hospitality. The surrounding natural beauty adds to the appeal, with opportunities for outdoor activities in the nearby landscapes. 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 essential features that enhance comfort and convenience for travellers. Most holiday rentals come equipped with kitchens, allowing guests to prepare their own meals. Additionally, many properties offer air conditioning to ensure a pleasant indoor climate, especially during warmer months. A desk and desk chair are also commonly found, making it easier for those who need to work or study during their stay. For a touch of hospitality, many rentals provide a coffee and tea maker, superb for enjoying a warm beverage in the morning or after a day of exploring.
When is the best time to visit Winona for a holiday rental?
June is the most popular month to visit Winona, Mississippi, as it falls within the vibrant peak season that spans from May to July. This time of year is ideal for those seeking outdoor adventures and cultural experiences, with plenty of festivals and events taking place in the area. Visitors can enjoy the warm Southern climate, typically ranging from the mid-teens to low 30s Celsius, making it superb for exploring local parks or enjoying leisurely strolls through the charming downtown.During this peak season, Winona buzzes with activity, attracting families and travellers keen on participating in various outdoor pursuits, such as fishing or hiking in nearby nature reserves. The community often hosts events that celebrate local music, food, and crafts, providing a lively option for visitors.If you're looking for a more budget-friendly option, consider planning your visit in November. This month offers a quieter experience, allowing you to enjoy the beauty of the autumn landscape while avoiding the crowds. You can take leisurely walks through the area and appreciate the changing foliage, making it a picturesque time for exploration.Ultimately, the best time to book a holiday rental in Winona will depend on whether you prefer the lively energy of summer or the peaceful charm of the fall season.
What are the top attractions in Winona?
In Winona, Mississippi, visitors can explore several top attractions. The historic downtown area features charming boutiques and local eateries that reflect the town's Southern hospitality. The Winona Museum offers insights into the local history and culture, showcasing exhibits that highlight the region's heritage.Nearby, Lake Gus has recreational opportunities, including fishing and picnicking, making it a lovely spot for outdoor enthusiasts. Additionally, the scenic views along the Yalobusha River provide a peaceful backdrop for nature walks and photography.
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.