Best Vacation Homes in Winona
House
10.0(23 Reviews)
2 Bedrooms
1 Bath
6 Guests
Fireplace/Heating
Balcony/Terrace
Pet Friendly
Kitchen
US $169/Night
7 Nights - US $1,185
Cabin
10.0(18 Reviews)
2 Bedrooms
1 Bath
8 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $163/Night
7 Nights - US $1,140
House
10.0(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
Parking
US $283/Night
7 Nights - US $1,980
Apartment
10.0(4 Reviews)
2 Bedrooms
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $217/Night
7 Nights - US $1,522
Cabin
9.8(145 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Kitchen
- Parking
Air Conditioner
US $137/Night
7 Nights - US $962
Cabin
9.8(58 Reviews)
2 Bedrooms
1 Bath
6 Guests
900 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $304/Night
7 Nights - US $2,126
Cabin
9.8(55 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $143/Night
7 Nights - US $1,001
Cabin
9.8(40 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $147/Night
7 Nights - US $1,032
Winona Luxury Rentals
New
Cabin
11 Bedrooms
12 Baths
41 Guests
12500 ft²
- Fireplace/Heating
Pool- Kitchen
- Parking
US $2,125/Night
7 Nights - US $14,875
House
9.6(8 Reviews)
3 Bedrooms
3 Baths
16 Guests
4500 ft²
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $544/Night
7 Nights - US $3,811
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $501/Night
7 Nights - US $3,504
House
8.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
Internet
Child Friendly
US $446/Night
7 Nights - US $3,119
House
10.0(5 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $410/Night
7 Nights - US $2,867
House
8.8(28 Reviews)
6 Bedrooms
1 Bath
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $410/Night
7 Nights - US $2,867
Cabin
9.8(46 Reviews)
3 Bedrooms
1 Bath
10 Guests
1828 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $317/Night
7 Nights - US $2,220
House
10.0(78 Reviews)
3 Bedrooms
2 Baths
6 Guests
1400 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $260/Night
7 Nights - US $1,819
Winona Pet Friendly Vacation Rentals
Cabin
9.6(26 Reviews)
1 Bedroom
1 Bath
4 Guests
700 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $130/Night
7 Nights - US $910
Cabin
8.2(10 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Child Friendly
US $250/Night
7 Nights - US $1,753
House
10.0(113 Reviews)
3 Bedrooms
1 Bath
5 Guests
830 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $186/Night
7 Nights - US $1,300
Cabin
10.0(21 Reviews)
3 Bedrooms
1 Bath
11 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $247/Night
7 Nights - US $1,727
Cabin
9.2(10 Reviews)
3 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $166/Night
7 Nights - US $1,160
House
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $231/Night
7 Nights - US $1,617
New
Cabin
1 Bedroom
1 Bath
2 Guests
398 ft²
- Pet Friendly
- Kitchen
- Parking
- Air Conditioner
US $116/Night
7 Nights - US $809
House
9.6(65 Reviews)
2 Bedrooms
1 Bath
5 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $131/Night
7 Nights - US $917
Winona Large Vacation Homes
Villa
9.6(5 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $134/Night
7 Nights - US $938
House
4.6(12 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Child Friendly
US $209/Night
7 Nights - US $1,463
Why Choose Rent By Owner for your Winona Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Winona
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination ensures you can enjoy its unique charm and natural beauty, making your stay in the area truly memorable.
Peak Season Highlights
Spring (March to May)
During spring, you can enjoy pleasant weather and vibrant natural scenery, making it an ideal time for outdoor activities in this region.
Average Temperature Daytime: 60°F to 75°F - Nighttime: 40°F to 55°F
Fall (September to November)
Autumn offers cooler temperatures and colorful foliage, perfect for exploring the scenic landscapes and enjoying outdoor attractions.
Average Temperature Daytime: 65°F to 70°F - Nighttime: 45°F to 50°F
Off-Season Highlights
Summer (June to August)
While summer has warmer weather, it tends to be busier with visitors seeking outdoor adventures and festivals in the area.
Average Temperature Daytime: 80°F to 90°F - Nighttime: 60°F to 70°F
Winter (December to February)
This season is typically quieter, offering a peaceful retreat with colder temperatures that are suitable for cozy stays and indoor activities.
Average Temperature Daytime: 30°F to 45°F - Nighttime: 15°F to 25°F
Weekly Weather Forecast for Winona
How to Book Your Winona Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Winona
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a spacious outdoor patio or deck perfect for relaxing and dining al fresco.
- Take advantage of a private or shared fire pit to gather around on cool evenings.
- Benefit from access to scenic hiking trails or nature walks nearby, ideal for exploring the region’s natural beauty.
- Make use of a fully equipped outdoor grilling area to prepare meals during your stay.
- Relax in a charming gazebo or outdoor lounge area designed for unwinding outdoors.
- Spend time by a peaceful pond or lake that offers opportunities for fishing or kayaking in the vicinity.
- Utilize designated parking areas with convenient outdoor access, making it easier to enjoy all the outdoor amenities.
Top Attractions Around Winona
What attractions are nearby?
In this destination, you can enjoy a variety of outdoor activities such as exploring scenic parks, hiking trails, and fishing spots that showcase the natural beauty of the region nearby your vacation rentals.
Family Activities
- Wappapello Lake Recreation Area: Enjoy family-friendly activities like boating, fishing, and picnicking along the scenic shores here.
- Fort Davidson State Historic Site: Step back in time with educational tours and explore Civil War history at this engaging local landmark.
- Lake Wappapello State Park: Experience outdoor adventure with hiking trails, swimming areas, and camping options perfect for a family getaway.
- Indian Mound Recreation Area: Discover nature through peaceful walking trails and open spaces ideal for outdoor family fun and exploration.
Adult Activities
- Fishing at Lake Winona: You can enjoy a relaxing day casting your line and experiencing the region’s tranquil waters just outside town.
- Hiking the Ozark Trail: Explore scenic routes through the nearby Ozark region, perfect for outdoor enthusiasts seeking adventure and natural beauty.
- Visiting local wineries: Discover charming wineries around here that offer tastings and tours, providing a taste of the area's flourishing wine scene.
- Exploring historic sites: Immerse yourself in the region’s history by visiting notable local landmarks and museums that tell the story of this destination’s rich past.
Other Places to Stay in Winona, MO
Rocky Falls
Winona Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Events: Check the area's calendar to align your stay with local festivals or events that highlight the region's unique culture and charm.
- Explore Nearby Nature: Take advantage of the region’s outdoor spaces by scheduling visits to nearby parks and natural attractions during your vacation rental stay.
- Discover Authentic Dining: Seek out locally recommended eateries to experience regional flavors that enhance your visit's authenticity.
- Customize Your Itinerary: Use your vacation rental as a comfortable base to tailor your activities, ensuring you enjoy both relaxation and adventure here.
Transportation Options
- Winona Transit System: This local bus service offers convenient transportation options within the area, making it easy for you to explore nearby attractions during your stay.
- Personal Vehicle Rental: Renting a car provides flexibility and comfort, allowing you to navigate the scenic region at your own pace and access remote spots with ease.
- Taxi Services: Taxi providers operate in this destination, offering reliable point-to-point transportation for quick trips around town or to the regional highlights.
- Ride-Sharing Options: Service apps are available here, giving you an effortless way to get around without the need for a personal vehicle, ideal for short trips and city excursions.
Local Customs Options
- Community Festivals: Participating in local festivals is a cherished tradition here, offering you a chance to experience the region’s vibrant culture firsthand.
- Southern Hospitality: Expect warm welcomes and friendly gestures as the locals take pride in their welcoming attitude toward visitors.
- Traditional Cuisine: Sampling regional dishes during your stay allows you to enjoy the authentic flavors that define this area’s culinary heritage.
- Respect for Nature: Visiting natural sites with an emphasis on conservation reflects the community's deep respect for the region’s outdoor beauty.
Winona Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Winona?
There are a lot of options in Winona. If you plan on staying in the Winona area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Winona:
- Unique cabins in the woods Not friendly for Street Bikes.
- Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
- Newly renovated early 1900’s farmhouse
- Unbeatable convenience in amazing Eminence!
- “The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.
- The Cottage Room has 2 queen beds and private bathroom
- Deadwood acres cabin #3
- Adorable, cozy home in the Ozark Scenic Riverways ready for a weekend get-a-away
- Barn by The Creek- Barn turned bnb in Eminence; sleeps 10
- On Main Street 1 mile from Jacks Fork River! Central Eminence location!
2. Which vacation homes in Winona are best for families?
If you are looking for a family-friendly vacation home in Winona, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Winona:
3. How many Rentbyowner vacation rentals are available in Winona?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 49 in the Winona area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Winona.
4. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the individual property listing. You should review the specific cancellation terms listed with your chosen rental or contact the owner directly for detailed information.
5. How do I confirm my reservation and what details are needed?
Reservation confirmation typically requires you to complete the booking process online by providing necessary personal and payment information. Always check the listing for any additional requirements the host might have.
6. Are there any restrictions or house rules I should be aware of when staying at a vacation rental here?
House rules and restrictions are specified within each listing. It's important to read these carefully before booking to ensure a smooth stay and compliance with the host’s guidelines.
7. What amenities are usually included in vacation rentals in this part of the region?
Amenities can vary between properties, but common features include Wi-Fi, kitchen facilities, parking, and outdoor spaces. Specific amenities are detailed in each listing, so review them closely before booking.
8. How do I inquire about availability or special requests for a rental property?
You can message the property owner directly through the booking platform to check availability or discuss any special requests. It’s recommended to communicate early to ensure accommodations meet your needs.
Winona Top Rated Vacation Rentals
Other
9.4(23 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $182/Night
7 Nights - US $1,274
Other
9.2(24 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $137/Night
7 Nights - US $962
Other
9.0(18 Reviews)
1 Bedroom
1 Bath
3 Guests
1 ft²
- Pool
Breakfast- Kitchen
- Parking
US $141/Night
7 Nights - US $986
