Best Vacation Homes in Winona County
House
10.0(138 Reviews)
4 Bedrooms
4 Baths
10 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $445/Night
7 Nights - US $3,112
Bed & Breakfast
9.7(186 Reviews)
5 Bedrooms
5 Baths
11 Guests
404.72 ft²
- Balcony/Terrace
View- Parking
Air Conditioner
US $119/Night
7 Nights - US $833
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Pet Friendly- Parking
US $230/Night
7 Nights - US $1,610
House
10.0(58 Reviews)
5 Bedrooms
2 Baths
20 Guests
4000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $517/Night
7 Nights - US $3,616
House
9.7(3 Reviews)
3 Bedrooms
2 Baths
5 Guests
1689.93 ft²
- Fireplace/Heating
- Parking
Internet
Child Friendly
US $243/Night
7 Nights - US $1,699
House
10.0(53 Reviews)
3 Bedrooms
3 Baths
10 Guests
2000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $250/Night
7 Nights - US $1,748
House
10.0(42 Reviews)
2 Bedrooms
1 Bath
4 Guests
Spa- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $184/Night
7 Nights - US $1,285
Apartment
10.0(31 Reviews)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $117/Night
7 Nights - US $816
Winona County Luxury Rentals
Cabin
3 Bedrooms
2 Baths
12 Guests
665 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $396/Night
7 Nights - US $2,773
House
9.8(44 Reviews)
4 Bedrooms
2 Baths
13 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $384/Night
7 Nights - US $2,688
House
10.0(27 Reviews)
3 Bedrooms
1 Bath
6 Guests
1328 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $320/Night
7 Nights - US $2,238
Cottage
9.6(58 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $272/Night
7 Nights - US $1,907
Apartment
2 Bedrooms
2 Baths
5 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $260/Night
7 Nights - US $1,823
House
10.0(9 Reviews)
3 Bedrooms
1 Bath
5 Guests
1694 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $241/Night
7 Nights - US $1,690
House
1 Bedroom
1 Bath
4 Guests
505.9 ft²
- Pet Friendly
- Parking
- Child Friendly
Security/Safety
US $227/Night
7 Nights - US $1,589
Cabin
10.0(25 Reviews)
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $225/Night
7 Nights - US $1,573
Winona County Pet Friendly Vacation Rentals
Cabin
10.0(13 Reviews)
1 Bedroom
1 Bath
4 Guests
192 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $129/Night
7 Nights - US $902
House
9.6(9 Reviews)
2 Bedrooms
1 Bath
5 Guests
1001.04 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Parking
US $214/Night
7 Nights - US $1,496
Cottage
10.0(1 Review)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $169/Night
7 Nights - US $1,183
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $206/Night
7 Nights - US $1,444
House
1 Bedroom
2 Baths
8 Guests
1001.04 ft²
- Pet Friendly
- Parking
- Internet
- Child Friendly
US $165/Night
7 Nights - US $1,155
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $204/Night
7 Nights - US $1,431
Cottage
9.8(69 Reviews)
2 Bedrooms
1 Bath
5 Guests
1000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $198/Night
7 Nights - US $1,387
Cabin
9.8(16 Reviews)
1 Bedroom
1 Bath
4 Guests
192 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $125/Night
7 Nights - US $872
Winona County Large Vacation Homes
Cabin
3 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Internet
- Child Friendly
US $353/Night
7 Nights - US $2,471
Why Choose Rent By Owner for your Winona County 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 County
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can significantly enhance your experience, whether you're seeking outdoor adventures or a quiet retreat in this picturesque region.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, making it ideal for exploring the scenic beauty and outdoor activities in this region.
Average Temperature Daytime: 78°F - Nighttime: 58°F
Fall (September to November)
Autumn brings a vibrant display of fall foliage that enhances your experience here, perfect for outdoor adventures and appreciating the natural landscape.
Average Temperature Daytime: 65°F - Nighttime: 45°F
Off-Season Highlights
Winter (December to February)
In winter, the area offers a peaceful retreat with cooler temperatures, ideal for cozy stays and enjoying the quiet charm of this destination.
Average Temperature Daytime: 30°F - Nighttime: 15°F
Spring (March to May)
Spring awakens the region with blooming flora and milder temperatures, providing a lovely setting to explore nature’s renewal.
Average Temperature Daytime: 55°F - Nighttime: 35°F
Weekly Weather Forecast for Winona County
How to Book Your Winona County 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 County
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 private outdoor seating area ideal for relaxing and dining amidst scenic views.
- Take advantage of spacious yards perfect for outdoor activities or family gatherings.
- Make the most of nearby hiking and biking trails to explore the natural beauty of the region.
- Utilize outdoor fire pits for cozy evenings under the stars with friends and family.
- Benefit from access to waterfront features such as docks, boat slips, or fishing spots.
- Relax in a screened porch or patio that offers shelter while enjoying the fresh air.
- Use outdoor recreational equipment like kayaks, paddleboards, or grills provided at some properties.
Top Attractions Around Winona County
What attractions are nearby?
During your stay, you'll find a variety of outdoor activities and cultural experiences nearby, allowing you to explore the natural beauty and local heritage that this region has to offer.
Family Activities
- Winona County Family Fun Center: Enjoy lively indoor activities and arcade games perfect for family members of all ages in this popular attraction within the region.
- Sugar Loaf Bluff Park: Explore scenic hiking trails and breathtaking overlooks in this natural park, ideal for family picnics and outdoor adventures nearby your vacation rental.
- Lake Winona: Spend a relaxing day swimming, paddleboarding, or fishing on this beautiful lake, which offers numerous family-friendly water activities close to here.
- The Wabasha-Kellogg Bridge: Take a family walk across this historic bridge with picturesque views of the Mississippi River, offering an enjoyable outing just outside your vacation accommodations.
Adult Activities
- Hiking and Biking Trails: Explore extensive trail systems that wind through the scenic landscapes of the area, perfect for outdoor enthusiasts seeking adventure and nature immersion.
Other Places to Stay in Winona County, MN
New Hartford
Dakota
Dresbach
Stockton
Goodview
Lewiston
Winona
Minnesota City
Wilson
Rollingstone
St. Charles
Winona County Travel Tips
How Can You Make the Most of Your Stay?
- Plan Your Outdoor Adventures: Take advantage of the region's scenic parks and trails to explore the natural beauty that makes this destination unique.
- Discover Local Cuisine: Sample regional specialties at local eateries to experience authentic flavors throughout your stay here.
- Book Your Stay Early: Secure your preferred vacation rentals in advance, especially during peak seasons, to enjoy the best options available.
- Explore Seasonal Events: Check the area's event calendar for festivals and activities that can enrich your visit and provide a true taste of local culture.
Transportation Options
- Winona Transit Service: This local bus system provides convenient transportation within the city and surrounding areas, making it easy to explore the region without a car.
- Amtrak Rail Service: The nearby rail station connects you to major cities, offering an accessible travel option for those looking to experience scenic routes in this part of Minnesota.
- Rental Car Services: Several rental agencies operate here, giving you flexible options to explore Winona County at your own pace and visit outdoor attractions and charming towns.
- Taxi and Ride-Sharing Services: Taxis and ride-sharing apps are readily available, providing quick and reliable transportation for day trips or quick errands around the area.
Local Customs Options
- Traditional Winona County Festivals: Participating in local festivals offers a glimpse into the area's rich heritage and community spirit, making your stay more culturally immersive.
- Native American Heritage:** Recognizing and respecting the indigenous history is important when exploring this region, which has a deep-rooted Native American presence.
- Farming Traditions:** Engaging with the region's agricultural customs provides insight into the area's rural lifestyle and longstanding practices.
- Waterway Etiquette: When enjoying the lakes and rivers here, observing proper boating and fishing manners ensures a respectful experience aligned with local customs.
Winona County Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Winona County?
There are a lot of options in Winona County. If you plan on staying in the Winona County 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 County:
- Charming Brick Farmhouse with a Touch of Elegance. -Winona
- Renovated Mid-Century Modern House
- Rural Winona Co. Guest House Getaway: Relax and Enjoy the Simple Things in Life
- Quiet Cottage in the Valley with Outdoor Sauna
- Entire cozy Rollingstone apt in Mississippi Valley, just 10 min from Winona!
- Vintage Lustron Home Piece of History
- Quaint, quite, affordable cute cabin snuggled in a beautiful valley!
- Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
- Martha's Place
- Treehouse Cabin in the Bluff Woodlands South
2. Which vacation homes in Winona County are best for families?
If you are looking for a family-friendly vacation home in Winona County, 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 County:
3. How many Rentbyowner vacation rentals are available in Winona County?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 77 in the Winona County 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 County.
4. What is the cancellation policy typically associated with vacation rentals in Winona County?
Cancellation policies vary by listing, so it’s important to review the specific terms provided by the property owner before booking your stay in this area.
5. How do I contact the property owner for special requests or questions about my booking in this region?
You can reach out directly through the messaging system provided on the booking platform to communicate any special needs or inquiries about your vacation rental here.
6. Are there any additional fees or deposits required when booking in this destination?
Many properties in the region may require security deposits or cleaning fees; details are listed with each property, so be sure to check the listing for the exact costs.
7. What amenities are usually included in vacation rentals around here?
Amenities vary by property but often include essentials like Wi-Fi, kitchen facilities, and outdoor spaces. Specific features are detailed within each listing, allowing you to choose accordingly.
8. Is there a minimum stay requirement when booking in this part of the region?
Minimum stay requirements depend on the individual property and can differ depending on the time of year or availability; please review the booking policies listed for each property.
Winona County Top Rated Vacation Rentals
Hotel
9.4(376 Reviews)
1 Bath
Hot Tub
Pool
Breakfast- Kitchen
US $160/Night
7 Nights - US $1,118
Hotel
9.2(912 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Breakfast
US $116/Night
7 Nights - US $813
US $136/Night
7 Nights - US $950
Hotel
8.9(171 Reviews)
10 Baths
322.92 ft²
Private Pool- Fireplace/Heating
- Pool
- Pet Friendly
US $172/Night
7 Nights - US $1,201
US $162/Night
7 Nights - US $1,133
Hotel
8.6(1002 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $134/Night
7 Nights - US $938
Hotel
8.5(160 Reviews)
9 Baths
355.21 ft²
- Private Pool
Oceanfront- Hot Tub
- Fireplace/Heating
US $139/Night
7 Nights - US $970
Hotel
8.1(80 Reviews)
1 Bath
333.68 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $166/Night
7 Nights - US $1,159
