Best Vacation Homes in Winona
10 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $608/Night
For 7 Nights CA $4,257
1689.93 ft²
5 Guests
3 Bedrooms
2 Bathrooms
House
- Fireplace/Heating
- Parking
- Internet
CA $332/Night
For 7 Nights CA $2,324
1 Bedroom
1 Bathroom
Couples Retreat
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $315/Night
For 7 Nights CA $2,202
1500 ft²
5 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
CA $269/Night
For 7 Nights CA $1,886
404.72 ft²
11 Guests
5 Bedrooms
5 Bathrooms
Bed & Breakfast
- Balcony/Terrace
- View
- Parking
CA $163/Night
For 7 Nights CA $1,139
4000 ft²
20 Guests
5 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $662/Night
For 7 Nights CA $4,637
2000 ft²
10 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $327/Night
For 7 Nights CA $2,288
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Spa
- Fireplace/Heating
- Balcony/Terrace
CA $244/Night
For 7 Nights CA $1,711
Winona Luxury Rentals
1328 ft²
6 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $437/Night
For 7 Nights CA $3,061
1496.18 ft²
6 Guests
3 Bedrooms
1 Bathroom
Free Cancellation
Apartment
- Fireplace/Heating
- Parking
- Internet
CA $404/Night
For 7 Nights CA $2,825
947.22 ft²
6 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Villa
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $373/Night
For 7 Nights CA $2,610
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $373/Night
For 7 Nights CA $2,608
5 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Fireplace/Heating
- Air Conditioner
- Internet
CA $356/Night
For 7 Nights CA $2,494
495.14 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Pet Friendly
- Parking
- Child Friendly
CA $311/Night
For 7 Nights CA $2,174
1694 ft²
5 Guests
3 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
CA $289/Night
For 7 Nights CA $2,020
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Kitchen
- Parking
CA $249/Night
For 7 Nights CA $1,745
Winona Pet Friendly Vacation Rentals
1000 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $141/Night
For 7 Nights CA $989
1001.04 ft²
8 Guests
1 Bedroom
2 Bathrooms
House
- Pet Friendly
- Parking
- Internet
CA $226/Night
For 7 Nights CA $1,580
500 ft²
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $236/Night
For 7 Nights CA $1,654
322.92 ft²
10 Bathrooms
Family Friendly
Hotel
- Private Pool
- Fireplace/Heating
- Pool
CA $235/Night
For 7 Nights CA $1,643
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cabin
- Pet Friendly
- Child Friendly
- Security/Safety
CA $135/Night
For 7 Nights CA $948
355.21 ft²
9 Bathrooms
Free Cancellation
Hotel
- Private Pool
- Oceanfront
- Hot Tub
CA $190/Night
For 7 Nights CA $1,327
333.68 ft²
1 Bathroom
Ocean View
Hotel
- Private Pool
- Oceanfront
- Hot Tub
CA $229/Night
For 7 Nights CA $1,600
312.15 ft²
6 Bathrooms
Free Cancellation
Hotel
- Fireplace/Heating
- Pet Friendly
- Parking
CA $201/Night
For 7 Nights CA $1,405
Winona Top Rated Vacation Rentals
CA $184/Night
For 7 Nights CA $1,289
CA $159/Night
For 7 Nights CA $1,112
CA $191/Night
For 7 Nights CA $1,336
CA $191/Night
For 7 Nights CA $1,336
1 Bathroom
Family Friendly
Hotel
- Hot Tub
- Fireplace/Heating
- Pool
CA $153/Night
For 7 Nights CA $1,068
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?
Timing your visit to the area is key to enjoying your stay, so consider planning your trip during the most favorable seasons for weather and local events in this picturesque destination.
Peak Season Highlights
Summer (June to August)
Experience warm weather and vibrant outdoor activities during the peak summer months, perfect for exploring the scenic landscapes of this destination.
Average Temperature Daytime: around 80°F (27°C) - Nighttime: around 60°F (16°C)
Fall (September to November)
Enjoy the breathtaking fall foliage as the region transforms with colorful leaves, making it an ideal time for scenic drives and outdoor adventures.
Average Temperature Daytime: around 70°F (21°C) - Nighttime: around 45°F (7°C)
Off-Season Highlights
Winter (December to February)
The area quiets down during the winter months, offering a peaceful retreat with chances for winter sports and cozy stays in your vacation rental.
Average Temperature Daytime: around 30°F (-1°C) - Nighttime: around 15°F (-9°C)
Spring (March to May)
Springtime brings milder weather and blooming scenery, providing a refreshing backdrop for those seeking a less crowded visit.
Average Temperature Daytime: around 55°F (13°C) - Nighttime: around 35°F (2°C)
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 spacious outdoor decks or patios perfect for relaxing and entertaining.
- Take advantage of private gardens or lush yard spaces to immerse yourself in the natural surroundings.
- Make use of outdoor grilling areas to prepare meals while enjoying the fresh air.
- Benefit from access to nearby parks or scenic walking trails for outdoor exploration.
- Relax by a private or community fire pit, ideal for evening gatherings under the stars.
- Utilize designated bike paths or storage for your biking adventures around this region.
- Admire picturesque views from outdoor seating areas that showcase the area’s scenic beauty.
Top Attractions Around Winona
What attractions are nearby?
Here, you can explore scenic hiking trails, enjoy local art galleries, and experience outdoor water activities just moments from your vacation rentals in Winona, Minnesota, offering a perfect blend of relaxation and adventure in the region.
Family Activities
- Winona National Wildlife Refuge: Explore the region’s natural beauty by observing local bird species and walking along scenic trails suitable for the whole family.
- Garvin Heights Lookout: Take a short drive to this popular vantage point for breathtaking panoramic views of the area, perfect for family photos and outdoor fun.
- Minnesota Marine Art Museum: Introduce your family to inspiring artwork and engaging exhibits that highlight the region's rich cultural heritage and artistic history.
- Lake Winona Recreation Area: Enjoy outdoor activities such as paddle boating, fishing, or picnicking at this family-friendly spot in the area’s vibrant lake district.
Adult Activities
- Winona State University Campus Tours: Discover the vibrant academic atmosphere and historic architecture by exploring the campus, offering a unique glimpse into the heart of this university town.
- Historic Downtown Winona:** Enjoy strolling through charming streets filled with boutique shops, local cafes, and art galleries that showcase the area's rich cultural heritage.
- Mississippi River Cruises:** Experience the region from a different perspective by taking scenic boat cruises along the nearby Mississippi River, revealing stunning natural beauty and tranquility.
- Wabasha Street Caves Tour:** Delve into the fascinating history of these underground caves with guided tours that highlight their past uses and significance within this destination.
Other Places to Stay in Winona, MN
Stockton
Wiscoy
Goodview
Winona County
Garvin Heights City Park
Garvin Heights Vineyard
Lake Park
Lake Lodge Recreation Center
Winona State University
Historic Downtown Winona
Minnesota Marine Art Museum
Wilson
Winona Travel Tips
How Can You Make the Most of Your Stay?
- Plan your visit during the local festivals or seasonal events: Attending these gatherings enhances your experience and offers authentic insights into the area's culture and community.
- Explore outdoor activities in natural settings: Take advantage of nearby parks, trails, or waterfronts to immerse yourself in the region’s scenic beauty and enjoy active pursuits.
- Book your stay well in advance: Securing your vacation rentals early ensures access to the most desirable properties and gives you ample time to plan your itinerary.
- Research local dining and entertainment options: Discover charming eateries and cultural venues around here to enrich your visit and support local businesses.
Transportation Options
- Winona Transit Service: This local bus system offers convenient transportation throughout the area, making it easy to explore your surroundings during your stay.
- Rental Cars: Numerous car rental agencies are available here, providing flexible options for exploring beyond the city with ease.
- Taxi Services and Rideshares: Taxis and rideshare providers like Uber and Lyft operate in this region, offering quick and reliable transit for any travel plans.
- Bike Rentals and Trails: Biking is a popular way to get around here, with several bike rental shops and scenic trails perfect for active exploration.
Local Customs Options
- Local Craftsmanship: You can observe and appreciate the region’s rich tradition of handcrafted goods, which reflect the area's artistic heritage.
- Community Festivals: Participating in seasonal festivals offers a glimpse into local customs and the warm, welcoming spirit of the community.
- Historic Preservation: Respect for historic sites and architecture is a key part of the region's pride, offering opportunities to learn about its past.
- Outdoor Recreation Etiquette: When exploring scenic areas, you'll find that outdoor activities like hiking and boating are embraced with an emphasis on environmental stewardship and safety.
Frequently Asked Questions About Winona?
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:
- Charming Brick Farmhouse with a Touch of Elegance. -Winona
- Family friendly in the peaceful heart of town
- 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
- Charming 3-bedroom, 2 bathroom house with outdoor space in Winona
- Charming Home: 3 Blocks to Winona State University
- The Exchange 12 | Historic Bldg, 1 BR ADA, Dwntwn
- Charming Home 3 Blocks to Winona State University
- Big River Escape Parkside Bungalow
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 46 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 Winona, Minnesota?
Cancellation policies vary depending on the specific property listing. You should review the cancellation terms on the property page or contact the owner directly to understand the refund options and any applicable fees before booking.
5. Are there any additional fees I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning charges, service fees, or security deposits can vary by property. Details are typically listed on the booking page, so be sure to read the full description or reach out to the host for clarification.
6. How do I check the availability of vacation rentals in this destination?
Availability depends on the specific property and dates you choose. Use the booking calendar on the listing to see real-time availability or contact the property owner if you have specific dates in mind.
7. What amenities are usually included in vacation rentals here?
Amenities vary between properties but often include essentials like Wi-Fi, parking, and fully equipped kitchens. To see what’s included, refer to the property description or ask the owner directly during your inquiry.
8. How do I contact the property owner or manager if I have questions about my stay?
You can communicate with the owner or manager through the messaging system provided on the booking platform. For urgent inquiries, look for contact details on the listing or reach out via the contact options listed.
