Compare vacation rentals in Winona, MN from 100+ sites!

91 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Winona, MN vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Winona, MN

Best family friendly Winona, MN vacation rentals

Among the 91 accommodations in Winona, MN, here are the 4 best family friendly rentals

Quiet Private Apartment Walkable To Wsu - Winona, MN
9.9 298 reviews

Quiet Private Apartment Walkable To Wsu

apartment, Winona
This Winona apartment is conveniently located near Winona State University and Cotter High School, making it a great option for students, families visiting students, or anyone exploring the area. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
This rental features a private entrance and a lockable door, accommodating up to two guests. Guests can enjoy a fully equipped kitchen, in-unit laundry, comfortable amenities like a queen-size bed, a Smart TV with Netflix, and a workspace, as well as entertainment options like board games and books.
Cottage By Lake Winona - Winona, MN
9.8 189 reviews

Cottage By Lake Winona

cottage, Winona
The Cottage by Lake Winona is located in Winona, Minnesota, just 10 blocks from the Mississippi River and downtown, offering easy access to both natural beauty and urban amenities. This vacation rental has received excellent ratings for its cleanliness, location, and overall user experience.
The 3-bedroom cottage comfortably sleeps 6 guests, making it ideal for families or groups of friends. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking, along with stunning lake views, making it a perfect base for exploring Winona and enjoying its natural surroundings.
Lower Level Oasis - Suite #2 - Heart Of Winona - Winona, MN
10 293 reviews

Lower Level Oasis - Suite #2 - Heart Of Winona

apartment, Winona
This charming basement apartment is located in a historic home just a few blocks from downtown Winona, offering easy access to shops, restaurants, and entertainment. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
This cozy rental is perfect for a small family or group of friends, accommodating up to three guests. The apartment includes a fully-equipped kitchen with stainless steel appliances, a comfortable living room with a large TV, a luxurious bathroom with a soaking tub, and a private laundry area.
Vintage Lustron Home Piece Of History - Winona, MN
10 33 reviews

Vintage Lustron Home Piece Of History

apartment, Minnesota City
This charming vintage home is located in Minnesota City, just a short distance from the Mississippi River, Aghaming Park And Preserve, and the Polish Cultural Institute & Museum Annex, offering a peaceful and scenic setting. The apartment consistently receives excellent ratings from guests, highlighting its comfortable and welcoming atmosphere.
This two-bedroom rental can comfortably accommodate up to six guests, providing ample space for families or groups of friends. Enjoy a fully equipped kitchen, air conditioning, a private terrace, and a cozy fireplace, along with access to nearby hiking trails, fishing spots, and the vibrant city of Winona, just a short drive away.

Best pet friendly Winona, MN vacation rentals

Among the 91 accommodations in Winona, MN, here are the 1 best pet friendly rentals

The Chateau On Butterfly Trail - 6 Bdrm Retreat - Winona, MN
No reviews

The Chateau On Butterfly Trail - 6 Bdrm Retreat

house, Dodge
This spacious country house is located in Fountain City, 11 miles from Wesley United Methodist Church and Levee Park, and 16 miles from Perrot State Park.
This 3610 square foot estate accommodates up to 35 guests with six bedrooms, three bathrooms, a fully equipped kitchen, air conditioning, free WiFi, and barbecue facilities, offering proximity to skiing and a garden with an outdoor fireplace.

Frequently Asked Questions about vacation rentals in Winona, MN

  • What are the must-see sights in Winona, Minnesota?

    Winona boasts some fantastic sights! The iconic Sugar Loaf, a bluff overlooking the Mississippi River, offers breathtaking views and is a popular hiking spot. Downtown Winona itself is charming, with its historic architecture and the beautiful Winona State University campus. The Minnesota Marine Art Museum is a must-visit for art lovers, showcasing a remarkable collection of maritime art. And don't forget the Trempealeau National Wildlife Refuge just across the river in Wisconsin – a quick trip for stunning natural beauty.
  • What are the best Airbnb and vacation rentals in Winona, MN?

    ~ Third Street Suites ~ #11, Penthouse Retreat-near Downtown Winona and ~ Third Street Suites ~ #10 are the most popular Airbnb and vacation rentals in Winona, MN among travelers.

  • Are there unique natural phenomena in Winona, Minnesota?

    Yes! The Mississippi River itself is a major natural feature, shaping the landscape and offering opportunities for boating, fishing, and enjoying the river bluffs. The Sugar Loaf bluff provides a unique geological formation, while the Trempealeau National Wildlife Refuge showcases diverse plant and animal life. The river's changing water levels and the seasonal shifts in the surrounding landscape also create a dynamic and ever-changing natural environment.
  • What are the most popular Airbnbs in Winona, MN?

    Among the Airbnbs in Winona, MN, ~ Third Street Suites ~ #11, Penthouse Retreat-near Downtown Winona and ~ Third Street Suites ~ #10 are the most popular ones.

  • What essentials should you bring along for a trip to Winona, Minnesota?

    Comfortable walking shoes are a must, as Winona is best explored on foot. Layers of clothing are recommended, as the weather can be unpredictable. Sunscreen and insect repellent are also good ideas, especially during the warmer months. A camera is essential to capture the stunning views and charming architecture. And finally, don't forget a reusable water bottle to stay hydrated while exploring.
  • What are the best vacation rentals with a pool in Winona, MN?

    The best vacation rental with a pool in Winona, MN is 6bdrm/2bath Duplex-2 Story Home.

  • What famous events or festivals are happening in Winona, Minnesota?

    Winona hosts several events throughout the year. The Great River Shakespeare Festival is a popular summer attraction, showcasing classic and contemporary plays. The annual Applefest celebration features apple-related treats and activities. Check local listings for other smaller festivals and events that might coincide with your visit.
  • What are the best rentals for families and kids in Winona, MN?

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Winona, Minnesota?

    A daily budget of $150-$300 per person should cover most expenses. This is an estimate and can vary greatly depending on your accommodation choices (ranging from budget-friendly motels to upscale hotels), dining preferences (from casual eateries to fine dining), and choice of activities. Transportation costs within Winona are relatively low, especially if you walk or bike.
  • What are the best rentals or Airbnbs with a jacuzzi in Winona, MN?

    Family Friendly In The Peaceful Heart Of Town and Penelope's Place are the best vacation rentals or Airbnb with a jacuzzi in Winona, MN.

  • Where can you find the best restaurants serving local dishes in Winona, Minnesota, and what are the must-try specialties?

    Winona has a diverse culinary scene. The Winona Brewing Company offers local brews and pub fare. For something more upscale, try Latsch's Tavern for classic American dishes. Many restaurants feature seasonal dishes that highlight local ingredients. Be sure to try some of the regional specialties, such as walleye (a type of freshwater fish) and hearty Midwestern comfort food.
  • What are some less-famous attractions in Winona, Minnesota that are worth a visit?

    The Winona History Center offers a glimpse into the city's past. The Garvin Heights Scenic Drive provides beautiful views of the Mississippi River Valley. Exploring the many parks and trails along the riverfront offers a chance to appreciate the natural beauty of the area. The Amish community near Winona offers a unique cultural experience, though respecting their privacy is paramount.
  • What are the best activities for engaging with locals and understanding their culture in Winona, Minnesota?

    Visiting local farmers' markets allows you to interact with residents and sample local produce. Attending a performance at the historic Winona State University offers a chance to experience the local arts scene. Striking up conversations with people at local businesses or cafes can provide insights into the community's character. Simply exploring the downtown area and observing everyday life will give you a feel for the local atmosphere.
  • What unique natural landscapes and terrain features can travelers explore in Winona, Minnesota?

    The Mississippi River Valley's bluffs, offering stunning overlooks and hiking trails, are a key feature. The river itself provides opportunities for kayaking, canoeing, and fishing. The Trempealeau National Wildlife Refuge, across the river in Wisconsin, offers diverse habitats and wildlife viewing opportunities. These varied landscapes, from riverfront to blufftop, offer diverse experiences.
  • How many days are ideal for visiting Winona, Minnesota, and what are some itinerary suggestions?

    Two to three days is a good amount of time to explore Winona. Day 1 could focus on downtown, the Minnesota Marine Art Museum, and the Sugar Loaf. Day 2 could involve exploring the riverfront, perhaps with a boat tour or hike. Day 3 could be dedicated to the Trempealeau National Wildlife Refuge or a visit to the Winona History Center. Adjust this based on your interests.
  • How is the weather in Winona, Minnesota in high season?

    Winona's high season is generally summer (June-August), with warm temperatures averaging in the 70s°F (low to mid 20s°C), though it can be hotter. Expect some humidity. Spring and fall offer pleasant temperatures, but be prepared for some rain. Winters are cold, with snow and ice common.

Nearby regions

Best Winona, MN vacation rentals with a pool

Among the 91 accommodations in Winona, MN, here are the 1 best rentals with a pool

Studio King With Kitchenette-44° North - Winona, MN
No reviews

Studio King With Kitchenette-44° North

studio, Winona
This studio offers a prime downtown Winona location, placing you within walking distance of numerous downtown attractions and landmarks.
This elegant suite accommodates up to two guests and features a kitchenette, air conditioning, and access to a swimming pool, jacuzzi, fitness center, and parking.

Best Winona, MN vacation rentals with parking

Hawks View's Goshawk Cottage - Winona, MN
No reviews

Hawks View's Goshawk Cottage

house, Fountain City
Hawks View's Goshawk Cottage is located in Fountain City, 37 miles from La Crosse Municipal Airport.
This 1050 square foot country house accommodates up to 3 guests with 2 bedrooms and 1 bathroom, featuring a fridge, microwave oven, air conditioning, internet, a fireplace, hammam, and a barbecue area, with paid on-site private parking available.
Hawks View's Cooper’s Hawk Cottage - Winona, MN
No reviews

Hawks View's Cooper’s Hawk Cottage

house, Fountain City
Hawks View's Cooper’s Hawk Cottage is a country house located in Fountain City, approximately 37 miles from La Crosse Municipal Airport.
This one-bedroom, one-bathroom cottage offers 1050 square feet of living space, accommodates up to 3 guests, and features a kitchenette with a fridge and microwave, air conditioning, WiFi, a hammam, and barbecue area, with paid on-site parking available.
Cottage By Lake Winona - Winona, MN
9.8 189 reviews

Cottage By Lake Winona

cottage, Winona
The Cottage by Lake Winona is located in Winona, Minnesota, just 10 blocks from the Mississippi River and downtown, offering easy access to both natural beauty and urban amenities. This vacation rental has received excellent ratings for its cleanliness, location, and overall user experience.
The 3-bedroom cottage comfortably sleeps 6 guests, making it ideal for families or groups of friends. Amenities include a fully equipped kitchen, air conditioning, a garden, and parking, along with stunning lake views, making it a perfect base for exploring Winona and enjoying its natural surroundings.
Hawks View's Marsh Hawk Cottage - Winona, MN
No reviews

Hawks View's Marsh Hawk Cottage

house, Fountain City
Hawks View's Marsh Hawk Cottage is located in Fountain City, approximately 37 miles from La Crosse Municipal Airport.
This one-bedroom, one-bathroom vacation rental offers 1050 square feet of living space for up to three guests, featuring a kitchenette with a fridge and microwave, air conditioning, WiFi, a hammam, and an outdoor barbecue.
©2026 cozycozy.com