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Winona, MN vacation rentals
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Best Vacation rentals and Airbnb offers in Winona, MN

Best family friendly Winona, MN vacation rentals

Among the 52 accommodations in Winona, MN, here are the 4 best family friendly rentals

This Amazing River Getaway Is Perfect For You!  Private Deck, Grill & Fire Pit! - Winona, MN
9.8 7 reviews
Winona, MN
09/25 – 09/27
$470/nighttotal: $940 (2 )

This Amazing River Getaway Is Perfect For You! Private Deck, Grill & Fire Pit!

3 4
apartment , Winona
This charming Winona apartment is located just a minute's walk from the Mississippi River and 15 minutes from Merchants Bank, offering easy access to scenic walks, riverfront activities, and nearby attractions. The apartment is perfect for families or groups of up to 10 guests, with 3 bedrooms and 1 bathroom.
The apartment is fully equipped with a kitchen, laundry facilities, and comfortable amenities like linens, an ironing board, and a dining table. You can enjoy outdoor meals and relaxation in the dining area with a barbecue.
Bluffside Cottage With Gorgeous Views - Winona, MN
9.9 185 reviews
Winona, MN
08/11 – 08/12
$263/nightfor 1 night

Bluffside Cottage With Gorgeous Views

1 4
apartment , Fountain City
Hill Street House is located on a bluff overlooking the Mississippi River in Fountain City, within walking distance of the downtown area and just 10 minutes from Winona. The accommodation has received excellent ratings for location, cleanliness, and user experience.
The apartment has two bedrooms, one bathroom, and can comfortably accommodate four guests. The house offers a private deck with river views, a terraced yard with a fire pit, a fully equipped kitchen, a cozy living room, a separate office, laundry facilities, and a variety of games, books, puzzles, and entertainment options.
~ Third Street Suites ~ #7 - Winona, MN
10 312 reviews
Winona, MN
08/11 – 08/12
$239/nightfor 1 night

~ Third Street Suites ~ #7

1 4
apartment , Winona
This two-bedroom, two-level penthouse apartment in downtown Winona, Minnesota offers stunning views and is within walking distance of the Mississippi River, Lake Winona, Winona State University, the Minnesota Marine Art Museum, and the Shakespeare Festival.
The 1200-square-foot unit sleeps four guests comfortably and features a fully equipped kitchen with stainless steel appliances, a 58-inch 4K Smart TV, high-speed Wi-Fi, in-unit laundry, and soundproofing for a peaceful stay.
Vintage Lustron Home Piece Of History - Winona, MN
10 31 reviews
Winona, MN
08/11 – 08/12
$241/nightfor 1 night

Vintage Lustron Home Piece Of History

2 4
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 52 accommodations in Winona, MN, here are the 4 best pet friendly rentals

Riverview Apartment - River Road Historic Home - Winona, MN
9.7 254 reviews
Winona, MN
09/25 – 09/27
$861/nighttotal: $1722 (2 )

Riverview Apartment - River Road Historic Home

1 4
apartment , Fountain City
This Victorian home is located on the Great River Road in Fountain City, Wisconsin, just 35 miles from La Crosse Municipal Airport, offering a peaceful setting with easy access to local attractions. Guests consistently rate the property excellent for its cleanliness, location, and overall experience.
The home features comfortable bedrooms, a fully equipped kitchen with modern appliances, and a private terrace or balcony. Enjoy free Wi-Fi, parking, and a relaxing garden, perfect for enjoying the beautiful surroundings and exploring the nearby historic Fountain City Mill and the Mississippi River.
Spacious Retreat For 1-8 Guests - Winona, MN
9.9 202 reviews
Winona, MN
09/25 – 09/27
$263/nighttotal: $526 (2 )

Spacious Retreat For 1-8 Guests

1 4
apartment , Winona
This Winona rental is conveniently located near the city's outdoor recreation, shopping, and hospital, making it easy to explore everything the area has to offer. The apartment has consistently earned excellent ratings from previous guests for its cleanliness, location, and overall experience. This cozy home offers 3 bedrooms and 1 bathroom, comfortably accommodating up to 8 guests. The apartment features a fully fenced-in yard, modern amenities, and a kitchen with a fridge and microwave oven, ensuring a comfortable and convenient stay.
The Guest House - Winona, MN
10 34 reviews
Winona, MN
08/11 – 08/12
$160/nightfor 1 night

The Guest House

1 4
apartment , Winona
This modern, updated one-bedroom condo in Winona is located near the East End Fire Station, providing easy walking access to downtown Winona's dining and attractions, as well as its lakes and trails.
This pet-friendly rental offers a full kitchen with a dishwasher, air conditioning, a garden, parking, and a workspace, comfortably accommodating up to two guests with its queen Murphy bed and pull-out couch in the living room.
~ 71 Johnson Street ~ - Winona, MN
10 248 reviews
Winona, MN
09/25 – 09/27
$611/nighttotal: $1222 (2 )

~ 71 Johnson Street ~

1 4
apartment , Winona
This apartment is located in downtown Winona, just steps away from the Mississippi Riverfront, coffee shops, restaurants, bars, Winona State University, and Lake Winona. It has excellent ratings for location, cleanliness, and user experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to eight guests. It features a full kitchen with stainless steel appliances, a comfortable living room, a private patio, free Wi-Fi, Hulu Live TV, a Roku Smart TV, brown noise sleep speakers, and a stacked laundry unit.

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 52 accommodations in Winona, MN, here are the 2 best rentals with a pool

Walkable Retreat In A Historic Neighborhood - Winona, MN
10 2 reviews
Winona, MN
09/25 – 09/27
$856/nighttotal: $1712 (2 )

Walkable Retreat In A Historic Neighborhood

1 4
apartment , Winona
This 4-bedroom, 3-bathroom rental is located in a historic Winona neighborhood, just moments from downtown Winona.
This rental sleeps 12 guests and features a private swimming pool, air conditioning, internet, parking, and a kitchen, offering a peaceful retreat with modern comforts.
Studio King With Kitchenette-44° North - Winona, MN
Winona, MN
10/02 – 10/14
$326/nighttotal: $3912 (12 )

Studio King With Kitchenette-44° North

1 2
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

Charming Home: 3 Blocks To Winona State University - Winona, MN
9.7 3 reviews
Winona, MN
10/02 – 10/14
$287/nighttotal: $3444 (12 )

Charming Home: 3 Blocks To Winona State University

3 2
house , Winona
This charming house is located just three blocks from Winona State University, a short distance from downtown Winona and a 30-minute drive from La Crosse. The quiet neighborhood offers a peaceful setting close to the city center.
The house has three bedrooms, two bathrooms, and a floor area of 1690 square feet, comfortably accommodating up to nine guests. The house comes with modern amenities like a fully equipped kitchen, a fireplace, a flat-screen TV, and free WiFi.
The Exchange 14 | Historic Bldg, Studio, Dwntwn - Winona, MN
10 12 reviews
Winona, MN
10/02 – 10/14
$241/nighttotal: $2892 (12 )

The Exchange 14 | Historic Bldg, Studio, Dwntwn

1 2
studio , Winona
This studio apartment is situated in Winona's historic district, just a short walk from the Mississippi River, Winona State University, and local attractions like the Winona County Historical Society and the Minnesota Marine Art Museum. The studio features a fully equipped kitchen with a refrigerator, microwave, and dishwasher, as well as a washer and dryer, making it ideal for short-term stays for up to two guests.
~ Third Street Suites ~ #9 - Winona, MN
9.9 582 reviews
Winona, MN
10/02 – 10/14
$129/nighttotal: $1548 (12 )

~ Third Street Suites ~ #9

1 2
apartment , Winona
This one-bedroom apartment is in downtown Winona, just steps from the Mississippi River, Lake Winona, and Winona State University, making it a perfect base for exploring the city. Guests rave about the apartment's excellent location, cleanliness, and overall experience.
The apartment comfortably sleeps two guests and offers a fully equipped kitchen, a spacious living room with a comfortable couch and a 42-inch HD TV, and a bedroom with a queen-size bed and two walk-in closets. Enjoy amenities like fast Wi-Fi, laundry facilities, reserved parking in the winter, and natural light from two skylights.
Unbeatable Location! Large Deck & Firetable! - Winona, MN
10 6 reviews
Winona, MN
09/25 – 09/27
$574/nighttotal: $1148 (2 )

Unbeatable Location! Large Deck & Firetable!

2 4
apartment , Winona
This newly renovated 2-bedroom, 2-bathroom apartment is located downtown Winona, steps from the Mississippi Riverfront, dining, bars, and cultural attractions, offering a blend of historic character and modern comfort in a boutique-hotel experience.
This apartment features soaring ceilings, exposed brick, vintage decor, a furnished deck with a fire table (seasonal), an on-site workout area, in-unit laundry, and free parking for up to 5 guests, with exceptional walkability to local coffee shops, restaurants, boutiques, and live music venues.
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