Discover a selection of 49 vacation rentals in Winona that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and fireplaces. Prices start at $113 per night, and houses and cabins are popular options for a stay in Winona. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Winona
Destination guide

Travel to beautiful Winona

The area's museums and churches are just a few of the reasons to vacation in Winona. Travelers to this scenic city praise the bird watching, wildlife and gardens. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.


Sightseeing in and around Winona

Do you want to find things to do while you're in the area? Venture out of your vacation home and check out everything that makes Winona a one-of-a-kind vacation spot. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Cedar Valley Golf Course (5.9 mi / 9.5 km)
  • Elmaro Vineyard (8.1 mi / 13 km)
  • Trempealeau Moutain Golf Club (10.7 mi / 17.2 km)
  • Riverside Amusement Park (21.9 mi / 35.2 km)
Natural features

Exploring the natural landscape of Winona

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Winona is a great place to get outside. Here are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city center:

  • Sugar Loaf (2.9 mi / 4.6 km)
  • Garvin Heights City Park (3 mi / 4.8 km)
  • Lake Lodge Recreation Center (3.7 mi / 5.9 km)
  • Aghaming Park And Preserve (5 mi / 8 km)
  • Trempealeau Mountain (7.6 mi / 12.3 km)
  • Perrot State Park (8.7 mi / 14 km)
How to get there

Traveling to and around Winona

The nearest airport is in La Crosse, WI (LSE-La Crosse Municipal), located 20.4 mi (32.8 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Rochester, MN (RST-Rochester Intl.), which is 42.5 mi (68.4 km) away.

If you prefer train travel, the main station serving the city is Winona Station.

How many vacation rentals are available around Winona?

Our 2021 property listings offer a large selection of 49 vacation rentals around Winona. From 39 house rentals to 9 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.