Discover a selection of 34 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 kitchens and WiFi. Prices start at $117 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.
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 2020 property listings offer a large selection of 34 vacation rentals around Winona. From 22 house rentals to 6 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a rural property in Winona?

There's something undeniably charming about a countryside retreat. If you're a born-and-bred city slicker itching for a taste of the rural life, we can help you find what you're looking for. Vrbo has 10 countryside vacation rentals in this destination. Alternatively, you might like to try something a little different. Vrbo has a great range of options to choose from, including:

  • 5 water-view vacation rentals.
  • 4 shore-front vacation rentals.
  • 3 lakefront vacation rentals.

Can I rent a house in Winona?

If you're seeking a home away from home for your trip, renting an entire house is a terrific idea. You and your group will have the space you need for all your vacation activities. There are 23 options currently on Vrbo. Prices start from $50 per night. If that doesn't match your family's taste, we have a range of different rental options to select from, such as:

  • Hotel: 8 vacation homes. Prices start from $115 per night.
  • Bed & breakfast: 4 vacation homes. Prices start from $99 per night.
  • Cabin: 3 vacation homes. Prices start from $117 per night.

Can I stay in Winona in a large group?

Getaways with your favorite people can be a lot of fun, particularly when you're under the same roof in an amazing new place! If you'll be visiting with a large group, Vrbo can help out. House vacation homes are the leading option for big groups of guests, with 7 listed here. If you're hoping to travel in a larger group, the rental options that will serve you well include:

  • Searching for vacation homes that can fit 10 of you? We have 14 that will be suitable. Prices begin from just $125 per night.
  • Need somewhere for 8 people? We have 8 that will be ideal. You can get one for as little as $175 a night.
  • Hunting down rentals to suit 20 people? You'll be delighted to know we have 4 that'll be ideal. You can book one for as little as $471 a night.

So don't fret! When you travel with us you can take your aunt, your cousin and all your buddies to Winona.