Winona holiday homes, Missouri: Houses & more

Scroll through and select from holiday rentals in Winona to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. At the end of the day, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Find the best place to stay - Winona

Cabin Sits in the middle of the woods with a nice deck so you can relax.

Deadwood Acres cabin #1

Sleeps 4 · 1 bedroom · 1 bathroom

Unique cabins in the woods<br>Not friendly for Street Bikes. Beautifulin FALL!

Sleeps 5 · 3 bedrooms · 1 bathroom

Find spaces that suit your style

Find properties near top attractions in Winona

Rocky Falls

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

The natural setting of Winona is ready to explore

Learn about the unique charm of Winona with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Winona

Do you want to discover attractions to see in the area? Venture out of your cosy holiday rental and check out everything that Winona has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

Big Spring (18.6 mi / 29.9 km)
Echo Bluff State Park (21.2 mi / 34.2 km)
Rocky Falls (8.4 mi / 13.6 km)
Roy L. Beck Municipal Golf Course (10.2 mi / 16.4 km)

Exploring the natural landscape of Winona

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

Ozark National Scenic Riverways (9.6 mi / 15.5 km)
Big Spring (18.6 mi / 29.9 km)
Echo Bluff State Park (21.2 mi / 34.2 km)
Rocky Falls (8.4 mi / 13.6 km)
Cave Spring Park (16 mi / 25.8 km)
Round Spring Cave (19.4 mi / 31.3 km)

Frequently asked questions

How much does it cost to rent a holiday rental in Winona?

Different factors influence how much you pay for a holiday rental in Winona, like the length of stay, season and type of property. Still, all Vrbo homes have something in common — incredible value. Just add your travel dates to find your ideal escape.

How much does it cost to rent a beach house in Winona?

When you travel and the style and size of the property will determine the cost of your beachside stay. Put in your Winona travel dates to see all your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the features and amenities you need.

What are the top attractions for families in Winona?

If you're seeking some family-friendly fun near the heart of Winona, don't miss Rocky Falls.

How old do you have to be to rent a holiday rental in Winona?

It's advisable to check with the Winona holiday home you'd like on Vrbo as the age limit differs. However, it's normally 16, 18 or 21.

How long can I rent a holiday rental in Winona for?

It's down to the Winona property. To look over a list of options offering extended stays, simply enter your travel dates and number of people into Vrbo's search page. You can enjoy having the entire place to yourself, along with home comforts like a full kitchen, air conditioning and outdoor spaces to play in. Keep an eye out for any long-term stays that offer discounted weekly or monthly prices.