Photo by Jessica Richter

Winona Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Winona

“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.
10.0 out of 10, Exceptional, (13)
"This property is beautiful. It had everything we needed to enjoy our stay. I would highly recommend this cabin. So cute."
“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
10.0 out of 10, Exceptional, (73)
"Just as always expected. Couldn’t ask for anything more! Great place. Great hosts. "
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
Springside Cottage in beautiful Eminence. Great outdoor space - NEW Hot tub!
9.8 out of 10, Exceptional, (12)
"My family (kids 17, 16, and 7 years old plus husband and I) stayed at Springside Cottage Monday through Friday and had a wonderful little vacation. The location is perfect and the cottage was very comfortable. The host was super responsive and kind. Would stay again!"
Springside Cottage in beautiful Eminence. Great outdoor space - NEW Hot tub!
Collier Cabin in Pine Hollow ~ Eminence, MO
9.8 out of 10, Exceptional, (20)
"Best host’s around and a very private peaceful cabin. Everything about this place is great. Second time staying there and I will definitely be back!"
Collier Cabin in Pine Hollow ~ Eminence, MO
Unbeatable convenience in amazing Eminence!
10.0 out of 10, Exceptional, (17)
"Everything was very nice and cozy and also convenient."
Unbeatable convenience in amazing Eminence!
Kings Cabin on the edge of town only 1/2 mile from Current River !
9.4 out of 10, Exceptional, (25)
"Very nice cabin! Better than staying at a hotel, at near the same price."
Kings Cabin on the edge of town only 1/2 mile from Current River !
Fox Pen Cabins Cabin #2 Not friendly for street bikes… Pet-Friendly
3.0 star property
10.0 out of 10, Exceptional, (8)
"Great little cabin, roads to cabin not the best but worth it!"
Fox Pen Cabins Cabin #2 Not friendly for street bikes… Pet-Friendly
Beautiful, secluded cabin in the hills of the Ozarks.
9.8 out of 10, Exceptional, (136)
"Lovely cabin in a peaceful pasture. If you’re looking for quiet solitude with comfort. This is a place you’ll love "
Beautiful, secluded cabin in the hills of the Ozarks.
Lazy River Cabin on the edge of town only 1/2 mile from Current River !
8.8 out of 10, Excellent, (14)
"Love Current River! Love this location to stay!!"
Lazy River Cabin on the edge of town only 1/2 mile from Current River !
Quiet 2 story Cabin on 32 acres near eleven point river
10.0 out of 10, Exceptional, (15)
"Had a great time. Really nice place, great to have WiFi. If you have AT&T the WiFi in area is not the greatest. You will have if At the house. Enjoyed visiting, hiking Mark Twain National Forest. The host was so kind and helpful. Family enjoyed the little getaway. "
The price is AU$331
includes taxes & fees
19 Oct - 20 Oct
Quiet 2 story Cabin on 32 acres near eleven point river
Cabin in the heart of the Ozark National Scenic Riverway!
10.0 out of 10, Exceptional, (56)
"All of my friends love staying here for our annual float trip. The cabin is decorated beautifully and the porch is our favorite spot to visit with each other. It’s the perfect place to create lasting memories. "
Cabin in the heart of the Ozark National Scenic Riverway!
Deadwood Acres cabin #1
9.8 out of 10, Exceptional, (52)
"Out groups of 7 had a wonderful time in cabins 1&2. Perfect location, wooded & secluded area but still close to town. Thanks for a great stay in Eminence!"
Deadwood Acres cabin #1
Triple H Properties
8.6 out of 10, Excellent, (27)
"Worked out great for friends to stay for a float trip weekend. "
Triple H Properties
Deadwood Acres cabin #2
9.8 out of 10, Exceptional, (36)
"This place is a hidden gem we will def be back!"
Deadwood Acres cabin #2
Secluded Ozarks Bunk House Cabin at Old Desperado Ranch
10.0 out of 10, Exceptional, (54)
"Great place for a couple to have a little getaway! It is small, but clean, and the owners are super friendly! "
Secluded Ozarks Bunk House Cabin at Old Desperado Ranch
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
10.0 out of 10, Exceptional, (32)
"Beautiful property, I’d recommend to anyone going here to stay here."
The price is AU$210
includes taxes & fees
12 Nov - 13 Nov
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Charming Bunk House Suite in Eminence with AC/Heat, Kitchenette & full bath
9.6 out of 10, Exceptional, (5)
"This little place was so cute and relaxing, it was very quiet, close to the kayaking place that we used which was windys. We will definitely be back, thank you for alowing us to enjoy your place. "
Charming Bunk House Suite in Eminence with AC/Heat, Kitchenette & full bath
2 Bedroom Home less than 2 miles to Jacks Fork River
9.8 out of 10, Exceptional, (26)
"Check in was easy and the house was clean!"
2 Bedroom Home less than 2 miles to Jacks Fork River
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
9.4 out of 10, Exceptional, (15)
"Decent place, lots of ladybugs in the house!"
The price is AU$342
includes taxes & fees
24 Oct - 25 Oct
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Charming 2-bedroom house with AC, WiFi in serene Van Buren
2.0 star property
9.0 out of 10, Wonderful, (15)
"It was beautiful and homey. We really enjoyed our stay. "
The price is AU$261
includes taxes & fees
22 Oct - 23 Oct
Charming 2-bedroom house with AC, WiFi in serene Van Buren
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Winona Hotel Reviews

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as AU$210 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winona has to offer?

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!: This highly rated holiday home rental in Winona is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

What’s there to see and do in Winona?

Rocky Falls and Mark Twain National Forest are a couple of lovely local spots to get outside and enjoy nature. While here, Ozark National Scenic Riverways and Current River are other places worth a visit.

What’s a holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.