Winona Holiday Rentals from €360: Search Short-Term Rentals

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Holiday Rentals in Winona

"We chose this property for our 1st Christmas away from home. I traveled with my husband, 3 kids aged 10-17, and 2 dogs. Walking in the first thing we saw was the beautiful Christmas tree and the decorated screened in porch. The home was very clean and had everything we could possibly need. The furniture was comfy and there were plenty of places for everyone to sit and relax. The bedrooms were spacious. The closets provided more than enough space to hang the clothes we brought with us. These...

"The owners were very friendly and quick to respond to any questions. We came down for our annual sxs ride The weather was getting bad and they even offered a stay on them for another night if needed. The cabin- very spacious and perfect for any group size. Clean and adorable with all the furnishings. The view doesn’t get any better. We would definitely stay there again!! "

"The property is terrific -- we loved the river access -- and the hosts do a great job providing all the various amenities and tools to help make your stay fun and easy. Really nice hosts with great communication."

includes taxes & fees

23 Feb - 24 Feb

"This is a nice cabin in the woods. It's quiet, comfortable, and clean. There was nothing I didn't like. "

"Nice place. Would stay again."

"This location was a perfect place for a large family gathering. There was adequate space for a couple of families to stay overnight! Close to Harvey’s canoe/raft rentals! The host was very helpful!"

"Property location is excellent! The down side is there are 28 steps to access the cabin. We had a couple of young children that made the steps a little challenging and worrisome.for safety issues. There was no propane but we bought some in order to grill. Grill works but is hard to control heat settings. Other than that, it was a wonderful, relaxing stay. Beautiful property with a beautiful view! Would stay there again."

"We stayed here just to get away for the weekend. We were blown away with how much we loved it. We were greeted by “Carl” the cat. Our stay was very quiet but full of sights. The horses are so fun to just sit and watch. We also had all 3 guard dogs come join us for dinner one night lol. Our cabin was clean, cozy, and had everything we needed! We are definitely going to be coming back! "

"The cabin was secluded but with help not too far away since the owners live on the property up the hill. The cabin is cute as a button seemed to have just about everything you would need to stay other than food and your personal things. Look forward to coming back."

"House is really lovely and comfortable, we (7 adults) had a wonderful stay. The view of the river is beautiful and the most intrepid in our group went down to the river's edge and said it was even more gorgeous down there."

"We have stayed many places in Van Buren and this one tops them all. Beautiful views of the ozark mountains from the hilltop view of this houses location. Close to town with the convenience of multiple restaurants and grocery stores. The house was extremely clean and well prepped with all of the necessities. We will definitely be booking this again in the summer whenever we can. I recommend checking out HJ Redbeards for lunch or dinner, great food including some awesome seafood options. Thanks...

"Property is prime location for floating the jacks fork and current river. Very spacious! Fits the need for a cool place to stay and cook "

"We had 3 cozy generations stay at Ron’s beautiful cabin for the weekend. We enjoyed the space and surroundings. The layout is wonderful for multiple people and there is room to explore the property for short hikes. We grilled, cooked, and roasted marshmallows over the fire! We also got to check out Ally Springs, which was amazing. Definitely recommend! "

"Very quiet and quant little cabin. Nice walk to the creek. Close to everything. Would stay there again "

"Our stay was fantastic! We were looking for secluded and this was perfect! 20 minutes from the nearest town. Cabin was fully stocked and then some. Owners were very responsive to any needs and left great directions, yet GPS still worked just fine for us. We most definitely plan on going back!"

"It was a great surprise to find this cabin in the woods close to family. It checked all the boxes with a clean, comfortable space with internet, hot water, and peace and quiet. Lots of nice thoughtful touches throughout. Don't be deterred by the "rough roads" comments. Really enjoyed our stay and hope to be back!"

"It was quite and relaxing. We really enjoyed it. "

"Fantastic property and the gravel bar was amazing to relax on. Interior was nice and perfect size for a family with up to 4 kids, the bunk beds are easily full size mattresses! Amenities were nice and sheets and towels definitely clean. The back deck is amazing for morning coffee or peaceful evening and having the smart TVs made for great evening activities since we brought our switch. 10/10 would definitely stay here again!"

"Due to a situation beyond the property owners control we weren’t able to stay at the original cabin but they acted quickly and moved us to another. Great service and we had a great time. "

"The house was clean, cozy, stocked very well of all items including kitchen items, & host provided so many extra items that helped make our stay wonderful. Was so thankful that the host & the house was pet friendly. Great inside & outside area for all family members including pet family. Host was quick to respond & provided detailed information. Host was very kind & helped me with all items. We will stay here again & I will share all the fabulous information about the host, house, & location....

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Other types of properties in Winona you may be interested in

"We chose this property for our 1st Christmas away from home. I traveled with my husband, 3 kids aged 10-17, and 2 dogs. Walking in the first thing we saw was the beautiful Christmas tree and the decorated screened in porch. The home was very clean and had everything we could possibly need. The furniture was comfy and there were plenty of places for everyone to sit and relax. The bedrooms were spacious. The closets provided more than enough space to hang the clothes we brought with us. These...

"This is such a beautiful place to visit. We love going to Shannon County and staying at Echo Bluff. "

includes taxes & fees

6 Mar - 7 Mar

"One of the best along highway 60 in MO"

includes taxes & fees

20 Feb - 21 Feb

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, apart-hotels, 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 favorite 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 depends 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 €360 per night. Entering your travel dates in the search wizard you might find 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.

Recent reviews of Winona properties

5/5 Excellent

"This is such a beautiful place to visit. We love going to Shannon County and staying at Echo Bluff. "

A verified traveller stayed at Echo Bluff State Park

Posted 2 weeks ago

Secluded Ozarks Tiny House cabin in Eminence, MO

5/5 Excellent

Hard To Leave!

"We stayed here just to get away for the weekend. We were blown away with how much we loved it. We were greeted by “Carl” the cat. Our stay was very quiet but full of sights. The horses are so fun to just sit and watch. We also had all 3 guard dogs come join us for dinner one night lol. Our cabin was clean, cozy, and had everything we needed! We are definitely going to be coming back! "

A verified traveller stayed at Secluded Ozarks Tiny House cabin in Eminence, MO

Posted 3 weeks ago

#ContemplationCabin on the Jacks Fork River!

5/5 Excellent

Beautiful, quiet, will be back

"The property is terrific -- we loved the river access -- and the hosts do a great job providing all the various amenities and tools to help make your stay fun and easy. Really nice hosts with great communication."

A verified traveller stayed at #ContemplationCabin on the Jacks Fork River!

Posted 2 months ago

Ozark Oasis 3 B/ 3 B in Eminence with Spectacular View!

5/5 Excellent

Amazing property

"The owners were very friendly and quick to respond to any questions. We came down for our annual sxs ride The weather was getting bad and they even offered a stay on them for another night if needed. The cabin- very spacious and perfect for any group size. Clean and adorable with all the furnishings. The view doesn’t get any better. We would definitely stay there again!! "

A verified traveller stayed at Ozark Oasis 3 B/ 3 B in Eminence with Spectacular View!

Posted 2 months ago

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

5/5 Excellent

Relaxing FamilyGetaway

"We chose this property for our 1st Christmas away from home. I traveled with my husband, 3 kids aged 10-17, and 2 dogs. Walking in the first thing we saw was the beautiful Christmas tree and the decorated screened in porch. The home was very clean and had everything we could possibly need. The furniture was comfy and there were plenty of places for everyone to sit and relax. The bedrooms were spacious. The closets provided more than enough space to hang the clothes we brought with us. These were some of the most comfy beds I have ever laid in. I can honestly say I've never slept better. In the master bath, there is both a jacuzzi bathtub and a standing shower. The tub was a walk in tub with a seat. It felt amazing to get in and soak after such a long day on the road. If I'm not mistaken, the water was from a spring fed well and it was crystal clear. In the living room, there is a cabinet filled with playing cards and other games, which we did take advantage of for a family game night. There were also tons of brochures and maps available that we were able to use to plan our ventures out and about. The outside barn with games and darts was also a plus since it rained our entire trip. The grounds were beautiful and secluded and there is a nearby creek that was so nice to sit by. Oh and as a convenience, there is a Dollar General about 5 minutes from the home in case you need anything. I hope to return again in the summer to spend more time there, hopefully without the rain! "

A verified traveller stayed at Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

Posted 2 months ago

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?

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

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Holiday Rentals in Winona

Check prices for these dates

Holiday Rentals in Winona

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

Ozark Oasis 3 B/ 3 B in Eminence with Spectacular View!

#ContemplationCabin on the Jacks Fork River!

Pine Perfect Cabin on the edge of town only 1/2 mile from Current River!

RIVER FRONT HOUSE

Whole house, secluded getaway near Alley Springs, Eminence , Missouri.

Current River Cabin

Secluded Ozarks Tiny House cabin in Eminence, MO

Secluded Eminence Ranch House Cabin in the Ozarks

Family-friendly Cabin w/150 ft Current River frontage in Ozark Scenic River

Private Hilltop Cabin Near Current River

Triple H Properties

Deadwood acres cabin #3

Deadwood Acres cabin #2

Ozark seclusion with a fully loaded cozy cabin, creeks, springs ,oh my!!!

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

Secluded Ozarks Bunk House Cabin at Old Desperado Ranch

The Loft on the River with Private Gravel bar!!

The Cabin on Current River with Private Gravel Bar!!

Chasen Summer! 1/2 Mile from Current River!

Other types of properties in Winona you may be interested in

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

Echo Bluff State Park

Honeysuckle Inn - Mountain View

Find out more about Winona

Recent reviews of Winona properties

Echo Bluff State Park

Secluded Ozarks Tiny House cabin in Eminence, MO

Current River Inn

Honeysuckle Inn - Mountain View

#ContemplationCabin on the Jacks Fork River!

Ozark Oasis 3 B/ 3 B in Eminence with Spectacular View!

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

Deadwood Acres cabin #2

Pine Perfect Cabin on the edge of town only 1/2 mile from Current River!

Frequently asked questions