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Winona Vacation Rentals

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Vacation Rentals in Winona

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
10.0 out of 10, Exceptional, (47)
"Checking in was so easy. The property was comfy and everyone had their own space if needed but there was also space to have all hang out. It was a bit rainy when we stayed, but with the garage space with game it kept the teen happy. They played ping pong, darts and corn hole. We did get to fish and swim on the Jack's Fork river. Plus vist Alley Springs old mill which had a interesting history. We would definitely stay again when coming to this area."
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
Cozy on Current River
10.0 out of 10, Exceptional, (4)
"Would stay again."
Cozy on Current River
Secluded Ozarks Tiny House cabin in Eminence, MO
9.8 out of 10, Exceptional, (81)
"We loved the Tiny House...the area is so beautiful"
Secluded Ozarks Tiny House cabin in Eminence, MO
Van Buren Home Near The Landing- with Arcade & 3 Bedrooms
10.0 out of 10, Exceptional, (4)
"Was really close to current river comfortable and affordable place to stay."
The price is CA $197
CA $320 total
includes taxes & fees
Jul 11 - Jul 12
Van Buren Home Near The Landing- with Arcade & 3 Bedrooms
RIVER FRONT HOUSE
9.6 out of 10, Exceptional, (25)
"Rental was clean inside, but the deck area needs attention. There was a thick layer of pollen on all the furniture, and a dead bird in the center of the floor. It was filthy. It appeared as if the deck hadn't had attention or cleaning for a long time. It definitely was not prepared fir the rental."
RIVER FRONT HOUSE
Secluded Ozarks Bunk House Cabin at Old Desperado Ranch
10.0 out of 10, Exceptional, (38)
"This was a mom and son trip. My friend and I took our two teenage boys…. To say that it was such an enjoyable experience would be a complete understatement…. This is a slice of heaven on earth!"
Secluded Ozarks Bunk House Cabin at Old Desperado Ranch
Family-friendly Cabin w/150 ft Current River frontage in Ozark Scenic River
9.6 out of 10, Exceptional, (50)
"It was a great cabin! We all enjoyed it very much! The hill to the water was brutal. I would recommend fixing that for clients or be more up front about it. It is dangerous unless you are about 11-35! The location was great and very easy to get to and close to town."
Family-friendly Cabin w/150 ft Current River frontage in Ozark Scenic River
Ozark seclusion with a fully loaded cozy cabin, creeks, springs ,oh my!!!
9.8 out of 10, Exceptional, (107)
"An absolutely wonderful experience! If you're looking for a cabin in a private secluded area that is completely safe I highly recommend the Birch Tree Cabin. It's less then 10 minutes from downtown Eminence and located in Ozark National Scenic Riverways. The Cabin is clean and nicely furnished and the host was extremely friendly and was available whenever we reached out. I will definitely stay with them any time I'm in the area..."
Ozark seclusion with a fully loaded cozy cabin, creeks, springs ,oh my!!!
Pine Perfect Cabin on the edge of town only 1/2 mile from Current River!
9.8 out of 10, Exceptional, (6)
"Nice quiet location thats feels like the country but is still close to town an necessities."
Pine Perfect Cabin on the edge of town only 1/2 mile from Current River!
Relax on beautiful Current River in Luxury!
10.0 out of 10, Exceptional, (6)
"Everything was perfect. The host did a really good job. Sending me an itinerary and telling me about everything around me. Just had a great time and would definitely staying there again."
Relax on beautiful Current River in Luxury!
Deadwood Acres cabin #2
9.8 out of 10, Exceptional, (19)
"This place was awesome and our host was the best"
Deadwood Acres cabin #2
Ozark Oasis 3 B/ 3 B in Eminence with Spectacular View!
9.8 out of 10, Exceptional, (24)
"This was our second time staying at this location. It never disappoints and the host is amazing to work with."
Ozark Oasis 3 B/ 3 B in Eminence with Spectacular View!
Private Hilltop Cabin Near Current River
10.0 out of 10, Exceptional, (38)
"Loved the house, very clean and spacious. We all had a great time and ready for another run. Thanks so much for sharing this property with all us river people. Sincerely, The Hays family"
Private Hilltop Cabin Near Current River
Kings Cabin on the edge of town only 1/2 mile from Current River !
9.4 out of 10, Exceptional, (14)
"Everything went well."
Kings Cabin on the edge of town only 1/2 mile from Current River !
Deadwood acres cabin #3
10.0 out of 10, Exceptional, (8)
"We were greatly surprised how cute ot was. We stayed to go kayaking."
Deadwood acres cabin #3
Deadwood Acres cabin #1
9.8 out of 10, Exceptional, (33)
"Peaceful, quiet, and simple. Loved the outdoor space and the mostly secluded area. Would have appreciated directions other than google map. Google...YIKES!"
Deadwood Acres cabin #1
The Cabin on Current River with Private Gravel Bar!!
9.0 out of 10, Wonderful, (19)
"Cabin appeared to be an older updated River Cabin, but had newer Appliances, furniture, fixtures and paint. The moth ball smell was 'overwhelming' until we aired it out. It overlooks the river, with a beautiful view. Unless you plan a little hike, you'll want to drive down to the river and fire pit. Might be a little challenging for a small vehicle. Our stay was to kayak, parked a truck at the cabin landing and had no problems. Would deffinatley recommend, plenty of room and totally enjoyed or...
The Cabin on Current River with Private Gravel Bar!!
Country and lovin’ it @ Robin’s Nest Cabin @ Current River/Jacks Fork River
9.8 out of 10, Exceptional, (6)
"Great location for a getaway."
Country and lovin’ it @ Robin’s Nest Cabin @ Current River/Jacks Fork River
Beautiful Scenic River Cabin just 1/2 mile from Current River!
9.2 out of 10, Wonderful, (5)
"The lack of variety of pots and pans were a bummer. Plus, the ones that were there were dirty. Consequently, we had to change our plans about cooking in the room, except in the microwave. Only 4 place settings of flatware, even though the cabin has sleeping for 8. However, watching the eclipse from the parking lot was spectacular! Didn’t have to drive anywhere to see it so we didn’t have to fight any traffic. That, in itself, made up for any inconveniences in the room itself. The area is...
Beautiful Scenic River Cabin just 1/2 mile from Current River!
#ContemplationCabin on the Jacks Fork River!
10.0 out of 10, Exceptional, (48)
"While the weather was less than cooperative the sound of the river and birds singing, while enjoying a cup of coffee sitting on the front porch was exactly what the Dr ordered! Hopefully we’ll get to return again someday"
#ContemplationCabin on the Jacks Fork River!
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See all available properties in Winona
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.

Winona Vacation Rental Travel Info

Other types of properties in Winona you may be interested in

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
10.0 out of 10, Exceptional, (47)
"Checking in was so easy. The property was comfy and everyone had their own space if needed but there was also space to have all hang out. It was a bit rainy when we stayed, but with the garage space with game it kept the teen happy. They played ping pong, darts and corn hole. We did get to fish and swim on the Jack's Fork river. Plus vist Alley Springs old mill which had a interesting history. We would definitely stay again when coming to this area."
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!
Honeysuckle Inn - Mountain View
3.0 star property
8.6 out of 10, Excellent, (200)
"Everything about this property was especially delightful except the mattress. It appeared new but felt like a box spring so if you like a firm mattress you will enjoy the room we had. "
The price is CA $152
CA $164 total
includes taxes & fees
Jun 29 - Jun 30
Honeysuckle Inn - Mountain View
Current River Inn
3.0 star property
8.0 out of 10, Very good, (109)
"Good location. Close to river and stores and we loved the pool and decently priced. Would definitely come back."
The price is CA $116
CA $125 total
includes taxes & fees
Jul 8 - Jul 9
Current River Inn
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winona. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Winona?

Yes, we give you a choice of vacation rentals near the most popular attractions in Winona, or you can select a more remote option if you're looking for a relaxing stay.

What's the top vacation rental in Winona?

Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!: Visitors give good reviews to this Winona vacation home rental, which is located on a river and has a patio, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 vacation rental in Winona like?

Vacation rentals are private properties you can stay in for short or long periods in Winona. Vacation rentals feature extras such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for families.

Recent reviews of Winona properties
Expedia verified reviews