Photo by Jessica Richter

Winona Holiday Rentals

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Holiday Rentals in Winona

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

10.0 out of 10, Exceptional, (57)
"Exactly as liste very nice accommodations and centrally located for lots of outdoor activities thanks George for your hospitality "
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

Secluded Ozarks Tiny House cabin in Eminence, MO

9.6 out of 10, Exceptional, (88)
"We loved the scenery. Traveling up the mountain road and all the way down to the current river. Absolutely loved the craftsmanship of the cabin. It was beautiful. Owners were accessible if needed and gave great suggestions on places to visit."
Secluded Ozarks Tiny House cabin in Eminence, MO

Deadwood Acres cabin #1

9.8 out of 10, Exceptional, (40)
"Relaxing on the porch or inside the cabin we were comfortable. No noise other than nature. "
Deadwood Acres cabin #1

#ContemplationCabin on the Jacks Fork River!

10.0 out of 10, Exceptional, (53)
"It was perfect for our little end of summer get away so peaceful and quite! The river is beautiful! The river is where we stayed pretty well every moment when at the cabin."
The price is AU$578
includes taxes & fees
4 Dec - 5 Dec
#ContemplationCabin on the Jacks Fork River!

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

10.0 out of 10, Exceptional, (2)
"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!"
Whole house, secluded getaway near Alley Springs, Eminence , Missouri.

Private Hilltop Cabin Near Current River

10.0 out of 10, Exceptional, (51)
"It was great"
Private Hilltop Cabin Near Current River

“ RIVER SIDE “ cabin with Private dock

9.4 out of 10, Exceptional, (32)
"Great location, great home. It was advertised with Wifi which did not work so no TV and no connectivity for our devices We had to purchase step stools as the beds were very high and our group was short. Lovely spot to visit and enjoy the Current. We would come back if we knew we had Wifi with internet "
“ RIVER SIDE “ cabin with Private dock

Secluded Eminence Ranch House Cabin in the Ozarks

9.8 out of 10, Exceptional, (90)
"Its not secluded!! the bar is right accross property, just turn around you'd see and hear it. The residents are in the same location, you will see people, horses, dogs. If you don't mind that is the spot. There's several horse stalls that house horses for events and what not. Smells of poops all day. We were out all day long so it didn't matter. Its fun if you are not there to be alone!!"
Secluded Eminence Ranch House Cabin in the Ozarks

The Cabin on Current River with Private Gravel Bar!!

8.6 out of 10, Excellent, (25)
"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 Cabin on Current River with Private Gravel Bar!!

Deadwood acres cabin #3

10.0 out of 10, Exceptional, (16)
"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! "
Deadwood acres cabin #3

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

9.8 out of 10, Exceptional, (124)
"We came to get away for a couple of days. It was so peaceful. The cabin has all you could need to prepare your meals. Shower was wonderful, good water pressure. The owners are wonderful, they responded right away to our questions. If you are looking for a quiet getaway in the country this, is it!! We would love to stay again."
Ozark seclusion with a fully loaded cozy cabin, creeks, springs ,oh my!!!

Deadwood Acres cabin #2

9.8 out of 10, Exceptional, (27)
"It was a cuite cabin. My Grandson is 6' 3" tall and it was a little small for him. It would have been nice to have some sheets for the futon. The BBQ pit was nice and a great deck.we enjoyed our stay."
Deadwood Acres cabin #2

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

9.4 out of 10, Exceptional, (15)
"Great place! Exactly as advertised. Had an issue with the upstairs A/C but it wasn’t a huge deal because the weather was nice. Only 2 minutes from town. Very convenient. I will definitely book here again on my next hunting trip. "
Kings Cabin on the edge of town only 1/2 mile from Current River !

Newly renovated early 1900’s farmhouse

10.0 out of 10, Exceptional, (14)
"This old farmhouse has been spectacularly renovated. Hearts feel right at home when you enter here. Such a wonderful place for resting, relaxing and rejuvenating the spirit. Marsha is the most amazing hostess, who creates the most picture perfect experience for guests who enter her home. If you love peace and quiet, this charmer is the perfect retreat for you. "
The price is AU$416
includes taxes & fees
4 Dec - 5 Dec
Newly renovated early 1900’s farmhouse

New cabin located on the jacks fork river front.

8.0 out of 10, Very good, (5)
"We had a wonderful stay in the cabin. It was nice and had everything that we needed. The floor was not super clean and the hideawayneed was a little dirty, but we had a great time anyway and would stay there again"
New cabin located on the jacks fork river front.

RIVER FRONT HOUSE

9.6 out of 10, Exceptional, (37)
"House was in a great location for a family stay."
RIVER FRONT HOUSE

Cozy cabin close to beautiful Current river and surrounded by a national forest!

9.0 out of 10, Wonderful, (2)
"Very nice location and cabin. Needs few repairs and will be the perfect get away!!!"
Cozy cabin close to beautiful Current river and surrounded by a national forest!

Chasen Summer! 1/2 Mile from Current River!

9.4 out of 10, Exceptional, (33)
"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....
Chasen Summer! 1/2 Mile from Current River!

Quiet 2 story Cabin on 32 acres near eleven point river

10.0 out of 10, Exceptional, (12)
"We were looking for a secluded getaway and we were not disappointed. We enjoyed the local hiki ng trails, with Greer Springs being our favorite. The cabin was really big and well maintained. Lots of extras were provided. We saw a lot of deer and birds but our favorite was the large skunk that made its way back and fourth during the evening in the meadow across the back fence line. We would stay here again."
The price is AU$339
includes taxes & fees
3 Dec - 4 Dec
Quiet 2 story Cabin on 32 acres near eleven point river

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

10.0 out of 10, Exceptional, (94)
"Tucked away in natures beauty."
Unique cabins in the woods<br>Not friendly for Street Bikes. Beautifulin FALL!
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.
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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, (57)
"Exactly as liste very nice accommodations and centrally located for lots of outdoor activities thanks George for your hospitality "
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, (249)
"Quaint, clean, comfortable Inn. Very inviting, something out of a hallmark movie. ❤️"
The price is AU$148
includes taxes & fees
5 Dec - 6 Dec
Honeysuckle Inn - Mountain View

Current River Inn

3.0 star property
8.2 out of 10, Very good, (130)
"Older hotel but you can tell the management has tried to keep things in good shape. Staff was great!!! Place was quiet and comfortable! "
The price is AU$140
includes taxes & fees
3 Dec - 4 Dec
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.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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.