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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, (58)
"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, (89)
"Very clean accommodations. Very secluded location. Private, peaceful, and quiet. Very relaxing environment. We found it to be a very good central location for going out and exploring the trails."
Secluded Ozarks Tiny House cabin in Eminence, MO

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.

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!!

#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 CA $359
CA $532 total
includes taxes & fees
Dec 26 - Dec 27
#ContemplationCabin on the Jacks Fork River!

Secluded Ozarks Bunk House Cabin at Old Desperado Ranch

10.0 out of 10, Exceptional, (45)
"It was quite and relaxing. We really enjoyed it. "
Secluded Ozarks Bunk House Cabin at Old Desperado Ranch

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, (125)
"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!"
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

Private Hilltop Cabin Near Current River

10.0 out of 10, Exceptional, (52)
"It was great"
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, (17)
"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 !

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 CA $228
CA $385 total
includes taxes & fees
Jan 1 - Jan 2, 2025
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, (38)
"Nice place. Would stay again."
RIVER FRONT HOUSE

Deadwood Acres cabin #1

9.8 out of 10, Exceptional, (40)
"Everything was clean and just as advertised. Ron was responsive and extremely nice. Love the area and would go back again and stay here."
Deadwood Acres cabin #1

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 CA $164
CA $316 total
includes taxes & fees
Jan 22 - Jan 23, 2025
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, (95)
"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!"
Unique cabins in the woods<br>Not friendly for Street Bikes. Beautifulin FALL!

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

9.6 out of 10, Exceptional, (13)
"This is a nice cabin in the woods. It's quiet, comfortable, and clean. There was nothing I didn't like. "
Pine Perfect Cabin on the edge of town only 1/2 mile from Current River!

2 Bedroom Home less than 2 miles to Jacks Fork River

10.0 out of 10, Exceptional, (18)
"Thank you for sharing your beautiful home! Everything about it was perfect. We loved the fur mattresses and the quiet secluded yard. Everything was so clean. Everything we needed was there. Thank you;we would highly recommend!"
2 Bedroom Home less than 2 miles to Jacks Fork River
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, (58)
"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!

Echo Bluff State Park

2.5 star property
9.6 out of 10, Exceptional, (175)
"Have stayed at this Lodge before, staff is always pleasant and lodging is clean and up to date."
The price is CA $149
CA $158 total
includes taxes & fees
Dec 31 - Jan 1, 2025
Echo Bluff State Park

Honeysuckle Inn - Mountain View

3.0 star property
8.6 out of 10, Excellent, (255)
"Very clean and comfortable. Great beds. Breakfast was cold/hot cereal, toast, and yogurt."
The price is CA $158
CA $171 total
includes taxes & fees
Dec 26 - Dec 27
Honeysuckle Inn - Mountain View
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.

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 can relax into your vacation with a selection of games and a spa 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 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.