A river surrounded by dense green forest.

Winona Vacation Rentals

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Our top choices for Winona vacation rentals

1. Newly renovated early 1900’s farmhouse

Newly renovated early 1900’s farmhouse
Birch Tree
10.0 out of 10, Exceptional, (28 reviews)
"One of the best places I have ever stayed! Marsha was a wonderful host! "
United States
Devon J.
The price is CA $236
CA $413 total
includes taxes & fees
Sep 3 - Sep 4
Newly renovated early 1900’s farmhouse

2. Bungalow with Hot Tub in Birch Tree

Bungalow with Hot Tub in Birch Tree
Birch Tree
10.0 out of 10, Exceptional, (5 reviews)
The price is CA $236
CA $397 total
includes taxes & fees
Sep 1 - Sep 2
Bungalow with Hot Tub in Birch Tree

3. Hogan's Hideout Cozy Cottage #5

Hogan's Hideout Cozy Cottage #5
Eminence
9.6 out of 10, Exceptional, (8 reviews)
"The cabin was clean and had everything we needed. We did not spend a lot of time there during the day but it was just what we needed, especially with the heat! The A/C unit worked great. "
United States
Shawna C.
The price is CA $202
CA $295 total
includes taxes & fees
Sep 1 - Sep 2
Hogan's Hideout Cozy Cottage #5

4. New cabin located on the jacks fork river front.

New cabin located on the jacks fork river front.
Eminence
8.8 out of 10, Excellent, (15 reviews)
"Great location"
United States
Trent B.
The price is CA $348
CA $474 total
includes taxes & fees
Sep 7 - Sep 8
New cabin located on the jacks fork river front.

5. Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride
Eminence
9.6 out of 10, Exceptional, (27 reviews)
"Nice little place. Great amenities. Great host. Perfect for a weekend getaway to kayak and hike."
United States
Kent L.
The price is CA $213
CA $317 total
includes taxes & fees
Sep 1 - Sep 2
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

6. The Western

The Western
Eminence
9.6 out of 10, Exceptional, (7 reviews)
"Cute decor, comfortable beds, covered patio with grill and clean hot tub!"
United States
Robert
The price is CA $167
CA $210 total
includes taxes & fees
Sep 6 - Sep 7
The Western

7. Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12

Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
Van Buren
10.0 out of 10, Exceptional, (17 reviews)
"Amazing place for our crew of 7 adults and 6 kids to stay. Everything was clean and perfectly located for exploring current river."
United States
Dillion
The price is CA $438
CA $813 total
includes taxes & fees
Sep 1 - Sep 2
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12

8. Peaceful Stay Near Current River

Peaceful Stay Near Current River
Van Buren
10.0 out of 10, Exceptional, (4 reviews)
"We had a great stay at this house! Super clean, and easy find! Will definitely stay here again!"
United States
Danni H.
The price is CA $452
CA $722 total
includes taxes & fees
Sep 1 - Sep 2
Peaceful Stay Near Current River

9. White Family Suite

White Family Suite
Eminence
The price is CA $382
CA $639 total
includes taxes & fees
Sep 10 - Sep 11
White Family Suite

10. Cozy Corner

Cozy Corner
Van Buren
9.8 out of 10, Exceptional, (8 reviews)
"Host was amazing and extremely responsive!! Close to everything we wanted to do"
United States
Dierdre
The price is CA $207
CA $330 total
includes taxes & fees
Sep 4 - Sep 5
Cozy Corner

11. #ContemplationCabin on the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!
Summersville
10.0 out of 10, Exceptional, (84 reviews)
"Cabin was clean and cosy. Took a little bit of patience to get the fire going but it warmed up the cabin quite nicely once going."
United States
Teagan B.
The price is CA $348
CA $498 total
includes taxes & fees
Sep 7 - Sep 8
#ContemplationCabin on the Jacks Fork River!

12. Hogan's Hideout Cottage #8

Hogan's Hideout Cottage #8
Eminence
8.0 out of 10, Very good, (4 reviews)
"Nice private and rustic"
United States
Anonymous traveller
The price is CA $202
CA $305 total
includes taxes & fees
Sep 1 - Sep 2
Hogan's Hideout Cottage #8

13. Hogan's Hideout Cottage #7

Hogan's Hideout Cottage #7
Eminence
8.6 out of 10, Excellent, (14 reviews)
"Very helpful with anything we needed!"
United States
Janice
The price is CA $202
CA $305 total
includes taxes & fees
Sep 1 - Sep 2
Hogan's Hideout Cottage #7

14. Easy Street Apartment

Easy Street Apartment
Van Buren
10.0 out of 10, Exceptional, (3 reviews)
"The property was clean and comfortable. It had everything we needed for a weekend stay innVan Buren."
United States
Tara W.
The price is CA $207
CA $329 total
includes taxes & fees
Sep 1 - Sep 2
Easy Street Apartment

15. Home Near Eleven Point River & Nat'l Forest!

Home Near Eleven Point River & Nat'l Forest!
3.0 star property
Alton
The price is CA $161
CA $286 total
includes taxes & fees
Sep 4 - Sep 5
Home Near Eleven Point River & Nat'l Forest!

16. Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!
Van Buren
9.0 out of 10, Wonderful, (10 reviews)
"Perfect spot to get away with the family!"
United States
Jennifer P.
The price is CA $219
CA $347 total
includes taxes & fees
Sep 1 - Sep 2
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

17. Quiet 2 story Cabin on 32 acres near eleven point river

Quiet 2 story Cabin on 32 acres near eleven point river
Alton
10.0 out of 10, Exceptional, (23 reviews)
"This was one of the best trips we’ve ever had! The cabin was beautiful and stocked with so many nice surprises. We loved our stay!"
United States
Lisa B.
The price is CA $159
CA $314 total
includes taxes & fees
Sep 1 - Sep 2
Quiet 2 story Cabin on 32 acres near eleven point river

18. Nice 2-bedroom cottage with AC in Mountain View

Nice 2-bedroom cottage with AC in Mountain View
Mountain View
10.0 out of 10, Exceptional, (3 reviews)
"What a great, off the beaten path and away from people noise cabin. Wonderful views and very relaxing! Clean, new and comfortable. Will be back!"
United States
Deena P.
The price is CA $193
CA $232 total
includes taxes & fees
Sep 1 - Sep 2
Nice 2-bedroom cottage with AC in Mountain View

19. Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Clearwater Lake, cabin minutes from Bluff View Marina & boat dock
Piedmont
10.0 out of 10, Exceptional, (45 reviews)
"Would stay here again"
United States
Steve A.
The price is CA $167
CA $204 total
includes taxes & fees
Sep 1 - Sep 2
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

20. Home Near Eleven Point River & Nat'l Forest!

Home Near Eleven Point River & Nat'l Forest!
Alton
7.0 out of 10, Good, (2 reviews)
"We had a great stay! The getaway was clean and inviting. Its super artsy and creative-just a really fun place. Amber and Marc were very informative. Any and all questions we had were answered. Everything was ready and available. Amber is super helpful and just a really great person. Will be back and highly recommend!!!"
United States
Amy
The price is CA $110
CA $286 total
includes taxes & fees
Sep 4 - Sep 5
Home Near Eleven Point River & Nat'l Forest!
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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Top Winona Hotel Reviews

Find out more about Winona

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

What’s there to see and do in Winona?

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