Winona Vacation Rentals

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Our top choices for Winona vacation rentals

10.0 out of 10, Exceptional, (16 reviews)
"Beautiful property, lots of fun stuff to do. Wild life was really cool, and the sky at night is insane. Can’t wait to come back next year for our eleven point trip!"
United States
Anonymous traveller
The price is CA $156
CA $309 total
includes taxes & fees
Mar 2 - Mar 3
Quiet 2 story Cabin on 32 acres near eleven point river
9.0 out of 10, Wonderful, (15 reviews)
"It was beautiful and homey. We really enjoyed our stay. "
United States
Jessica
The price is CA $96
CA $231 total
includes taxes & fees
Mar 5 - Mar 6
Charming 2-bedroom house with AC, WiFi in serene Van Buren
3.0 star property
The price is CA $268
CA $482 total
includes taxes & fees
Mar 6 - Mar 7
Walk to Current River: Ozarks Adventure Home!
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful property, I’d recommend to anyone going here to stay here."
United States
tom
The price is CA $164
CA $201 total
includes taxes & fees
Mar 1 - Mar 2
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

Vacation Home in Birch Tree

Newly renovated early 1900’s farmhouse
10.0 out of 10, Exceptional, (22 reviews)
"Place was perfect for our stay. Beautiful property. "
United States
Drew W.
The price is CA $231
CA $406 total
includes taxes & fees
Mar 11 - Mar 12
Newly renovated early 1900’s farmhouse
10.0 out of 10, Exceptional, (76 reviews)
"The cabin was beautiful and perfectly maintained. Our weekend stay was relaxing and memorable — everything was clean, comfortable, and thoughtfully managed. We’re already looking forward to returning in every season!"
United States
Kathia L.
The price is CA $342
CA $493 total
includes taxes & fees
Mar 30 - Mar 31
#ContemplationCabin on the Jacks Fork River!

Cabin in Van Buren

Hilltop House #2
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful property. Would stay again."
United States
Sharon P.
The price is CA $240
CA $370 total
includes taxes & fees
Mar 5 - Mar 6
Hilltop House #2
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful stay. Good location. Very enjoyable experience."
United States
Thomas H.
The price is CA $431
CA $800 total
includes taxes & fees
Mar 12 - Mar 13
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12
The price is CA $111
CA $203 total
includes taxes & fees
Feb 28 - Mar 1
Cozy quiet country getaway just minutes from the Current River
10.0 out of 10, Exceptional, (1 review)
"Thoroughly enjoyed our stay! Room was clean, welcoming and relaxing. Hosts were pleasant, accommodating and kind. Would highly recommend. We will definitely be back! "
United States
Paula W.
The price is CA $89
CA $123 total
includes taxes & fees
Mar 4 - Mar 5
Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel

Apartment in Van Buren

Easy Street Apartment
10.0 out of 10, Exceptional, (2 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 $183
CA $300 total
includes taxes & fees
Mar 1 - Mar 2
Easy Street Apartment
The price is CA $181
CA $299 total
includes taxes & fees
Mar 2 - Mar 3
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

Apartment in Van Buren

Cozy Corner
10.0 out of 10, Exceptional, (3 reviews)
"The cutest place to stay after a long day on the river! Natalie was great, and the place was very clean and comfortable."
United States
Krista M.
The price is CA $183
CA $300 total
includes taxes & fees
Mar 1 - Mar 2
Cozy Corner
The price is CA $239
CA $475 total
includes taxes & fees
Mar 6 - Mar 7
Walk to Current River: Ozarks Adventure Home!
The price is CA $356
CA $425 total
includes taxes & fees
Feb 28 - Mar 1
H.D. Franks Guesthouse - Romantic Beautiful 2 Story 1946 Home
The price is CA $185
CA $444 total
includes taxes & fees
Mar 6 - Mar 7
Newly renovated family/pet-friendly Mountain View home
10.0 out of 10, Exceptional, (1 review)
"Absolutely perfect in every way, beautiful view! Host were very kind and helpful!!"
United States
Loretta B.
The price is CA $342
CA $492 total
includes taxes & fees
Mar 12 - Mar 13
Hilltop House #1 with AMAZING views
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.