Winona Vacation Rentals

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Our top choices for Winona vacation rentals

Walk to Current River: Ozarks Adventure Home!

Walk to Current River: Ozarks Adventure Home!
3.0 star property
Van Buren
The price is CA $168
CA $375 total
includes taxes & fees
Apr 16 - Apr 17
Walk to Current River: Ozarks Adventure Home!

#ContemplationCabin on the Jacks Fork River!

#ContemplationCabin on the Jacks Fork River!
Summersville
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 $344
CA $496 total
includes taxes & fees
Apr 22 - Apr 23
#ContemplationCabin on the Jacks Fork River!

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, (35 reviews)
"Beautiful property, I’d recommend to anyone going here to stay here."
United States
tom
The price is CA $165
CA $202 total
includes taxes & fees
Apr 16 - Apr 17
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

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, (19 reviews)
"Host was very welcoming. We are an outdoors centric family and this was better than camping…very secluded and peaceful location. "
United States
Troy S.
The price is CA $157
CA $312 total
includes taxes & fees
Apr 20 - Apr 21
Quiet 2 story Cabin on 32 acres near eleven point river

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, (12 reviews)
"Wonderful stay. Good location. Very enjoyable experience."
United States
Thomas H.
The price is CA $434
CA $804 total
includes taxes & fees
Apr 16 - Apr 17
Living Waters Estates, Elegant 3 BR Home with kids area, hot tub, sleeps 12

Newly renovated early 1900’s farmhouse

Newly renovated early 1900’s farmhouse
Birch Tree
10.0 out of 10, Exceptional, (23 reviews)
"Place was perfect for our stay. Beautiful property. "
United States
Drew W.
The price is CA $221
CA $393 total
includes taxes & fees
Apr 16 - Apr 17
Newly renovated early 1900’s farmhouse

Hilltop House #1 with AMAZING views

Hilltop House #1 with AMAZING views
Van Buren
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 $344
CA $497 total
includes taxes & fees
Apr 22 - Apr 23
Hilltop House #1 with AMAZING views

Charming 2-bedroom house with AC, WiFi in serene Van Buren

Charming 2-bedroom house with AC, WiFi in serene Van Buren
Van Buren
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 $232 total
includes taxes & fees
Apr 22 - Apr 23
Charming 2-bedroom house with AC, WiFi in serene Van Buren

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
10.0 out of 10, Exceptional, (1 review)
"Lots of room, recently remodeled and up to date. Fully stocked with just about everything you need. Host quick with response. Close to the current river, big springs national park and downtown businesses "
United States
Angela W.
The price is CA $217
CA $343 total
includes taxes & fees
Apr 16 - Apr 17
Family-Friendly 3BR/2BA Van Buren Home w/ Fire Pit & Starlink WiFi!

Cozy quiet country getaway just minutes from the Current River

Cozy quiet country getaway just minutes from the Current River
Van Buren
10.0 out of 10, Exceptional, (1 review)
"Was a great little cabin"
United States
Ann C.
The price is CA $112
CA $204 total
includes taxes & fees
Apr 16 - Apr 17
Cozy quiet country getaway just minutes from the Current River

H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo.

H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo.
Alton
The price is CA $279
CA $340 total
includes taxes & fees
Apr 21 - Apr 22
H.D. Franks Guesthouse - Romantic Vintage Colonial Home in Historic Alton Mo.

Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel

Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel
Alton
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 $124
CA $162 total
includes taxes & fees
Apr 21 - Apr 22
Melody King Suite. Experience peaceful relaxation in this Micro Boutique Hotel

Cozy Corner

Cozy Corner
Van Buren
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 $185
CA $302 total
includes taxes & fees
Apr 16 - Apr 17
Cozy Corner

Easy Street Apartment

Easy Street Apartment
Van Buren
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 $185
CA $302 total
includes taxes & fees
Apr 16 - Apr 17
Easy Street Apartment

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
9.4 out of 10, Exceptional, (18 reviews)
"Very convenient location for us. The cabin is perfect for two people. "
United States
Cynthia A. S.
The price is CA $211
CA $317 total
includes taxes & fees
Apr 28 - Apr 29
Just A Stone's Throw Cabin from Eminence, Jacks Fork, & Cross County Trail Ride

Walk to Current River: Ozarks Adventure Home!

Walk to Current River: Ozarks Adventure Home!
Van Buren
The price is CA $151
CA $380 total
includes taxes & fees
Apr 16 - Apr 17
Walk to Current River: Ozarks Adventure Home!

Newly renovated family/pet-friendly Mountain View home

Newly renovated family/pet-friendly Mountain View home
Mountain View
The price is CA $186
CA $444 total
includes taxes & fees
Apr 26 - Apr 27
Newly renovated family/pet-friendly Mountain View home

Hilltop House #2

Hilltop House #2
Van Buren
9.4 out of 10, Exceptional, (3 reviews)
"Beautiful property. Would stay again."
United States
Sharon P.
The price is CA $222
CA $349 total
includes taxes & fees
Apr 27 - Apr 28
Hilltop House #2
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?

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