Winona Vacation Rentals from CA $164: Short-Term Rentals for 2025

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Vacation Rentals in Winona

"We chose this property for our 1st Christmas away from home. I traveled with my husband, 3 kids aged 10-17, and 2 dogs. Walking in the first thing we saw was the beautiful Christmas tree and the decorated screened in porch. The home was very clean and had everything we could possibly need. The furniture was comfy and there were plenty of places for everyone to sit and relax. The bedrooms were spacious. The closets provided more than enough space to hang the clothes we brought with us. These...

"The property is terrific -- we loved the river access -- and the hosts do a great job providing all the various amenities and tools to help make your stay fun and easy. Really nice hosts with great communication."

CA $533 total

includes taxes & fees

Feb 16 - Feb 17

"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!"

"Our stay was wonderful. The peace and tranquility of this place allows you to decompress completely. The spirit of the Lord resides here. The horses were beautiful and even the snow that fell was like God dressing the trees. We can't wait to return! The owner stayed in contact throughout our stay and the caretaker Adam was very accommodating!"

"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. "

"Nice place. Would stay again."

"The owners were very friendly and quick to respond to any questions. We came down for our annual sxs ride The weather was getting bad and they even offered a stay on them for another night if needed. The cabin- very spacious and perfect for any group size. Clean and adorable with all the furnishings. The view doesn’t get any better. We would definitely stay there again!! "

"Very nice cabin! Better than staying at a hotel, at near the same price."

"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."

"Very quiet and quant little cabin. Nice walk to the creek. Close to everything. Would stay there again "

"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."

CA $309 total

includes taxes & fees

Feb 2 - Feb 3

"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! "

"Very nice place to stay great view. The owners are great and very helpful. We got stuck in the snow and they went out of the way to assist us. Will stay again. "

"House is really lovely and comfortable, we (7 adults) had a wonderful stay. The view of the river is beautiful and the most intrepid in our group went down to the river's edge and said it was even more gorgeous down there."

"It was quite and relaxing. We really enjoyed it. "

"Clean and convenient "

"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"

"Loved this property. New home near town and hiking trails of the Ozark National Scenic Wayerways. Conveniences near by. Homes is in excellent condition and recently constructed with all new interior furnishings. Owner is excellent to work with. Responded to needs and questions immediately. "

CA $789 total

includes taxes & fees

Feb 2 - Feb 3

"This is a nice cabin in the woods. It's quiet, comfortable, and clean. There was nothing I didn't like. "

"Everything was clean and just as advertised. Ron was responsive and extremely nice. Love the area and would go back again and stay here."

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Other types of properties in Winona you may be interested in

"We chose this property for our 1st Christmas away from home. I traveled with my husband, 3 kids aged 10-17, and 2 dogs. Walking in the first thing we saw was the beautiful Christmas tree and the decorated screened in porch. The home was very clean and had everything we could possibly need. The furniture was comfy and there were plenty of places for everyone to sit and relax. The bedrooms were spacious. The closets provided more than enough space to hang the clothes we brought with us. These...

"I've been staying at Echo Bluff for years, always in January or February. It's always been wonderful. We live about an hour away. During the spring, summer and fall we'll pack a picnic, drive up for the day and hike. It's always a good time. And the staff is excellent, always friendly and helpful. My only complaint is the restaurant. The food is always good but the menu is limited. I wish there was more variety. However, this doesn't keep me from coming back. I' m already planing my trip for...

CA $188 total

includes taxes & fees

Feb 6 - Feb 7

"One of the best along highway 60 in MO"

CA $172 total

includes taxes & fees

Feb 2 - Feb 3

Find out more about Winona

Everything you need to know about Winona vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winona vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winona vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winona vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winona. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona vacation rentals we have selected for you start as low as CA $164 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Winona rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winona vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winona. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Winona Vacation Rental Travel Info

Popular accommodation	Winona private vacation homes
Known landmarks	Rocky Falls
International airports	St. Louis, MO (STL-Lambert-St. Louis Intl.) and Fort Leonard Wood, MO (TBN-Waynesville Regional)

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.

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Winona Vacation Rentals

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Check prices for these dates

Vacation Rentals in Winona

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

#ContemplationCabin on the Jacks Fork River!

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

Secluded Eminence Ranch House Cabin in the Ozarks

The Cabin on Current River with Private Gravel Bar!!

RIVER FRONT HOUSE

Ozark Oasis 3 B/ 3 B in Eminence with Spectacular View!

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

Secluded Ozarks Tiny House cabin in Eminence, MO

Deadwood Acres cabin #2

Quiet 2 story Cabin on 32 acres near eleven point river

Deadwood acres cabin #3

Private Hilltop Cabin Near Current River

Family-friendly Cabin w/150 ft Current River frontage in Ozark Scenic River

Secluded Ozarks Bunk House Cabin at Old Desperado Ranch

Spacious 4 bedroom cottage near Current River

New cabin located on the jacks fork river front.

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

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

Deadwood Acres cabin #1

Other types of properties in Winona you may be interested in

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

Echo Bluff State Park

Honeysuckle Inn - Mountain View

Find out more about Winona

Winona Vacation Rental Travel Info

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