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Winona Holiday Rentals

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Holiday Rentals in Winona

“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.

10.0 out of 10, Exceptional, (11)
"Had a great time. Loved the privacy and all the stocked kitchen amenities. AC was cold. That shower was amazing. Quiet retreat in proximity to Rocky Falls and our float trip on Jack's Fork! "
“The Cabin”@ Serenity Ranch. Centrally located to all the wonders of Shannon co.

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

10.0 out of 10, Exceptional, (71)
"The house was so comfy and well-stocked with everything we needed. It rained all weekend but we had lots of fun playing games in the barn and card games in the house. Loved the fire pit, creek, and screened in porch, too. The area around Eminence is beautiful with lots of springs, pretty rivers, good hikes, and even wild horses. Wonderful hosts and fun weekend!"
Shawnee Creek Hideaway - Close to Eminence and the Jacks Fork River!

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

9.4 out of 10, Exceptional, (23)
"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 !

Collier Cabin in Pine Hollow ~ Eminence, MO

9.8 out of 10, Exceptional, (19)
"Best host’s around and a very private peaceful cabin. Everything about this place is great. Second time staying there and I will definitely be back!"
Collier Cabin in Pine Hollow ~ Eminence, MO

Springside Cottage in beautiful Eminence. Great outdoor space - NEW Hot tub!

9.8 out of 10, Exceptional, (12)
"My fiancè and I had a lovely time staying at this cute little cottage. The location is perfect. It's tucked away but close enough to all there is to see and do in Eminence. The hot tub in the patio with the tv was so cool. I definitely would stay here again!"
The price is AU$361
includes taxes & fees
6 Oct - 7 Oct
Springside Cottage in beautiful Eminence. Great outdoor space - NEW Hot tub!

Beautiful 3-bedrm , 3.5 ba Log/Stone in Eminence MO. Will sleep up to 16 guests.

9.8 out of 10, Exceptional, (7)
"Great space!"
Beautiful 3-bedrm , 3.5 ba Log/Stone in Eminence MO. Will sleep up to 16 guests.

Unbeatable convenience in amazing Eminence!

10.0 out of 10, Exceptional, (17)
"Everything was very nice and cozy and also convenient."
Unbeatable convenience in amazing Eminence!

Unique cabins in the woods<br>Not friendly for Street Bikes.

10.0 out of 10, Exceptional, (107)
"Very nice people and place"
Unique cabins in the woods<br>Not friendly for Street Bikes.

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

9.6 out of 10, Exceptional, (15)
"Good location and really nice place"
Pine Perfect Cabin on the edge of town only 1/2 mile from Current River!

Fox Pen Cabins Cabin #2 Not friendly for street bikes… Pet-Friendly

3.0 star property
10.0 out of 10, Exceptional, (6)
"Great little cabin, roads to cabin not the best but worth it!"
Fox Pen Cabins Cabin #2 Not friendly for street bikes… Pet-Friendly

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

10.0 out of 10, Exceptional, (32)
"Beautiful property, I’d recommend to anyone going here to stay here."
The price is AU$209
includes taxes & fees
27 Oct - 28 Oct
Clearwater Lake, cabin minutes from Bluff View Marina & boat dock

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

8.8 out of 10, Excellent, (14)
"Love Current River! Love this location to stay!!"
Lazy River Cabin on the edge of town only 1/2 mile from Current River !

Chasen Summer! 1/2 Mile from Current River!

9.4 out of 10, Exceptional, (38)
"Everything was great, great accommodations we loved out stay"
Chasen Summer! 1/2 Mile from Current River!

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

2.0 star property
9.0 out of 10, Wonderful, (13)
"Lovely little house that fit our needs for a few days during a family reunion. Very quick access to a Dollar General, liquor store and gas station. And only a couple quick miles to the Landing. "
The price is AU$260
includes taxes & fees
30 Sept - 1 Oct
Charming 2-bedroom house with AC, WiFi in serene Van Buren

The Loft on the River with Private Gravel bar!!

8.0 out of 10, Very good, (19)
"We had a great time and other than there was no broom so hard to sweep the sand from the beach, but that was very minor. Overall it was clean and we all enjoyed it! Will come back again next year!"
The Loft on the River with Private Gravel bar!!

Quiet 2 story Cabin on 32 acres near eleven point river

10.0 out of 10, Exceptional, (15)
"Had a great time. Really nice place, great to have WiFi. If you have AT&T the WiFi in area is not the greatest. You will have if At the house. Enjoyed visiting, hiking Mark Twain National Forest. The host was so kind and helpful. Family enjoyed the little getaway. "
The price is AU$330
includes taxes & fees
28 Sept - 29 Sept
Quiet 2 story Cabin on 32 acres near eleven point river

Triple H Properties

8.6 out of 10, Excellent, (27)
"Worked out great for friends to stay for a float trip weekend. "
Triple H Properties

Cabin in the heart of the Ozark National Scenic Riverway!

10.0 out of 10, Exceptional, (55)
"All of my friends love staying here for our annual float trip. The cabin is decorated beautifully and the porch is our favorite spot to visit with each other. It’s the perfect place to create lasting memories. "
Cabin in the heart of the Ozark National Scenic Riverway!

Secluded Ozarks Tiny House cabin in Eminence, MO

9.6 out of 10, Exceptional, (99)
"My husband, young children (6 and 4), and I enjoyed our stay. The cabin was cute and clean. Great place to stay."
Secluded Ozarks Tiny House cabin in Eminence, MO

Deadwood Acres cabin #2

9.8 out of 10, Exceptional, (36)
"This place is a hidden gem we will def be back!"
Deadwood Acres cabin #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

Find out more about Winona

Everything you need to know about Winona holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winona holiday rental for you. At Expedia, you can take your pick from private holiday 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winona holiday 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winona holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winona holiday rentals we have selected for you start as low as AU$209 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winona rentals

At Expedia, we put the best Winona holiday 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 holiday.

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. 

Frequently asked questions

Are there holiday rentals in Winona?

Yes, there are holiday rentals close to the most popular sights in Winona, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winona has to offer?

Beautiful 3-bedrm , 3.5 ba Log/Stone in Eminence MO. Will sleep up to 16 guests.: This holiday home rental outside of Winona is located on a river, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 holiday rental in Winona like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winona. Holiday rentals offer amenities such as laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a family trip or a small group gathering.