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Vacation rentals in Winona

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winona

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A lush green lawn is highlighted, dotted with trees and shrubs. In the distance, a treehouse structure and a pavilion are visible, surrounded by nature. A small garden area with diverse foliage is positioned in the foreground, contributing to the serene outdoor setting.
Treehouse in Bunker
4.96 out of 5 average rating, 165 reviews

Almost Heaven Treehouse

Featured in St Louis Magazine Spring 2022! Previously Parade Magazine and Only in Missouri! Nestled on the banks of Big Creek in the heart of the Missouri Ozarks and the Roger Pryor Pioneer Back Country, sits the Almost Heaven Treehouse. This quaint and rustic space is a must visit for those who love the great outdoors. Whether you want to relax in the creek, swim, hike, fish, paddle float,or ride atvs or s x s, this is the place for you!! This cabin is located 6 miles off pavement.

Top guest favorite
The exterior of a modern cabin is showcased, featuring a dark facade with a metal roof. A spacious front porch is lined with comfortable seating, while lush green grass surrounds the structure, enhancing the serene and natural setting among the trees.
Cabin in Houston
4.97 out of 5 average rating, 179 reviews

2 bedroom cabin nestled in the Shady pines

Take it easy at this unique and tranquil getaway. This newly built Cabin with a loft sits on 3 wooded acres overlooking a small stocked pond. Just minutes from Big Piney River, Mark Twain national Forest, and Ozark National scenic River ways! Nestled in the pines on the outskirts of town you will think you are hours from anyone! Sit around the fire pit by the pond and enjoy the sights and sounds of nature! Piney River Brewery is just minutes away with River access in almost every direction!

Top guest favorite
Guesthouse in Mountain View
5 out of 5 average rating, 24 reviews

New! Guest house on our farm. No cleaning fee!

Guest favorite! Whether you need a place to just relax and enjoy nature, or a place to rest while driving through. Come paddle, ride, hike, hunt. Fully stocked kitchen with stove,coffee pot, microwave, refrigerator, and toaster oven. Pans dishes etc. Pet friendly. Room for large trailers. Two large RV pads. No hook ups at this time but in a pinch, we can accommodate for water and power if needed.. Go to sleep to the sounds of frogs and crickets, wake up to birds. Peaceful and private.

Guest favorite
A secluded cabin is nestled among the trees, featuring a spacious wooden deck that invites relaxation. Sunlight filters through the leaves, creating a serene ambience. The surrounding natural landscape showcases a gentle slope leading up to the cabin.
Cabin in Eminence
4.93 out of 5 average rating, 222 reviews

Secluded Ozarks Cabin in the woods - Eminence MO

Experience complete serenity in the middle of the beautiful Ozark Mountains near some of the clearest rivers and streams. Whether you just want a quiet get away to take in all nature has to offer or you want to float, kayak, trail ride, hike, fish, boat, sxs ride, explore beautiful springs, search for the wild horse herds or just do nothing! Western saloon on site offering all types of cold drinks, pizza, ice cream, snacks. Limited hours/by request. Horseback riding available by RSVP.

Top guest favorite
The living area features warm wooden walls and a high, exposed beam ceiling. Comfortable seating is arranged around a patterned area rug. A wall-mounted television is present, along with a small table and fishing gear, providing a cozy and functional space for relaxation.
Cabin in Salem
4.95 out of 5 average rating, 125 reviews

Blue Ribbon Trout Cabin at Montauk

Enjoy your own personal park space with Current riverfront access. This cozy three bedroom, one bath cabin is uniquely situated on 3 acres within National Park land boundaries just outside one of Missouri's premiere trout parks. Montauk State Park is just minutes away. You can take a float trip, swim in the clear cool waters of the Current river, relax by the riverside fire pit or just sit on the deck and take in the natural beauty of the Ozarks National Scenic Riverways.

Superhost
A small cabin exterior is shown, featuring a covered porch with green chairs and a small charcoal grill. The porch is framed by a wooden structure, with gravel pathways leading to a landscaped yard surrounded by trees.
Cabin in Eminence
4.78 out of 5 average rating, 193 reviews

Cabin Near the Ozark Rivers

Small cabin with its own private setting, just outside of city limits. 2.5 miles from town and the Jacks Fork River. Nice sized yard with a fireplace for your use. Plenty of on site parking and near by thousands of acres of public land. Whether you’re looking to float the river, recreate on public land, explore the caves and springs of Missouri, or just enjoy some peace and quiet, this is the place for you. The home is adjacent to Highway 106 on the west side of Eminence.

Guest favorite
A cozy cabin is set in a private country setting, featuring a large stone fireplace and a screened-in porch. Surrounding foliage and lush grass complement the cabin's rustic charm, while a gravel path leads to the entrance.
Cabin in Birch Tree
4.88 out of 5 average rating, 250 reviews

❤️ Pine Hollow Cabin Eminence Missouri

Deep in the Ozarks Eminence is world famous for it's natural beauty and recreational activities. We offer a very cozy cabin with full kitchen, washer/dryer, screened in porch, stone fire place in private country setting. We are 3 miles down a gravel road which gives us lots of privacy and very little traffic. There is very little cell service but we have WiFi. We are located just 10 miles outside of Eminence, and the cabin sets atop a valley over looking our pastures.

Top guest favorite
A wooden bench is positioned near the riverbank, adorned with vibrant flower pots and a decorative pillow featuring a bird design. The calm water of the Jacks Fork river is visible, framed by trees in early foliage.
Cabin in Mountain View
4.95 out of 5 average rating, 212 reviews

#ContemplationCabin on the Jacks Fork River!

This is a cozy riverfront cabin which is 1 of 2 separate cabins located on 25 acres near the "Barn Hollow Natural Area" just 8 miles outside Mountain View Missouri. While looking out over the Jacks Fork river from the cabin you can hear the soothing sound of the river flowing. The river access for swimming, crackling wood burning stove, and hot tub are just some of the many things about this cabin that you are sure to love!

Guest favorite
A spacious living area features a large sectional sofa with decorative pillows, a coffee table, and a flat-screen television. The stone fireplace adds warmth to the room, complemented by wall mirrors. Soft lighting creates a comfortable environment for relaxation and gathering.
Home in Winona
5 out of 5 average rating, 20 reviews

3 BD 2 bath family home

Bring the whole family to this great place with lots of room for fun. Enjoy all that Shannon County has to offer.. Drive just 11 miles to the best swimming hole in the Ozarks, Rocky Falls Shut ins. From there you can go hiking on the Ozark Trail and look at the elk. If you prefer to float, the Current River and Jacks Fork are just 15 minutes away. Come relax in our home away from home in the heart of river country.

Guest favorite
A rustic log cabin is set amidst a wooded area, featuring a welcoming front porch with wooden steps and railings. The natural landscape includes gravel pathways and large rocks, enhancing the cabin's secluded appearance. A hammock hangs nearby, inviting relaxation.
Cabin in Eminence
4.93 out of 5 average rating, 193 reviews

Deadwood Acres Hideaway

This log cabin sits on 15 acres for you to enjoy serenity and peacefulness while you vacation and relax. Ron is usually around to help if you have an issue. The deck is a great place to just sit and relax and let the world pass by. There is a spring fed Creek Runs along the edge of the property and is great for just sitting and relaxing. There is a BBQ pit and fire pit on site. Pets are welcome.

Top guest favorite
A large, double slipper clawfoot tub is positioned against a backdrop of rustic wooden walls. A stylish mirror reflects the room, while a small chair sits nearby. A modern electric fireplace adds a touch of warmth, and soft lighting illuminates the space.
Home in Birch Tree
5 out of 5 average rating, 126 reviews

The Aviary Retreat

Newly renovated 1900’s farmhouse with attention to detail. Historic home with current new fixtures. This gorgeous home has beautiful bathroom with a large shower and a double slipper clawfoot tub. We hope you enjoy your stay in our fully restored historic home. Only a short walk to restaurant and bar. There is a security camera on property outside beside backdoor.

Top guest favorite
Home in Birch Tree
5 out of 5 average rating, 12 reviews

CountryComfortRetreat

Relax with the whole family at this peaceful country getaway! Spend your evenings unwinding while watching all kinds of wildlife right from your doorstep after a full day of adventure and river fun. The spacious yard is perfect for kids to run, play, and burn off all that extra energy! If you love the outdoors, this is the perfect place for you.

Popular amenities for Winona vacation rentals

  1. Airbnb
  2. United States
  3. Missouri
  4. Shannon County
  5. Winona