Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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

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Top guest favourite
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, 167 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 favourite
Two white chairs are positioned near a circular fire pit, surrounded by stones, along the edge of a peaceful lake. The calm water reflects the vibrant colors of the surrounding trees, while a gentle slope leads to the forested hillside in the background.
Home in Salem
4.9 out of 5 average rating, 346 reviews

Beaver Lake House-Welcome to Social Distance Land!

Unique remote location on family farm. A secluded stone house with 50 ' deck overlooking Beaver Lake. Watch & hear amazing wildlife! Open kitchen, dining/living room, woodstove, tile floors 2 bedrooms; larger with queen, smaller 2 twin beds, 2 sofa beds in living room. 2 new bathrooms, laundry room, picnic table, BBQ, access to Sinking creek, 9 acre lake to fish & 400 acre farm to explore! For additional accommodation check out The Mushroom Loft House across the creek also available on Airbnb.

Top guest favourite
The cabin is constructed with natural wood and stone, featuring a welcoming front porch. A spacious gravel area surrounds the cabin, complemented by a circular stone fire pit. The setting includes a backdrop of trees, creating a sense of privacy and tranquility.
Cabin in Houston
4.98 out of 5 average rating, 170 reviews

River Bluff Hideaway

River Bluff Hideaway is a brand new construction located on a private lane overlooking the Piney River in the Ozarks. The cabin is equipped with all the modern amenities you need for a comfortable stay, including a fully equipped kitchen, comfortable beds, and a cozy living room. Whether you’re looking to relax on the porch and take in the stunning river views or explore the nearby hiking trails, River Bluff Hideaway is the perfect place to unwind and recharge. You may even see some eagles 🦅

Top guest favourite
A dining area is presented with a wooden table surrounded by six black chairs, set with placemats. A ceiling fan with lights provides illumination, while a wall-mounted sign reading 'WELCOME' enhances the welcoming feel. Natural light enters through two windows adorned with blinds.
Cottage in Winona
5 out of 5 average rating, 45 reviews

Shawnee Creek Hideaway near the Jacks Fork River!

The Shawnee Creek Hideaway sits on 3 acres and is located on the spring fed Shawnee Creek. We are five minutes to downtown Eminence and the Jacks Fork River. Rocky Falls, Alley Mill and Spring, Klepzig Mill, Peck Ranch (Elk), and other springs and the Current River are a short drive from the house. The famous Ozark wild horse herds are also nearby. Floating, fishing, hunting, horseback riding and off road trails await you. Explore the best of the Ozarks from your Shawnee Creek Hideaway!

Top guest favourite
Guesthouse in Mountain View
5 out of 5 average rating, 27 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.

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, 196 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 favourite
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, 252 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.

Guest favourite
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
4.94 out of 5 average rating, 214 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 favourite
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, 23 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 favourite
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, 195 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 favourite
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, 132 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.

Guest favourite
Tiny homes in Winona
5 out of 5 average rating, 7 reviews

The Green Cabin - Cozy Getaway in the Ozarks

Cozy cabin nestled in the scenic Ozarks, surrounded by nature and close to Mark Twain National Forest. Ideal for a peaceful getaway with hiking, springs, and rivers nearby. Features a queen bed, sofa bed, and a fully equipped kitchen. Starlink internet available (weather dependent). Quiet, private setting. No hunting on property. Driveway camera for security.

Popular amenities for Winona vacation rentals