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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Guest favorite
Home in Eminence
4.93 out of 5 average rating, 128 reviews

2 bedroom close to Jacks Fork and Current River

Rivertown Retreat is located less than 2miles from the Jacks Fork River and a short drive to the Current. This 2 bedroom home is the perfect place to get away from the busyness of life and relax. Sit on the porch swing, grill on the BBQ or toss the frisbee around in the large yard. Whether you are in Eminence for a float trip down the river, to hike in one of the many state parks close by, to catch some trout in the river or just to relax and enjoy the Ozarks, Rivertown Retreat is here for you!

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Top guest favorite
A spacious brick-front home is presented with a gravel driveway and attached two-car garage. The structure features multiple skylights, enhancing natural light. A covered porch with seating invites relaxation, surrounded by lush greenery and trees, offering a serene outdoor setting.
Earthen home in Eminence
4.96 out of 5 average rating, 108 reviews

RockStack Retreat | Private 10 Acres · Jacks Fork

Escape to Rockstack, your own private retreat on 10 wooded acres minutes from the Jacks Fork River and Eminence. With no neighbors in sight, you'll enjoy rare quiet, space, and a true sense of seclusion. Spend your days floating the river or exploring nearby parks and trails, then return to peaceful surroundings and evenings by the fire under the stars. Ideal for families, friends' getaways, and small groups seeking a relaxing Ozark stay — with room for up to 10 to spread out and truly unwind.

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Top guest favorite
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
5.0 out of 5 average rating, 46 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!

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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, 197 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.

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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, 254 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.

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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
4.93 out of 5 average rating, 219 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!

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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
5.0 out of 5 average rating, 26 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.

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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, 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.

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Top guest favorite
Home in Eminence
5.0 out of 5 average rating, 37 reviews

House on Main Street! 1 mile to Jacks Fork river!

Entire 3BR house on Main Street, just 1 mile from Jacks Fork River! Fully stocked kitchen, washer/dryer, and cozy porch swing. Walk to shops/restaurants or explore springs, trails, Rocky Falls, and Mark Twain National Forest. Perfect for floating, hiking, horseback riding, or relaxing in the Ozarks. Enjoy privacy, a large backyard, and modern comforts in the heart of the Ozarks, Eminence,MO.

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Superhost
A cabin is presented with a green exterior and a metal roof. A staircase leads to a balcony featuring two outdoor chairs. The surrounding area is lush with trees, providing a natural backdrop. A small outdoor seating area is visible at the base.
Cabin in Alton
4.91 out of 5 average rating, 188 reviews

Kayden’s Cabin

We are a family owned cabin near the Eleven Point River! We are located exactly 11 miles from the intersection of 19 North and 19 South in Alton, Missouri on AA Highway. Our cabin sleeps six people with a queen size bed, one set of bunk beds, full size blow-up mattress, and a loveseat. We are about a mile and a half from Whitten Access. Please No smoking, pets, or partying.

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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
5.0 out of 5 average rating, 136 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.

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Guest favorite
Tiny home in Winona
5.0 out of 5 average rating, 10 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.

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