Holiday rentals in Winona

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Top-rated holiday rentals in Winona

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

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Top guest favourite

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

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.

FamilyLocationBeach

4.96 out of 5 average rating, 110 reviews

Top guest favourite

A spacious living area is highlighted by a light-colored sectional sofa adorned with patterned cushions. A dark wood coffee table sits on a decorative area rug. Walls are painted in calming shades, complemented by elegant curtain drapes. A modern ceiling fan and wall-mounted TV add functionality.

Home in Mountain View

The Executive Home

Your Ozarks getaway starts here! Enjoy this beautifully renovated 3-bedroom, 2-bath home in Mt. View, Missouri, with comfortable furnishings & fully stocked kitchen. Just minutes from downtown Mt. View,, Walmart, restaurants, and the hospital, the home also makes a great home base for exploring the Ozarks. Eminence is 35 minutes away, putting you within an easy drive of some of the area’s most popular floating, swimming, hiking, and outdoor destinations along the Jacks Fork and Current Rivers.

LocationValueIndoor spaces

4.99 out of 5 average rating, 78 reviews

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

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!

LocationFamilyCondition

5.0 out of 5 average rating, 47 reviews

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

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.

ValueFamilyParking

4.78 out of 5 average rating, 200 reviews

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

❤️ 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.

ValueFamilyLayout

4.88 out of 5 average rating, 255 reviews

Top guest favourite

A quaint cottage with a metal roof is surrounded by trees and open space. The structure is complemented by a nearby silo and a parking area with gravel. Natural light enhances the peaceful outdoor setting, with sparse landscaping and a picnic table visible in the foreground.

Cottage in Couch

Garfield Getaway LLC

Newly added 2nd bathroom and laundry attached to the cottage in a Grain Bin! Relax with the whole family in this peaceful country setting located approximately 10 miles from the beautiful Eleven Point River, well known for its canoeing, kayaking and fishing. Enjoy cooking on the grill and s’mores by the firepit. Also enjoy the Mark Twain National Forest with its beautiful hiking trails and natural springs. Party’s not allowed!

LocationValueHospitality

4.98 out of 5 average rating, 147 reviews

Top 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

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.

FamilyValueOutdoor spaces

5.0 out of 5 average rating, 28 reviews

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

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.

ValueFamilyHiking

4.93 out of 5 average rating, 199 reviews

Top guest favourite

Home in Eminence

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.

LocationFamilyParking

5.0 out of 5 average rating, 39 reviews

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

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.

FamilyLocationSleep quality

5.0 out of 5 average rating, 137 reviews

Guest favourite

Tiny home in Winona

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.

LocationValueDecor

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in Birch Tree

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.

LocationValueHiking

4.96 out of 5 average rating, 25 reviews