Holiday rentals in Winona

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Top-rated holiday rentals in Winona

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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, 160 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
The exterior view of the house highlights a covered deck with both seating and dining areas. A fire pit is visible in the yard, surrounded by a grassy space. The home features a light-colored facade under a metal roof, with trees dotting the background.
Home in Eminence
4.94 out of 5 average rating, 120 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!

Guest favourite
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, 220 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.

Guest favourite
The exterior of the cabin is framed by tall trees, with a spacious upper deck adorned with string lights. A fire pit with a circular stone surround is located in the foreground, accompanied by a rustic wooden chair, inviting relaxation in a natural setting.
Treehouse in Salem
4.94 out of 5 average rating, 149 reviews

*Bronze Gabel Cabin Treehouse

Crafting an Experience - Welcome to The Bronze Gabel Cabin. Tucked away in the Salem/Rolla area this 15 acre woodland is a unique getaway awaiting. Explore nearby Fugitive Beach, Current River & the beautiful Montauk State Park. A cabin highlight is the wrapped upper decking for an memorable outdoor movie night or relax with your locally roasted coffee. At night, sit around the fire pit & listen to the sounds of the Ozarks. The Bronze is one of its kind & a perfect couples retreat.

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, 181 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, 249 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 favourite
Cabin in Williamsville
4.97 out of 5 average rating, 106 reviews

Cypress Bend cabin w/hot tub on Black River

Cozy new built cabin on a bend of the beautiful Black River. You’ll walk up the 14 stairs to a large screened in covered deck with hot tub and sitting area, and gas grill. The glass doors and windows allow you views of the river. The theme throughout is Indian-Aztec. Accommodates only two adults. If you’re looking for a peaceful/romantic get away this is the perfect place. Located approximately 2 hours south of St. Louis, and less than 15 minutes from Poplar Bluff, MO.

Top guest favourite
A charming cottage exterior is framed by a peaceful wooded setting. The screened porch features large windows, allowing for views of the natural surroundings. Potted plants enhance the entrance, alongside a rustic grill, while a welcome sign adds a personal touch to the inviting atmosphere.
Cottage in Summersville
4.99 out of 5 average rating, 118 reviews

Leona’s Cottage -Uniquely Rustic Comfortably Cozy

Leona’s Cottage is a unique hand built gem nestled in a peaceful wooded setting 2 miles down a quiet country road that’s surrounded by peaceful pastures and natural woodlands. The Cottage is a wonderful get-a-way for those looking for rustic charm but still wanting modern luxuries. Leona’s Cottage shares the road with Emily’s Cottage and is separated by a grove of trees far enough apart for total privacy but close enough for larger gatherings of up to 8 guests.

Guest favourite
An inviting interior view displays a cozy sleeping area featuring a quilted bedspread. A wood cabinet and a TV are visible, alongside a small dining set. An air conditioning unit provides comfort, while a coffee maker is positioned on a nearby shelf.
Tiny home in Salem
4.91 out of 5 average rating, 214 reviews

Delightful 1 bedroom peaceful tiny house

You won’t forget the peaceful surroundings of this rustic destination. Your stay with us is sure to bring you back to simplicity of life while comfortably cozy and relaxed . While TV and WiFi are available , you will find yourself content with viewing the activities of the surroundings and serene atmosphere. Just minutes away you’ll find exciting selections of activities , excellent dining , and friendly small businesses with a wide selection of interest .

Top guest favourite
The cabin exterior is viewed at night, featuring a well-lit entrance with a warm glow from the lantern. The wooden porch wraps around the front, leading to a door framed by large windows that showcase the cozy interior.
Cabin in Eminence
4.93 out of 5 average rating, 109 reviews

Robin’s Nest @ Current River/Jacks Fork River BYOH

Relax with the whole family at this peaceful cabin with a stay in the country or have a quiet, romantic getaway in a central area to explore Springs, Current and Jacks Fork Rivers, search for the Wild Horses or just relax and listen to the night sounds and look at the stars! A great location for whitetail deer and turkey hunting public lands of Missouri! If you want a place in a rural area away from the city lights, this is the place for you!!

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
4.98 out of 5 average rating, 127 reviews

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!

Top 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
4.94 out of 5 average rating, 188 reviews

Deadwood Acres Hideaway

This log cabin sets on 15 acres for you to enjoy the serenity and peacefulness while you vacation and relax. Ron is usually around to help cell 314-581-3243. The deck is a great place to just sit and relax and let the world pass by. 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.

Popular amenities for Winona holiday rentals

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