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
Cabin in Elizabeth
4.99 out of 5 average rating, 102 reviews

Secluded Lakefront Estate | Couples Retreat

Welcome to Sunset Cove on Norfork Lake, a secluded 60-acre gated lakefront estate where modern luxury meets untouched Ozark wilderness. Designed for couples seeking a rare escape where time slows, distractions fade, and world feels far. Mornings unfold slowly and evenings are peaceful, with sweeping lake views throughout the day. Spend your time exploring together between the water, hot tub, and quiet lakeside spaces in nature — a setting designed for stillness, connection, uninterrupted moments

Top guest favourite
Home in Eminence
4.94 out of 5 average rating, 121 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!

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
4.97 out of 5 average rating, 159 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 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.
Earth homes in Eminence
4.96 out of 5 average rating, 105 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.

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, 114 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! 3 miles up the road is Robin’s Roost Cabin. If you want a place in a rural area away from the city lights, this is the place for you!!

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, 183 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, 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 favourite
Cabin in Williamsville
4.97 out of 5 average rating, 109 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
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 homes in Salem
4.91 out of 5 average rating, 218 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
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, 129 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 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, 206 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 green cabin is situated amidst a grassy landscape, bordered by trees. A gravel path leads to the cabin, with a fire pit visible in the background. The area is well-maintained, showcasing the natural surroundings.
Cabin in Alton
4.91 out of 5 average rating, 184 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. **70.00 A Night**NO CLEANING FEE!!

Popular amenities for Winona vacation rentals

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