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Vacation rentals in Winona

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Top-rated vacation rentals in Winona

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Top guest favorite
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, 117 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 favorite
A gravel area features a wooden picnic table and several Adirondack chairs arranged around a fire pit. The cabin is elevated on a wooden platform in the background, surrounded by lush trees, creating a secluded atmosphere.
Cabin in Eminence
4.97 out of 5 average rating, 140 reviews

Secluded Ozarks Bunk House at Old Desperado Ranch

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! Book The NEW Bunk House cabin at Old Desperado Ranch. The Bunk House is a studio type cabin with beautiful western cowboy decor! 4 horse stalls to rent.

Top guest favorite
A modern studio apartment is depicted from an outdoor angle, showcasing a vibrant green exterior. A wooden staircase with a railing leads to a second-level entrance. Gravel pathways surround the structure, and the sky is filled with clouds, suggesting evening light.
Place to stay in Cabool
4.97 out of 5 average rating, 158 reviews

COUNTRY LACE Retro Place

Our Country Lace Retro Place is a quaint little studio apartment nestled upstairs overlooking our rolling hills of the Ozark’s with abundant Wild Life (which can be scene early in the mornings or late evenings) and foliage ….furnished with a toaster, microwave, refrigerator, coffee maker and a Nija Flip up air fryer oven. Full bath with a furnished hair dryer and linens. Living space includes a king size bed, sofa and a oversized chair. We also have WIFI and our custom made retro TV….

Guest favorite
The Bronze Gabel Cabin features a two-story structure nestled among trees, showcasing large windows and a spacious upper deck. String lights create a warm ambiance around the porch area, while the surrounding forest adds to the secluded atmosphere, inviting guests to relax outdoors.
Treehouse in Salem
4.94 out of 5 average rating, 137 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, 179 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 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, 248 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 favorite
A cozy room features a spacious bed adorned with a colorful patterned quilt. Decorative shelves display various items, while framed pictures and wall art enhance the ambiance. A small television is mounted, and a patterned rug lies on the floor, adding warmth to the setting.
Tiny home in Eminence
4.93 out of 5 average rating, 107 reviews

Lil Villa Delightful tiny home for couples

No cleaning fee! Lil Villa is Summerside’s little sister and has room for a couple. She’s not a large space, but she’s clean, cute and very nice, like all little sisters. She has a full bathroom just a short walk down a lighted path. Bathrobes are provided for guests. She doesn’t like the words tiny house because it hurts her feelings. You can relax outside in her private courtyard, by the creek on the property or have a campfire. Parking is on the premises.

Top guest favorite
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, 107 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 favorite
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, 175 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!!

Top 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, 184 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.

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 out of 5 average rating, 114 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.

Top guest favorite
A cozy living area features a stone fireplace surrounded by wooden walls and large windows. Comfortable seating arrangements include a beige couch, armchairs, and a wooden coffee table. Natural light fills the space, enhancing the cabin feel, with a view of the outdoors visible through the windows.
Home in Van Buren
4.98 out of 5 average rating, 113 reviews

Luxury Log Cabin: 5 bedroom Van Buren River Cabin

Luxury log cabin near Big Spring, the Current River & Ozark National Scenic Riverways—just 1 mile from town! 5 bedrooms (1 king, 3 queen, 1 twin bunk), 3 full baths, two large living rooms, fireplace, outdoor kitchen, gas fire pit & scenic views. Family-friendly with yard games & kid amenities. Explore river fun with local outfitter, The Landing.

Popular amenities for Winona vacation rentals

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