Holiday houses in Winner

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Top-rated holiday rentals in Winner

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

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Superhost
A welcoming living area features a comfortable sofa and a black recliner. A dining table with four chairs is positioned near a large clock on the wall. Light comes in through the windows, illuminating the wood flooring and neutral wall tones.
Home in Fairfax
4.82 out of 5 average rating, 105 reviews

Entire house for fishing, hunting, or passing by!

Perfect location for the outstanding fishing on the Missouri River and the great deer and pheasant hunting that Gregory county is known for! Within 15 to 25 minutes of four different boat ramps on the river! Double carport to keep your boat or vehicles under cover! Located on five lots so plenty of room to park or just enjoy the outdoor room. Quiet small town with extremely friendly residents! Also perfect for anyone just passing by for the night! “N0”TV in house or Wi-Fi but great cell service.

Top Guest favourite
The spacious living area features vaulted ceilings with wooden beams and large windows allowing natural light. A stone fireplace is located at the center, and a flat-screen TV is mounted above. Two sets of sliding glass doors lead to outdoor views.
Cabin in Chamberlain
5 out of 5 average rating, 65 reviews

The Log Cabin

Log cabin just minutes away from the Missouri River, public beach, marina & airport. Plenty of indoor and outdoor space for entertaining. Perfect for family gatherings, fishing and hunting trips. This This three-story cabin can sleep up to 14, includes 5 bedrooms, 10 beds and 3 bathrooms. Fully loaded kitchen with plenty of seating, front/rear decks and walkout basement. Large loft. Garage has game room with mini pool table & foosball. Outdoor propane grill, large yard, swing set & playhouse.

Superhost
The exterior of the house features a charming two-story design with a dark blue facade. A set of wooden stairs leads to a welcoming entryway, adorned with a small flower planter. Lush greenery surrounds the property, providing a serene atmosphere.
Home in Winner
4.87 out of 5 average rating, 100 reviews

Cozy Little Getaway

*if calendar does not show availability for your desired dates please direct message me regarding availability Relax with the whole family at this peaceful place to stay. Great location, centrally located in Winner. 5 bedroom 1.5 bathroom. Fully stocked with anything & everything you may need for your stay. *Pets are allowed with $50 non-refundable fee. This will be added to your invoice. Pets are allowed in heated laundry room, or in the front porch, not in the main part of the house.

Guest favourite
A cozy living room features a combination of soft furnishings, including a pair of recliners and a mix of sofas. Lighting is provided by side lamps, and artwork adorns the walls, including a mounted deer head. A patterned area rug adds color to the neutral space.
Home in Gregory
4.94 out of 5 average rating, 18 reviews

The Lodge

Located on the Edge of town in Gregory, South Dakota. pop 1250. A great place to stay when visiting the area or family. Large grassy yard, easy to find, clean and comfortable. We have an outdoor space with tables and a grill. Gregory County is in the Pheasant Triangle, Known for Big Whitetail, and is 35 mins from the Missouri River. Pets are allowed Outdoors in the kennel area. Please no pets indoors. Please send us a message if you have any questions or need help with a booking.

Top Guest favourite
A rustic living space features a leather sofa, adorned with a decorative blanket. A wooden coffee table, decorated with greenery, sits in front. Exposed wooden beams and a corrugated metal ceiling are visible, along with stairs leading to an upper level.
Barn in Colome
5 out of 5 average rating, 8 reviews

The Old Hayloft

Adventure awaits you in this rustic getaway. Just a short drive off of HWY 183 south of Colome to stay in this super cute old hayloft that had been renovated as guest quarters. Stair access externally. This is not handicap accessible and very rustic. It is on the second story. 2 bedroom 1 bath. Full bed in bedroom #1 and a set of twin beds in bedroom 2 and the third bedroom is an open loft (no door up steeper stairs) with another set of twin beds. Total guests is up to 6.

Top Guest favourite
A covered patio area features a mix of red and green outdoor seating options, inviting relaxation. The exterior of the dwelling is a muted green with a metal roof, surrounded by natural landscaping. A light-colored concrete surface is visible in front of the entrance.
Tiny home in Platte
4.99 out of 5 average rating, 152 reviews

Carriage House - Private Dwelling. 3 beds, 1 bath

The Carriage House is a private, separate dwelling located on the property of Molly's Manor B&B. Unique and comfortable, 525 sq. ft. No step entry. Main floor includes a bedroom with one Queen-size bed, a cozy living room, fully equipped kitchen with appliances and cookware, and bathroom with a large shower; W/D. Two full-size beds in the upstairs loft, including a futon. Non-smoking, pet-free. Minisplit for AC/heat, Smart TV and WiFi. Plenty of parking for vehicles/boat.

Guest favourite
A modern river cabin is pictured from the front, featuring a metal roof, wood siding, and a spacious porch with a railing. A gravel driveway leads up to the attached garage, surrounded by grassy areas and trees, under a cloudy sky.
Cabin in Platte
4.93 out of 5 average rating, 56 reviews

Twin Pine River House

Relax with the whole family at this peaceful river cabin. Located on the Missouri River hills near Platte Creek Recreation Area near Platte, SD. Enjoy all this area has to offer: fishing, boating, beaches, hiking, pheasant hunting, deer hunting, turkey hunting, ice fishing. Newly finished garage with air conditioning and heat, very pet friendly. Looking to relax, enjoy the beautiful sunrises on the front porch or sunsets on the back deck.

Top Guest favourite
The living room is arranged with two cozy sofas in various sizes, complemented by decorative cushions. A neutral-toned area rug is placed on the floor, and a flat-screen TV is mounted on the wall. Natural light enters through the window, adorned with simple curtains.
Guesthouse in Winner
4.99 out of 5 average rating, 74 reviews

The Rustic MP6

Relax with the whole family at this peaceful place to stay. two bedrooms one queen bed other full bed. the living room has two sofas with beds in them. they are full size and queen size beds. Just recently added two rollaway beds (twin size) can host up to 5-10 people if you don't mind sharing a bed. no smoking or no pets inside. beautiful view!

Guest favourite
A charming farmhouse exterior is framed by tall trees and a white picket fence. The house features a pitched roof and a porch with large windows, inviting natural light. Grass surrounds the property, creating a serene rural setting.
Home in Winner
4.95 out of 5 average rating, 103 reviews

Grandma’s House - peaceful, 28 miles to Niobrara

Enjoy the peace and quiet of this quaint old farmhouse on a working farm/ranch in the country, 28 miles to Niobrara River in Nebraska, 26 miles to Sparks, for tubing and canoeing, 45 miles to Valentine, Nebraska, 28 miles from Winner, SD. Ask about a camper hookup, outdoor arena for riding, weather permitting, and pens for your horses.

Top Guest favourite
A spacious living area showcases a mix of comfortable seating and a dining space that accommodates six. Natural wood accents offer a warm ambiance, complemented by decorative wall-mounted animal mounts. The open layout includes a well-equipped kitchen, enhancing the inviting setting.
Home in Chamberlain
4.99 out of 5 average rating, 171 reviews

Racquet on Elm Street

Welcome to Racquet on Elm St. Situated in a quiet neighborhood just minutes from the Missouri River/Lake Francis Case, this lodge-style home is designed for comfort, relaxation and fun. This spacious 3BR/2.5BA home, spanning over 2,400 square feet, was completed in April 2019 and includes its very own private attached racquetball court.

Top Guest favourite
A cozy sitting area is highlighted by a plush sofa adorned with decorative pillows. A small round table is positioned in front, complemented by a patterned area rug. Wall accents include framed artwork and stylish light fixtures that add a warm glow.
Guest suite in Winner
4.94 out of 5 average rating, 161 reviews

The Hide-A-Way

Have fun in the heart of pheasant country on the east edge of Winner, South Dakota. This newly remodeled space has been converted from an old lumber yard into a homey and comfortable space. It's less than a mile from town and is conveniently located on Us Highway 18. Within walking distance to the drive-in theater and local museum.

Top Guest favourite
The exterior of the cabin is presented, featuring a spacious design with a green roof and light-colored siding. A covered porch extends across the front, offering shade. Tall pine trees are visible in the foreground, adding to the natural setting, under a clear blue sky.
Cabin in Sparks
5 out of 5 average rating, 18 reviews

Muleshoe Creek Guesthouse overlooking the Niobrara

Take it easy at this unique and tranquil getaway. Overlooking the Niobrara River Valley you are minutes away from floating the Niobrara National Scenic River, exploring Smith Falls, hitting up a Norden dance, or golfing one of the many golf courses in north central Nebraska. These are just a few of the adventures that await.

Popular amenities for Winner holiday rentals

  1. Airbnb
  2. United States
  3. South Dakota
  4. Tripp County
  5. Winner