Vacation rentals in Winner

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Top-rated vacation rentals in Winner

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Top guest favorite
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, 64 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.

Top guest favorite
The exterior of the house features a modern design with a high-pitched roof and large windows. A covered deck with railing extends from the front, providing access to outdoor seating. The surrounding area includes open space with a gravel driveway leading up to the entrance.
Home in Gregory
5 out of 5 average rating, 27 reviews

Home with a View - Running Horse Guest House

This property was originally designed to serve as a hunting lodge and our second home. There are 3 smaller bedrooms and one larger master bedroom. Each bedroom has a private bath, the master having a large whirlpool tub. Focus is on the common areas. There is a widescreen TV with Direct TV service, free high speed internet, a large fireplace, and a well equipped kitchen. The kitchen includes a 5-burner cook top, a double convection oven, microwave, refrigerator, freezer and dishwasher.

A lively common area showcases vintage decor and unique local signs. A bar area is illuminated by a neon beer sign, while various framed pictures and posters adorn the wooden walls. The space is complemented by a mix of seating options, inviting guests to relax and socialize.
Home in Colome
5 out of 5 average rating, 3 reviews

Sign Inn Colome

Welcome to the Sign Inn located on Main Street Colome, South Dakota. Take a step back in time and enjoy the eclectic style of the Sign Inn, which is fully decorated with vintage items and it’s signature local signs, many of which has local roots to the central South Dakota area. Each room and area of the Sign Inn has been curated to tell a story while also providing an updated and comfortable stay to guests. We welcome all guests - hunters and travelers to join us at the Sign Inn.

Guest favorite
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.

Guest favorite
A two-story home presents a welcoming facade with a blue exterior. The front yard is landscaped with greenery and flower beds. A front porch with steps leading up to the entrance creates an inviting space. A spacious driveway is visible on the side.
Home in Chamberlain
5 out of 5 average rating, 11 reviews

Riverview Whole House Rental 9 rooms sleeps 22

Riverview property! 9 Bedrooms, 8 Baths sleep 22 comfortably 2 Living rooms fully equipped kitchen, deck w/ gas fire pit outdoor seating, large yard overlooking the Missouri River! You don't want to miss this view! Spacious home for everyone & your pets! Pet ONLY rooms #6-7-8-9. Perfect for your reunions, weddings, and special events! We are located in a residential area. Very quiet and peaceful here. We are located 1 mile from downtown. Beautiful sunsets over the Missouri river

Top guest favorite
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 bunks (4 twins) in bedroom #2. Sleeps up to 6.

Top guest favorite
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, 70 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 a rollaway bed (twin size) can host up to 5-9 people if you don't mind sharing a bed. no smoking or no pets inside. beautiful view!

Guest favorite
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 favorite
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, 167 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 favorite
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, 158 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.

A rustic exterior of a wooden cabin showcases a blend of natural wood and green siding. A flagpole stands prominently in front, with a flag gently waving. Surrounding greenery includes trees and well-kept grass, enhancing the peaceful rural setting.
Cabin in Dallas
4.71 out of 5 average rating, 42 reviews

The Ranch

A little piece of heaven centered right in the heart of pheasant country. This property can house up to 16 people if needed and is very quit and secluded. It sets on a 160 acres of rural property. This site is great for larger family's that like to be outside and there is plenty of room for parking any sized vehicles.

Home in Winner
5 out of 5 average rating, 3 reviews

The Nelson House

3 bedroom home with room for the whole family. Stocked with everything you would need for your stay. Spacious garage, great for parking your car or processing wild game. *if calendar does not have availability for your selected dates, please reach out to me directly*

Popular amenities for Winner vacation rentals

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