Holiday rentals 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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Top guest favourite
The living area features a high, vaulted ceiling with wood paneling and large windows that allow natural light to fill the space. A stone fireplace serves as the focal point, complemented by two black sofas and a central coffee table, creating a cozy gathering spot.
Cabin in Chamberlain
5 out of 5 average rating, 63 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 favourite
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, 25 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 favourite
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, 10 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 favourite
A living area features two comfortable sofas, complemented by decorative pillows. A round table with a plant is set beside a chair. Natural light enters through the window, highlighting the wood flooring and a wall clock, contributing to a cozy ambiance.
Home in Chamberlain
4.95 out of 5 average rating, 55 reviews

American Creek Retreat

Just a block from the Missouri River and walking distance to boat ramps at American Creek Marina.. it’s a 7 bedroom (14 beds) 3 bath home, with large dining room for gathering, full kitchen featuring double oven range and coffee bar, additional upstairs living room and kitchenette bar area, large mudroom for all of your outdoor adventure equipment, and a separate “poker room” / party room and so much more!

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, 6 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 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.
Guest house in Winner
4.99 out of 5 average rating, 68 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 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, 99 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, 163 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
4.95 out of 5 average rating, 154 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.

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*

Top guest favourite
A stone pathway leads through a manicured yard towards a wooden duplex with a welcoming entrance. An in-ground firepit is positioned at the forefront, surrounded by gravel and bordered by landscaped grass. Fencing provides privacy while enhancing the outdoor space.
Townhouse in Pukwana
4.97 out of 5 average rating, 65 reviews

1 Bedroom, fenced in pvt yard, no pet fee!

Cozy, rustic feel duplex built in 2016, quiet neighborhood, large parking area, fully furnished, washer/dryer, electric fireplace, AC, kitchen appliances, cookware, and more. In-ground firepit, patio, 10 minutes to Chamberlain. This unit is downstairs.

Popular amenities for Winner holiday rentals

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