Holiday rentals in Winner

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.

River Shore Rentals

Gorgeous views of the Missouri River from the HUGE front porch!! The lodge can host up to 16 people with plenty of living and outdoor space to enjoy your stay. 4 bedrooms, 8 beds, 2 full baths and a beautiful, fully supplied kitchen and dining for 8. Great place for family gatherings, hunting, or fishing!! The lodge sits right across the street from the Cedar Shore Marina and boat ramp. There is a bike path across the street that extends for miles for you to enjoy views of the Missouri River.

Valentine’s Tourist Tenure

Valentine’s Tourist Tenure is Located right off HWY 97 on your way to Merritt Dam. We would love to host you during your time in the Heart City! Our cozy little space has all that you will need for time away and we aim to make you to feel right at home. It is located close to the Bait shop and all of the restaurants, gas stations, Scotty’s Ranchland Foods, and more. There is plenty of room on the property for parking your RV, trailer, or boat as well. We can’t wait to host you for you stay!

Retro vibes & funky soul inside!

A vibey vintage haven where mid-century charm meets modern flair. Think bold colors, disco-ball energy, and plants that party harder than the guests. Every corner’s got a story — from the velvet couch that’s seen more gossip than a high school hallway, to the kitchen that moonlights as a late-night taco lab. It’s cozy, it’s quirky, it’s got soul — welcome to the spot where good vibes live rent-free.

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!

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.

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.

Spacious Duplex Getaway

Bring the whole family to this great place with lots of room for fun. Great screened in porch for evening sitting, family games including a foosball table. Full kitchen, washer & dryer, smart tv, and fireplace. The Co-Host live on the other side. The duplex is located only 15 miles from the Missouri River.

Borg Guest House

The Borg BNB is a 2 bedrooms/1bath allowing to sleep up to 8 guests with a sleeper sofa. A walk in shower, full kitchen, and laundry room are highlights of the home but the open concept makes this space ideal to gather around the table and enjoy everyone’s company.