Vacation rentals in Winner

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!

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.

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.

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.

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.

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.