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.

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.

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.

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.

Prairie View Cottage

INTERIOR HAS CHANGED. UPDATED PICTURES COMING SOON. Locally owned and operated! Take a break and unwind at this peaceful oasis. Discover the perfect blend of comfort style and the great outdoors at our one bedroom, one bathroom cottage near Valentine. Ideal for adventurers, our home offers a distinctive experience with its large yard space, beautiful sunsets, and abundant wildlife. Experience the convenience of high-speed Wi-Fi, smart TV, air conditioning, and other modern amenities.

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.

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.

Retro Chic Getaway

What do you get when the ’70s and ’90s have a love child? This apartment. Just off Main St in Winner, SD, this 2-bedroom throwback delivers bold vibes with all the essentials. It’s clean, affordable, and perched above a local tech company (tech troubles? Yep—we know a guy). You’ll be steps from restaurants, bars, and—shameless plug—one of the best tattoo shops in the Midwest. Step inside, soak up the patterns, and let nostalgia run wild. Welcome to your vintage getaway!

Welcome to our cozy escape "The Bunkhouse"

Discover your perfect rural retreat in our charming and cozy bunkhouse. Surrounded by the gentle rhythm of farm life and the natural beauty of the open fields. This rustic escape offers a truly peaceful setting to unwind and recharge. Gaze out over endless farm fields, breathe in the fresh country air, and let the quiet, starlit nights wash your worries away.

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!

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.