Holiday rentals in Winner

The Log Cabin

Log cabin just minutes away from the Missouri River, public beach, marina & airport. Plenty of indoor & outdoor space for entertaining. Perfect for family gatherings, fishing & hunting trips. This three-story cabin sleeps up to 15, includes 5 bedrooms, 10 beds, 2 folding beds & 3 bathrooms. Fully loaded kitchen with plenty of seating, front/rear decks and walkout basement. Large loft. Garage game room with mini pool table & foosball. Blackstone Griddle, large yard, swing set & playhouse.

Location · Family · TV

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.

Value · Location · Air conditioning

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.

Family · Location · Hospitality

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.

Location · Value · Quiet

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!

Location · Family · Nearby

N1- Spacious Cottage Getaway |Sleep 8 |Near Dining

The Cottages feature two identical, well-appointed rental units, each sleeping up to 8 guests—ideal for families, friends, or group stays. Enjoy a comfortable, hassle-free visit with all bedding, towels, and home essentials provided. Located just 4 miles west of Gregory, close to local favorites like Frank’s Days and Runors Fine Dining. Units may be booked individually or together. Stay a full week and receive one complimentary night!

Location · Family · Hospitality

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.

Location · Family · Bathroom

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!

Family · Location · Condition

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.

Value · Location · Access

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.

Location · Family · Indoor spaces

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.

Family · Location · Check-in

The Quiet House

Country living, 3 miles from town. Quiet, peaceful, sit out on the covered deck, look at the stars! Surrounded by open spaces….Basketball hoops and a big yard to enjoy!! Pets are welcome!!

Location · Family · Quiet