
Holiday houses in Winner
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Top-rated holiday rentals in Winner
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Chamberlain 2 Bdrm Cabin, with Man Cave, sleep 4-6
2 bedroom cabin connected to the heated man cave includes a kitchen, dining table, microwave, sink, refrig, oven; 1 bedroom with queen bed, 1 bedroom with bunk beds , a pull-out sofa in living room, and full bathroom. Washer & dryer available. Large gravel parking lot pull thru Cabin sits on 3-acre lot with wildlife, impeccable views of Missouri River and the sunset. The property is quiet, away from crowds, offers easy access from Hwy 50, Close to American Creek Marina, downtown Chamberlain

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.

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.

Where the Wild Things Are
Come visit our house just north of the Niobrara River in the little community of Springview, NE. Where the wild things run - around here you can find antelope, elk, whitetail deer, mule deer and so much more. We offer three bedrooms and two bathrooms, washer/dryer, full kitchen with the necessary cooking utensils, grill, heat/AC, and your own TV in every room. We are finishing up a remodel winter 2024. Family Friendly. Come visit and see all of what northern Nebraska has to offer.

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.

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!

Sportsman Overlook of the Missouri River
Single story walkout Rags supplied for those messes and spills. Towels, wash cloths, bedding, dishes, pots & pans are provided. New mattresses installed 2022 Whirlpool bathtub in MB So your next visit should be a bit more comfy than the previous visit!! NOTE: There are several types of snakes native to the area. Bull, racer and rattlesnake. We have seen all of these in the past ten years.

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.

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.

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.
Popular amenities for Winner holiday rentals
Other great holiday rentals in Winner

Single queen room #1. Brand new construction!

Mabel's apartment

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Robbins Retreats S.A. House

Maggie’s Place

2 bdrm, 3 bed, fncd pvt yard, no pet fee!

Retro Chic Getaway

The Boar's Tusk Lodge




