Vacation rentals in Winner

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Top-rated vacation rentals in Winner

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Superhost

Home in Chamberlain

5 out of 5 average rating, 7 reviews

Riverview Whole House Rental

Riverview property! 9 Bedrooms, 8 Baths sleep 24 comfortably 2 Living rooms fully equipped kitchen, deck w/ gas fire pit outdoor seating, large yard overlooking the Missouri River! You don't want to miss this view! Spacious home for everyone & your pets! Perfect for your reunions, weddings, and special events! We are located in a residential area. Very quiet and peaceful here. We are located 1 mile from downtown. You have a beautiful view of the Missouri River, sit, relax, and watch the sunset.

Guest favorite

Cabin in Chamberlain

5 out of 5 average rating, 39 reviews

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.

Guest favorite

Home in Gregory

5 out of 5 average rating, 15 reviews

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.

Guest favorite

Home in Colome

4.92 out of 5 average rating, 13 reviews

3 bed Hunter/Cowboy Bunk house in Country

Book this for your family/hunting trip! Older simple house with 3 beds, a couch hide-a-bed, w enough room in one bedroom to add an air mattress. 1 bathroom. Full Kitchen with stove, fridge, micro & dishes. Window AC. Large yard. We even have pens for your horses/cattle and an indoor arena to ride in for additional fees. Dogs welcome but must be kenneled outside. NO smoking. If you want new & fancy, this place is not for you. We offer clean beds in a great rural setting.

Guest favorite

Home in Winner

4.94 out of 5 average rating, 67 reviews

Cozy Little Getaway

*if calendar does not show availability for your desired dates please direct message me regarding availability - or book through this website directly that has updated calendar https://cozylittlegetaway.lodgify. com (remove the space between . and com to get link to work) 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 and everything you may need for your stay.

Guest favorite

Guesthouse in Winner

4.97 out of 5 average rating, 124 reviews

Glory Be on the Prairie

Ten miles west of Winner, South Dakota, in the country on Highway 18. Private, shady location among the pines and trees with a view of the ‘Carter Hills’ to the West. Direct link from East to the West by using Highways 183 to interstate 90, Highway 44 to the Badlands and Rapid City or Highway 18 through the Rosebud and Pine Ridge Reservation to Custer State Park and Hot Springs.

Guest favorite

Home in Gregory

4.94 out of 5 average rating, 17 reviews

Peaceful and Fully Upgraded: 4 Bedroom w/ 4 Beds

This has 4 beds and 3 bathrooms. Whether you are here for family, fishing or hunting, there is plenty of room for parking your vehicles and boats. Enjoy cooking or grilling out in the fully stocked kitchen with a over sized island for even more entertaining space. After a long day of fun, nestle into the top-notch adjustable beds that are awaiting you.

Guest favorite

Guesthouse in Winner

4.97 out of 5 average rating, 34 reviews

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!

Guest favorite

Guest suite in Winner

4.94 out of 5 average rating, 118 reviews

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.

Guest favorite

Home in Gregory

4.88 out of 5 average rating, 56 reviews

Cozy 4 bedroom farm house

Relaxing place for the family, and in the center of pheasant and deer hunting! Out in the country!! 3 miles from Gregory! If you are looking for a peaceful and relaxing place to stay, please consider this place, we try hard to make everything as convenient and comfortable as possible!!