Winner, SD

Travel Guide

Aerial View of Sturgis, South Dakota Which hosts an annual Motorcycle Rally
Aerial View of Winner, South Dakota in Winter
Winner
Holiday Inn Express & Suites Winner by IHG

Holiday Inn Express & Suites Winner by IHG

2.5 out of 5
1360 E Highway 44 Winner SD
The price is SAR 443 per night from May 17 to May 18
SAR 443
per night
May 17 - May 18
Book a stay at this business-friendly hotel in Winner. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (358 reviews)
We got in at 9 o’clock that night and got up at 5:30 the next morning to go turkey hunt so I really didn’t get to experience a lot

Reviewed on 19 April 2026

Holiday Inn Express & Suites Winner by IHG
Super 8 by Wyndham Winner SD

Super 8 by Wyndham Winner SD

2 out of 5
902 E Highway 44 Winner SD
The price is SAR 290 per night from May 13 to May 14
SAR 290
per night
May 13 - May 14
Stay at this motel in Winner. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tripp County Veteran’s Memorial and Winner City Pool are ...
7.8/10 Good! (330 reviews)
Room was clean and inviting. We didnt stay for breakfast as this was just a quick stay.

Reviewed on 21 April 2026

Super 8 by Wyndham Winner SD
Warrior INN

Warrior INN

2 out of 5
845 SD-44 Winner SD
The price is SAR 264 per night from Jun 7 to Jun 8
SAR 264
per night
Jun 7 - Jun 8
Stay at this motel in Winner. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Tripp County Veteran’s Memorial and Winner City Pool ...
6/10 (10 reviews)
Room was clean. Very cold. Had the heat turned up as far as it would go. Laminate floors cold too. Tv quit working. Outside security doors unlocked. No coffee machine or iron. Pretty basic.

Reviewed on 25 January 2026

Warrior INN
See all 29 properties in Winner
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Cozy Little Getaway, Winner, SD

Cozy Little Getaway, Winner, SD

Winner SD
Stay at this vacation home in Winner. Enjoy laundry facilities, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Winner Bass Pond ...
10/10 Exceptional! (12 reviews)
Check in and spacious clean house.

Reviewed on 14 November 2025

Cozy Little Getaway, Winner, SD
Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home

Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home

Valentine NE
Stay at this vacation home in Valentine. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Cherry County Historical Society Museum and Bryan ...
10/10 Exceptional! (3 reviews)
Cozy place! Walking distance to many things.

Reviewed on 20 August 2025

Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home
Centrally located spacious house in Valentine, 4 bedrooms, 5 beds, sleeps 8

Centrally located spacious house in Valentine, 4 bedrooms, 5 beds, sleeps 8

Valentine NE
Stay at this vacation home in Valentine. Enjoy a garden, laundry facilities, and patios. Popular attractions Trailhead Park and Cherry County Historical Society ...
8.8/10 Excellent! (3 reviews)
Cindy was awesome ! Answered questions very properly. House had plenty of space Thank you, Cindy.

Reviewed on 23 November 2025

Centrally located spacious house in Valentine, 4 bedrooms, 5 beds, sleeps 8
See all properties in Winner
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

A golfer about to putt with flag in the background

Winner Country Club

Enjoy a round of golf in Winner at Winner Country Club. Make time to visit the churches and monuments while you're in the area.

Winner Country Club

Tripp County Veteran’s Memorial

You can find out about the history of Winner with a stop at Tripp County Veteran’s Memorial. Make time to visit the monuments and churches while you're in the area.

Tripp County Veteran’s Memorial

Winner City Park

After visiting Winner City Park, make a plan to see the other sights and activities in Winner. Make time to visit the churches and monuments while you're in the area.

Winner City Park

Winner Bass Pond

After visiting Winner Bass Pond, make a plan to see the other sights and activities in Winner. Make time to visit the churches and monuments while you're in the area.

Winner Bass Pond

Winner City Pool

You can take time to visit Winner City Pool during your travels to Winner. Make time to visit the churches and monuments while you're in the area.

Winner City Pool

Bailey's Park

Bailey's Park is just one of the places to see in Winner, so why not enjoy the other things to explore during your travels? Make time to visit the churches and monuments while you're in the area.

Bailey's Park