Winner

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 CA $161 per night from May 17 to May 18
CA $161
CA $175 total
May 17 - May 18
includes taxes & fees
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 Apr 19, 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 CA $100 per night from May 18 to May 19
CA $100
CA $109 total
May 18 - May 19
includes taxes & fees
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 Apr 21, 2026

Super 8 by Wyndham Winner SD
Cozy Little Getaway, Winner, SD

Cozy Little Getaway, Winner, SD

Winner SD
The price is CA $150 per night from May 14 to May 15
CA $150
CA $224 total
May 14 - May 15
includes taxes & fees
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 Nov 14, 2025

Cozy Little Getaway, Winner, SD
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 Nov 14, 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 Aug 20, 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 Nov 23, 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

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

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 Regional Healthcare Center

Though Winner Regional Healthcare Center might be what brings you to town, perhaps you'll have a chance to explore more of Winner while you are here.

Winner Regional Healthcare Center