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 14 to May 15
SAR 443
SAR 481 total
14 May - 15 May
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. ...
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 255 per night from Apr 22 to Apr 23
SAR 255
SAR 277 total
22 Apr - 23 Apr
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! (327 reviews)
Staff is great!

Reviewed on 25 March 2026

Super 8 by Wyndham Winner SD
Warrior INN

Warrior INN

2 out of 5
845 SD-44 Winner SD
Fully refundable
The price is SAR 269 per night from Apr 23 to Apr 24
SAR 269
SAR 292 total
23 Apr - 24 Apr
includes taxes & fees
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 28 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
Rustic Ridge

Rustic Ridge

Gregory SD
Stay at this vacation home in Gregory. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker.
9.6/10 Exceptional! (5 reviews)
Every thing was great

Reviewed on 15 November 2025

Rustic Ridge
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
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 Regional Hospital

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

Winner Regional Hospital

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 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 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