Book Holiday Homes in Winner

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Featured Holiday Homes in Winner

Rustic Ridge

Rustic Ridge

Gregory
When you stay at this vacation home in Gregory, you'll be 7 minutes by car from Avera Gregory Hospital.
Rustic Ridge
Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home

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

Valentine
With a stay at this vacation home in Valentine, you'll be within a 10-minute walk of Cherry County Historical Society Museum and Bryan Bridge.
Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home
Cozy Little Getaway, Winner, SD

Cozy Little Getaway, Winner, SD

Winner
With a stay at this vacation home in Winner, you'll be within a 10-minute walk of Winner City Park and McDonald's Park.
Cozy Little Getaway, Winner, SD
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Cherry Street Cottage is a nice 2-bedroom house in Valentine that has it all.

Cherry Street Cottage is a nice 2-bedroom house in Valentine that has it all.

Valentine
Located in Valentine, this vacation home is within a 15-minute walk of Trailhead Park and Niobrara National Scenic River Headquarters.
Cherry Street Cottage is a nice 2-bedroom house in Valentine that has it all.
The Ranch You Love

The Ranch You Love

Dallas
With a stay at this vacation home in Dallas, you'll be 10.5 mi (16.9 km) from Avera Gregory Hospital and 15.3 mi (24.7 km) from Beaulieu Lake.
The Ranch You Love
Charming 3-bedroom house in peaceful Valentine with everything you’ll need.

Charming 3-bedroom house in peaceful Valentine with everything you’ll need.

Valentine
Located in Valentine, Charming 3-bedroom house in peaceful Valentine with everything you’ll need. is within a 15-minute walk of Trailhead Park and Niobrara National ...
Charming 3-bedroom house in peaceful Valentine with everything you’ll need.
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
With a stay at this property in Valentine, you'll be within a 10-minute walk of Trailhead Park and Niobrara National Scenic River Headquarters.
Centrally located spacious house in Valentine, 4 bedrooms, 5 beds, sleeps 8
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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.

Winner Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winner vacation homes are the perfect way for you to wing it.

Holiday houses in Winner let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winner in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winner adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winner with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winner vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winner Holiday Homes essential information

Accommodation
5 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Rustic Ridge, Valentine’s Tourist Tenure- Charming 2 bedroom cozy vacation home, Cozy Little Getaway, Winner, SD, Cherry Street Cottage is a nice 2-bedroom house in Valentine that has it all., The Ranch You Love, Charming 3-bedroom house in peaceful Valentine with everything you’ll need., Centrally located spacious house in Valentine, 4 bedrooms, 5 beds, sleeps 8

Top trending hotels in 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
Fully refundable
Located in Winner, Holiday Inn Express & Suites Winner by IHG is in a rural location, within a 5-minute drive of Tripp County Veteran’s Memorial and Winner Regional ...
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
Fully refundableReserve now, pay when you stay
Located in Winner, Super 8 by Wyndham Winner SD is in a rural location, within a 5-minute drive of Tripp County Veteran’s Memorial and Winner Regional ...
Super 8 by Wyndham Winner SD
Knights Inn Winner

Knights Inn Winner

1.5 out of 5
845 E. Highway 44, Winner, SD
A stay at Knights Inn Winner places you in the heart of Winner, within a 15-minute walk of Tripp County Veteran’s Memorial and Winner Regional Hospital.
Knights Inn Winner
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Cozy Little Getaway, Winner, SD

Cozy Little Getaway, Winner, SD

Winner
With a stay at this vacation home in Winner, you'll be within a 10-minute walk of Winner City Park and McDonald's Park.
Cozy Little Getaway, Winner, SD
Don't see what you're looking for?
See all available properties in Winner
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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.

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^Subject to availability and chosen travel dates.