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.

Guest favourite
Home in Presho
Presho Prairie Paradise
Located on the prairie just off I-90, this newly remodeled home is ideal for the cross country travelers on your way to or from the Black Hills or your group coming for prime pheasant hunting. Gather around the large kitchen island playing games or reminiscing about your trip. Large deck off the kitchen for grilling or just enjoying the outdoors. House has open floor plan where you can relax in front of the fireplace and still be part of the conversation.
Jan. 15 – 22
$388 CAD per night
4.99 out of 5 average rating, 192 reviews
Guest favourite
Home in Valentine
Kate’s Place
Our home is located in a safe, quiet neighborhood on the northwest edge of the “Heart City” in the beautiful Sandhills of Nebraska. Deer often scale the chain link fence in our backyard for a snack when the apples ripen. Enjoy the small hometown, friendly atmosphere of Valentine. Downtown, just eight blocks away, you’ll find several quaint and unique shops featuring locally produced and crafted items.
Aug. 16 – 23
$202 CAD per night
4.96 out of 5 average rating, 124 reviews
Guest favourite
Guesthouse in Winner
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.
May 13 – 20
$159 CAD per night
4.97 out of 5 average rating, 107 reviews

Popular amenities for Winner vacation rentals

Other great vacation rentals in Winner

Guest favourite
Home in Winner
Grandma’s House - peaceful, 28 miles to Niobrara
Jul. 17 – 24
$112 CAD per night
4.97 out of 5 average rating, 75 reviews
Superhost
Home in Dallas
Sweet Home Dallas South Dakota
Mar. 3 – 10
$171 CAD per night
4.68 out of 5 average rating, 19 reviews
Guest favourite
Home in Gregory
Cozy 4 bedroom farm house
Sep. 30 – Oct. 7
$220 CAD per night
4.85 out of 5 average rating, 47 reviews
Guest favourite
Home in Valentine
Sharptail Lodge
Dec. 8 – 15
$377 CAD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Cabin in Chamberlain
Log Cabin
Nov. 25 – Dec. 2
$578 CAD per night
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Gregory
Peaceful and Fully Upgraded: 4 Bedroom House
Jan. 30 – Feb. 6
$500 CAD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Townhouse in Pukwana
1 Bedroom, fenced in pvt yard, no pet fee!
Jan. 22 – 29
$239 CAD per night
4.98 out of 5 average rating, 48 reviews
Guest favourite
Cabin in Chamberlain
Chamberlain 2 Bdrm Cabin, with Man Cave, sleep 4-6
Jan. 13 – 20
$301 CAD per night
4.96 out of 5 average rating, 54 reviews
Guest favourite
Home in Oacoma
Sunset River View
Apr. 5 – 12
$656 CAD per night
4.98 out of 5 average rating, 44 reviews
Guest favourite
Home in Chamberlain
American Creek Retreat
Mar. 28 – Apr. 4
$522 CAD per night
4.93 out of 5 average rating, 14 reviews
Guest favourite
Home in Valentine
Valentine’s Tourist Tenure— No Cleaning Fee!
Oct. 5 – 12
$308 CAD per night
4.95 out of 5 average rating, 20 reviews
Superhost
Home in Valentine
Valentine Vacation Rental w/ Modern Interior!
Dec. 24 – 31
$473 CAD per night
4.67 out of 5 average rating, 3 reviews

Quick stats about vacation rentals in Winner

Total rentals

10 properties

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Pet-friendly rentals

10 properties allow pets

Total number of reviews

110 reviews

Nightly prices starting at

$54 CAD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. South Dakota
  4. Tripp County
  5. Winner