183+ Private Villas and Holiday Rentals in Winner |
Winner Holiday Rentals
House
- South Dakota
- ·
- Chamberlain
- 0.72 mi to center
10.0Exceptional
(42 Reviews)
3 Bedrooms
1 Bath
5 Guests
Fireplace/Heating
Balcony/Terrace
Kitchen
Parking
US $267/Night
7 Nights - US $1,871
Apartment
- South Dakota
- ·
- Winner
- 8.97 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
7 Guests
Pet Friendly- Parking
Air Conditioner
Internet
US $110/Night
7 Nights - US $767
Cabin
- Chamberlain
- ·
- Kimball
- 8.63 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
Spa- Fireplace/Heating
Pool- Balcony/Terrace
US $159/Night
7 Nights - US $1,110
House
- South Dakota
- ·
- Chamberlain
- 0.75 mi to center
10.0Exceptional
(41 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $246/Night
7 Nights - US $1,725
House
- South Dakota
- ·
- Winner
- 8.87 mi to center
9.2Exceptional
(6 Reviews)
5 Bedrooms
1 Bath
8 Guests
301.39 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $120/Night
7 Nights - US $840
House
- South Dakota
- ·
- Pukwana
- 1.46 mi to center
10.0Exceptional
(23 Reviews)
2 Bedrooms
1 Bath
5 Guests
880 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $200/Night
7 Nights - US $1,401
Apartment
- Chamberlain
- ·
- Platte
- 6.88 mi to center
10.0Exceptional
(7 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $182/Night
7 Nights - US $1,272
House
- South Dakota
- ·
- Pukwana
- 1.37 mi to center
9.8Exceptional
(10 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $184/Night
7 Nights - US $1,288
Cabin
- South Dakota
- ·
- Brule County
- 3.11 mi to center
9.6Exceptional
(64 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $126/Night
7 Nights - US $880
Luxury Holiday Rentals in Winner
Over 174+ Luxury Holiday Rentals in or Near Winner
House
- South Dakota
- ·
- Chamberlain
- 1.29 mi to center
9.6Exceptional
(25 Reviews)
5 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $719/Night
7 Nights - US $5,031
Cabin
5 Bedrooms
2 Baths
15 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $719/Night
7 Nights - US $5,030
House
- South Dakota
- ·
- Chamberlain
- 1.49 mi to center
10.0Exceptional
(21 Reviews)
4 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $688/Night
7 Nights - US $4,819
Cabin
3 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $617/Night
7 Nights - US $4,322
House
- Chamberlain
- ·
- Oacoma
- 0.93 mi to center
9.6Exceptional
(14 Reviews)
5 Bedrooms
3 Baths
17 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $580/Night
7 Nights - US $4,057
Cabin
- South Dakota
- ·
- Chamberlain
- 4.38 mi to center
10.0Exceptional
(83 Reviews)
5 Bedrooms
3 Baths
15 Guests
Hot Tub- Fireplace/Heating
Ocean View- Balcony/Terrace
US $577/Night
7 Nights - US $4,038
Cabin
- South Dakota
- ·
- Winner
- 9.32 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $536/Night
7 Nights - US $3,750
House
- South Dakota
- ·
- Fairfax
- 0.82 mi to center
9.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
9 Guests
3003.13 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $532/Night
7 Nights - US $3,726
House
- South Dakota
- ·
- Chamberlain
- 4.05 mi to center
9.8Exceptional
(106 Reviews)
7 Bedrooms
1 Bath
18 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $518/Night
7 Nights - US $3,626
Top-Rated Holiday Rentals with a Pool in Winner
Over 49+ The Best Private Villas and Holiday Rentals in Winner with a Pool
Cabin
- Chamberlain
- ·
- Platte
- 8.73 mi to center
10.0Exceptional
(30 Reviews)
3 Bedrooms
3 Baths
12 Guests
1700 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $450/Night
7 Nights - US $3,148
Cabin
- Chamberlain
- ·
- Kimball
- 4.93 mi to center
10.0Exceptional
(3 Reviews)
10 Bedrooms
14 Baths
40 Guests
10000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $123/Night
7 Nights - US $862
Hotel
- South Dakota
- ·
- Murdo
- 4.99 mi to center
9.0Exceptional
(785 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Balcony/Terrace
US $148/Night
7 Nights - US $1,035
Hotel
- Chamberlain
- ·
- Oacoma
- 0.82 mi to center
8.8Fabulous
(1002 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
Breakfast
US $131/Night
7 Nights - US $920
Hotel
- South Dakota
- ·
- Winner
- 9.52 mi to center
8.8Fabulous
(355 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $124/Night
7 Nights - US $867
Hotel
- South Dakota
- ·
- Chamberlain
- 2.69 mi to center
8.6Fabulous
(1003 Reviews)
1 Bath
- Hot Tub
- Fireplace/Heating
- Pool
- Breakfast
US $116/Night
7 Nights - US $809
Hotel
- Chamberlain
- ·
- Oacoma
- 0.36 mi to center
8.6Fabulous
(1003 Reviews)
1 Bath
- Hot Tub
- Pool
- Breakfast
- Pet Friendly
US $94/Night
7 Nights - US $658
Hotel
- Chamberlain
- ·
- Oacoma
- 0.34 mi to center
8.6Fabulous
(821 Reviews)
7 Baths
432.1 ft²
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $136/Night
7 Nights - US $950
Hotel
- South Dakota
- ·
- Murdo
- 4.96 mi to center
8.6Fabulous
(533 Reviews)
3 Baths
290.63 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $130/Night
7 Nights - US $910
Pet-Friendly Holiday Rentals in Winner
Over 58+ Pet-Friendly Holiday Rentals in or Near Winner
House
- Chamberlain
- ·
- Platte
- 9.15 mi to center
9.4Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
8 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Internet
US $301/Night
7 Nights - US $2,106
Resort
- South Dakota
- ·
- Chamberlain
- 1.44 mi to center
8.4Excellent
(168 Reviews)
4 Baths
60 Guests
410.46 ft²
- Private Pool
Oceanfront- Hot Tub
- Fireplace/Heating
US $216/Night
7 Nights - US $1,514
RV Rental
- Chamberlain
- ·
- Platte
- 8.90 mi to center
9.2Exceptional
(17 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $203/Night
7 Nights - US $1,424
Cabin
7.9Very Good
(72 Reviews)
57 Bedrooms
1 Bath
19 Guests
312.15 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $169/Night
7 Nights - US $1,183
Cabin
- South Dakota
- ·
- Brule County
- 3.04 mi to center
9.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Child Friendly
US $106/Night
7 Nights - US $740
Cabin
- Chamberlain
- ·
- Platte
- 5.85 mi to center
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
View
US $316/Night
7 Nights - US $2,215
House
- Chamberlain
- ·
- Platte
- 7.33 mi to center
8.0Excellent
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $179/Night
7 Nights - US $1,250
House
- Chamberlain
- ·
- Platte
- 6.97 mi to center
10.0Exceptional
(58 Reviews)
3 Bedrooms
1 Bath
6 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $194/Night
7 Nights - US $1,357
House
- Chamberlain
- ·
- Platte
- 6.99 mi to center
10.0Exceptional
(26 Reviews)
3 Bedrooms
1 Bath
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $173/Night
7 Nights - US $1,210
Large Holiday Rentals and Private Villas in Winner
Over 31+ Large Holiday Rentals and Private Villas in or Near Winner
Cabin
- South Dakota
- ·
- Chamberlain
- 4.18 mi to center
10.0Exceptional
(21 Reviews)
6 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $378/Night
7 Nights - US $2,645
Cabin
- Chamberlain
- ·
- Oacoma
- 0.45 mi to center
7.3Very Good
(54 Reviews)
43 Bedrooms
5 Baths
14 Guests
288.47 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $132/Night
7 Nights - US $926
Cabin
- Chamberlain
- ·
- Kimball
- 7.82 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $289/Night
7 Nights - US $2,021
House
- Chamberlain
- ·
- Oacoma
- 0.08 mi to center
5 Bedrooms
3 Baths
10 Guests
2120.49 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Internet
US $480/Night
7 Nights - US $3,360
House
- South Dakota
- ·
- Chamberlain
- 4.25 mi to center
9.8Exceptional
(51 Reviews)
4 Bedrooms
1 Bath
10 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $367/Night
7 Nights - US $2,571
Cabin
- South Dakota
- ·
- Charles Mix County
- 12.21 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
1 Bath
18 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $344/Night
7 Nights - US $2,405
House
- Chamberlain
- ·
- Platte
- 19.10 mi to center
9.6Exceptional
(35 Reviews)
3 Bedrooms
2 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $344/Night
7 Nights - US $2,405
Other
- South Dakota
- ·
- Chamberlain
- 4.02 mi to center
9.6Exceptional
(4 Reviews)
6 Bedrooms
2 Baths
20 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $476/Night
7 Nights - US $3,330
House
10.0Exceptional
(15 Reviews)
4 Bedrooms
3 Baths
10 Guests
4300 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $459/Night
7 Nights - US $3,210
Wheelchair Accessible Holiday Homes in Winner
Over 11+ Wheelchair Accessible Holiday Homes in or Near Winner
Hotel
- Chamberlain
- ·
- Platte
- 7.72 mi to center
9.0Exceptional
(29 Reviews)
2 Baths
301.39 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Parking
US $104/Night
7 Nights - US $728
Hotel
8.6Fabulous
(476 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $127/Night
7 Nights - US $889
Hotel
8.2Excellent
(126 Reviews)
1 Bath
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $102/Night
7 Nights - US $714
Hotel
8.4Excellent
(647 Reviews)
1 Bath
- Hot Tub
- Spa
- Pool
- Breakfast
US $128/Night
7 Nights - US $893
Hotel
- Chamberlain
- ·
- Oacoma
- 0.83 mi to center
8.1Excellent
(264 Reviews)
11 Baths
573.42 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Spa
US $145/Night
7 Nights - US $1,017
Hotel
- South Dakota
- ·
- Chamberlain
- 1.44 mi to center
8.2Excellent
(1002 Reviews)
1 Bath
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $139/Night
7 Nights - US $974
Hotel
- South Dakota
- ·
- Chamberlain
- 0.99 mi to center
7.4Very Good
(531 Reviews)
7 Baths
269.1 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $94/Night
7 Nights - US $656
Hotel
7.1Very Good
(124 Reviews)
5 Baths
269.1 ft²
- Private Pool
- Hot Tub
- Pool
- Pet Friendly
US $141/Night
7 Nights - US $986
Hotel
- Chamberlain
- ·
- Kimball
- 1.51 mi to center
6.1Good
(172 Reviews)
3 Baths
150.69 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $52/Night
7 Nights - US $364
Winner Private Villas and Holiday Homes Under $200
Over 79+ Winner Private Villas and Holiday Homes Under $200
US $132/Night
7 Nights - US $925
New
Hotel
9.0Exceptional
(1 Review)
1 Bath
4305.56 ft²
- Pet Friendly
- Parking
- Air Conditioner
- Internet
US $106/Night
7 Nights - US $744
Hotel
9.4Exceptional
(1002 Reviews)
1 Bath
- Balcony/Terrace
- Breakfast
- Kitchen
- Parking
US $82/Night
7 Nights - US $573
US $132/Night
7 Nights - US $925
Hotel
- South Dakota
- ·
- Chamberlain
- 2.77 mi to center
8.4Excellent
(230 Reviews)
14 Baths
267.56 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $155/Night
7 Nights - US $1,085
US $130/Night
7 Nights - US $910
US $130/Night
7 Nights - US $910
US $128/Night
7 Nights - US $895
US $128/Night
7 Nights - US $895
Instantly Bookable Holiday Homes in Winner
Over 60+ Instantly Bookable Holiday Homes in or Near Winner
US $245/Night
7 Nights - US $1,716
US $245/Night
7 Nights - US $1,716
US $123/Night
7 Nights - US $858
US $123/Night
7 Nights - US $858
US $121/Night
7 Nights - US $850
US $121/Night
7 Nights - US $850
US $112/Night
7 Nights - US $783
US $109/Night
7 Nights - US $761
House
- South Dakota
- ·
- Chamberlain
- 0.07 mi to center
9.8Exceptional
(56 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $283/Night
7 Nights - US $1,978
Book a Last Minute Place to Stay in Winner
About Casai's Private Villas and Holiday Rentals in Winner
Discover more than 183 vacation rentals available in Winner. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Winner.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Winner, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Winner. On average, places to stay near Winner offer 423.27 ft², with nightly prices averaging US $220.
With Casai, finding and comparing holiday rentals in Winner is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Winner
| Type | Count |
|---|---|
| Vacation Homes | 61 |
| Holiday Apartments | 4 |
| Cottages | 1 |
Use these Quick Filters to Find a Holiday Rental in Winner
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Winner.
Weather in Winner, SD
View the weather forecast for Winner before booking your Winner Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Winner, SD
Casai offers a large selection of top attractions around Winner . Research things to do on your vacation before you visit Winner.
Other Places to Stay in Winner, SD
Frequently Asked Questions About Winner?
What are the top holiday rentals in Winner?
With numerous options available in Winner, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Winner:
- The Cats Meow- A little bit of country next to townn2 Dogs allowed with pet fee
- A Nebraska Sandhills get-a-way.
- Log Cabin located minutes from Missouri River, airport, I-90 and downtown.
- The Philing Station: Restored 1920's Gas Station. A retro vacation rental!
- Green Cedar Lodging - your play and stay destination.
- Store that boat inside! Blocks to boat ramps/Marina & Restaurant
- Missouri River Vacation Rentals at American Creek Campground, Chamberlain, SD
- Perfect lodging for fishermen, hunters and family gatherings! Sleeping for 12.
- Sportsman's cabin near the Missouri River
- The 69210 -A cozy getaway in small-town Nebraska.
How many holiday rentals have private pools in Winner?
Discover a selection of holiday rentals with private pools near Winner with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Winner are best for families?
If you're searching for a family-friendly holiday home in Winner, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Winner:
- 3 miles from Platte Creek boat dock & public hunting!
- Platte Vacation Rental ~ 3 Mi to Missouri River!
- American Inn
How many Casai.com holiday rentals are available in Winner?
As of 2026, Casai boasts over 183 properties listed in the Winner area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Winner.
People Also Ask
Finding the best prices in Winner
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