Windward Side Ski Chalets
Villa
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
Private Pool
Oceanfront
Pool
Ocean View
R12,660/Night
7 Nights - R88,616
Apartment
9.4(14 Reviews)
1 Bedroom
1 Bath
2 Guests
753.47 ft²
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
R4,187/Night
7 Nights - R29,314
Resort
9.8(7 Reviews)
1 Bath
- Balcony/Terrace
Kitchen
Air Conditioner
Child Friendly
R5,467/Night
7 Nights - R38,274
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
Internet
R5,569/Night
7 Nights - R38,981
Resort
9.3(76 Reviews)
7 Baths
19 Guests
612 ft²
- Oceanfront
Spa
Fireplace/Heating- Pool
R5,576/Night
7 Nights - R39,030
House
10.0(2 Reviews)
3 Bedrooms
2 Baths
7 Guests
1400 ft²
- Ocean View
- Balcony/Terrace
View- Kitchen
R2,178/Night
7 Nights - R15,257
House
9.0(8 Reviews)
3 Bedrooms
3 Baths
3 Guests
753.47 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R4,110/Night
7 Nights - R28,771
Apartment
7.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
Parking- Air Conditioner
R3,097/Night
7 Nights - R21,685
Apartment
8.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
R1,332/Night
7 Nights - R9,322
New
House
3 Bedrooms
3 Baths
8 Guests
Pet Friendly- Air Conditioner
- Internet
- Child Friendly
R6,224/Night
7 Nights - R43,568
Apartment
7.8(12 Reviews)
2 Bedrooms
2 Baths
6 Guests
656.6 ft²
- Balcony/Terrace
- View
Breakfast- Pet Friendly
R2,183/Night
7 Nights - R15,273
Apartment
2 Bedrooms
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
R3,847/Night
7 Nights - R26,930
Why Choose Rent By Owner for your Windward Side Ski Chalets?
What makes our Ski Chalets special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Windward Side
How to Book Your Windward Side Ski Chalets
What's our booking process?
Our platform allows you to browse a curated selection of ski chalets. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Windward Side
Common Ski Chalets Amenities
What amenities can you expect?
Our Ski Chalets are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Windward Side
Harry L Johnson Museum
Jo Bean Glass Art Studio
Dutch Museum of Saba
Mt Scenery
Frequently Asked Questions About Windward Side Rental Ski Chalets
1. What are the top Ski Chalets in Windward Side?
There are a lot of options in Windward Side. If you plan on staying in the Windward Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Ski Chalets in Windward Side:
2. How many Ski Chalets are available in Windward Side?
Currently, the total number of properties listed by RBO in 2026 is over 59 in the Windward Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Windward Side.
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House
7.6(59 Reviews)
7 Bedrooms
7 Baths
15 Guests
350.6 ft²
- Balcony/Terrace
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- Breakfast
- Parking
R2,499/Night
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Apartment
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1 Bath
6 Guests
- Air Conditioner
- Internet
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Villa
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3 Bedrooms
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- Private Pool
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Villa
5.0(2 Reviews)
2 Bedrooms
3 Baths
4 Guests
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House
5.0(2 Reviews)
2 Bedrooms
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4 Guests
1000 ft²
- Private Pool
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R4,061/Night
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Cottage
5.0(2 Reviews)
2 Bedrooms
2 Baths
6 Guests
938 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
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R3,107/Night
7 Nights - R21,751
Villa
5.0(1 Review)
3 Bedrooms
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6 Guests
- Pet Friendly
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R7,286/Night
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Villa
4.9(59 Reviews)
3 Bedrooms
3 Baths
4 Guests
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- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
R6,593/Night
7 Nights - R46,149
Villa
4.9(9 Reviews)
5 Bedrooms
5 Baths
12 Guests
2900 ft²
- Private Pool
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R6,247/Night
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