1. St. Barthelemy
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  3. Ski Chalets

Windward Ski Chalets

Villa
Map-icon
like-icon10.0
Exceptional
(36 Reviews)
4 Bedrooms 3 Baths 8 Guests 7000 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
R20,756/Night 7 Nights - R145,289
star-icons-4
Apartment
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like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 2 Baths 4 Guests 753.47 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
R10,970/Night 7 Nights - R76,791
Hotel
like-icon10.0
Exceptional
(87 Reviews)
1 Bath
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
R36,979/Night 7 Nights - R258,859
Villa
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like-icon10.0
Exceptional
(1 Review)
6 Bedrooms 6 Baths 12 Guests 2691 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R55,350/Night 7 Nights - R387,447
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Villa
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like-icon10.0
Exceptional
(1 Review)
8 Bedrooms 4 Baths 16 Guests 1937.51 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
R22,795/Night 7 Nights - R159,564
Villa
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like-icon10.0
Exceptional
(1 Review)
1 Bedroom 4 Baths 2 Guests 1615 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
R22,715/Night 7 Nights - R158,998
Villa
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like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 3 Baths 6 Guests 2152.78 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
R21,307/Night 7 Nights - R149,153
New
Villa
Map-icon
like-icon10.0
Exceptional
(1 Review)
3 Bedrooms 3 Baths 6 Guests 1000 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R20,287/Night 7 Nights - R142,007
Villa
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like-icon10.0
Exceptional
(1 Review)
4 Bedrooms 3 Baths 6 Guests 1722.23 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
R15,242/Night 7 Nights - R106,699
Villa
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like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 2 Baths 4 Guests 1615 ft²
  • Ocean View
    Ocean View
  • View
    View
More amenities
R16,643/Night 7 Nights - R116,496
star-icons-4
House
Map-icon
like-icon9.8
Exceptional
(12 Reviews)
4 Bedrooms 4 Baths 16 Guests 409.03 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
R12,973/Night 7 Nights - R90,807
Villa
Map-icon
like-icon9.8
Exceptional
(7 Reviews)
2 Bedrooms 2 Baths 4 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
R19,591/Night 7 Nights - R137,141

Why Choose Rent By Owner for your Windward Ski Chalets?

What makes our Ski Chalets special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Windward

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.

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

Quartier Lorient

Grand Cul-de-Sac

Barriere des Quatres Vents

Petit Cul-de-Sac

Morne de Depoudre

Grand Cul de Sac

Frequently Asked Questions About Windward Rental Ski Chalets

1. What are the top Ski Chalets in Windward?

There are a lot of options in Windward. If you plan on staying in the Windward 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:

2. How many Ski Chalets are available in Windward?

Currently, the total number of properties listed by RBO in 2026 is over 3554 in the Windward area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Windward. 

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Villa
like-icon9.7
Exceptional
(13 Reviews)
2 Bedrooms 1 Bath 4 Guests 75.35 ft²
  • Balcony/Terrace
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R14,527/Night 7 Nights - R101,688
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R148,744/Night 7 Nights - R1,041,206
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R148,744/Night 7 Nights - R1,041,206
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R135,359/Night 7 Nights - R947,505
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R135,359/Night 7 Nights - R947,505
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R134,040/Night 7 Nights - R938,274