Windward Islands Ski Chalets

10.0
Exceptional
(7 Reviews)
377 ft² 2 Guests 1 Bedroom 2 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
US $108/Night For 7 Nights US $758
9.9
Exceptional
(16 Reviews)
660.19 ft² 16 Guests 4 Bedrooms 3 Bathrooms
Free Cancellation Ski Chalet
  • Balcony/Terrace
  • View
  • Parking
US $132/Night For 7 Nights US $923
10.0
Exceptional
(5 Reviews)
377 ft² 2 Guests 1 Bedroom 2 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
US $108/Night For 7 Nights US $758
9.7
Exceptional
(6 Reviews)
215.28 ft² 2 Guests 1 Bedroom 1 Bathroom
Free Cancellation Ski Chalet
  • Balcony/Terrace
  • View
  • Parking
US $100/Night For 7 Nights US $700
10.0
Exceptional
(3 Reviews)
323 ft² 3 Guests 1 Bedroom 1 Bathroom
Family Friendly Ski Chalet
  • Pool
  • Balcony/Terrace
  • Kitchen
US $167/Night For 7 Nights US $1,167
9.7
Exceptional
(3 Reviews)
904.17 ft² 4 Guests 2 Bedrooms 1 Bathroom
Free Cancellation Ski Chalet
  • Private Beach
  • Oceanfront
  • Ocean View
US $158/Night For 7 Nights US $1,107
10.0
Exceptional
(2 Reviews)
1346 ft² 8 Guests 2 Bedrooms 2 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
US $353/Night For 7 Nights US $2,468
9.5
Exceptional
(139 Reviews)
457.47 ft² 7 Guests 3 Bedrooms 3 Bathrooms
Ocean View Ski Chalet
  • Oceanfront
  • Pool
  • Ocean View
US $113/Night For 7 Nights US $791
10.0
Exceptional
(2 Reviews)
861 ft² 10 Guests 1 Bedroom 1 Bathroom
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Pet Friendly
  • Kitchen
US $335/Night For 7 Nights US $2,343
9.5
Exceptional
(41 Reviews)
753.47 ft² 3 Guests 1 Bedroom 1 Bathroom
Free Cancellation Ski Chalet
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
US $132/Night For 7 Nights US $923
10.0
Exceptional
(2 Reviews)
430 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View Ski Chalet
  • Private Pool
  • Oceanfront
  • Pool
US $185/Night For 7 Nights US $1,293
9.5
Exceptional
(13 Reviews)
376.74 ft² 3 Guests 1 Bedroom 1 Bathroom
Free Cancellation Ski Chalet
  • Balcony/Terrace
  • View
  • Parking
US $105/Night For 7 Nights US $734

Why Choose Rent By Owner for your Windward Islands 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 Islands

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

Windward Islands Ski Chalets Frequently Asked Questions

1. What are the top Ski Chalets in Windward Islands?

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

2. How many Ski Chalets are available in Windward Islands?

Currently, the total number of properties listed by RBO in 2026 is over 71 in the Windward Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Ski Chalets in Windward Islands. 

More Rentals You May Like Near Windward Islands

10.0
Exceptional
(2 Reviews)
538 ft² 4 Guests 1 Bedroom 2 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
US $118/Night For 7 Nights US $825
10.0
Exceptional
(2 Reviews)
753 ft² 4 Guests 1 Bedroom 1 Bathroom
Family Friendly Ski Chalet
  • Pool
  • Balcony/Terrace
  • Kitchen
US $117/Night For 7 Nights US $820
10.0
Exceptional
(1 Review)
861 ft² 8 Guests 3 Bedrooms 2 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
US $260/Night For 7 Nights US $1,823
10.0
Exceptional
(1 Review)
969 ft² 5 Guests 2 Bedrooms 1 Bathroom
Ocean View Ski Chalet
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
US $178/Night For 7 Nights US $1,246
10.0
Exceptional
(1 Review)
646 ft² 4 Guests 1 Bedroom 2 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
US $172/Night For 7 Nights US $1,201
10.0
Exceptional
(1 Review)
807 ft² 6 Guests 2 Bedrooms 1 Bathroom
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Internet
US $160/Night For 7 Nights US $1,119
9.6
Exceptional
(23 Reviews)
2 Guests 1 Bedroom 1 Bathroom
Ocean View Ski Chalet
  • Pool
  • Ocean View
  • Balcony/Terrace
US $155/Night For 7 Nights US $1,087
9.0
Exceptional
(8 Reviews)
1076 ft² 9 Guests 4 Bedrooms 4 Bathrooms
Family Friendly Ski Chalet
  • Private Pool
  • Pool
  • Balcony/Terrace
US $301/Night For 7 Nights US $2,110
9.0
Exceptional
(2 Reviews)
646 ft² 4 Guests 1 Bedroom 2 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Internet
US $199/Night For 7 Nights US $1,390
9.0
Exceptional
(2 Reviews)
323 ft² 3 Guests 1 Bedroom 1 Bathroom
Family Friendly Ski Chalet
  • Pool
  • Balcony/Terrace
  • Kitchen
US $101/Night For 7 Nights US $707
8.8
Fabulous
(5 Reviews)
1722 ft² 16 Guests 5 Bedrooms 4 Bathrooms
Ocean View Ski Chalet
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
US $526/Night For 7 Nights US $3,679
8.6
Fabulous
(4 Reviews)
538 ft² 4 Guests 1 Bedroom 2 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
US $120/Night For 7 Nights US $837