Windward Side Ski Chalets
6 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
AU $1,090/Night
For 7 Nights AU $7,628
753.47 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Pool
- Ocean View
AU $360/Night
For 7 Nights AU $2,523
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Balcony/Terrace
- Kitchen
AU $156/Night
For 7 Nights AU $1,094
1400 ft²
7 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Ocean View
- Balcony/Terrace
- View
AU $188/Night
For 7 Nights AU $1,313
612 ft²
19 Guests
40 Bedrooms
7 Bathrooms
Free Cancellation
Resort
- Oceanfront
- Spa
- Fireplace/Heating
AU $480/Night
For 7 Nights AU $3,360
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Kitchen
- Parking
- Air Conditioner
AU $374/Night
For 7 Nights AU $2,617
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Balcony/Terrace
- Parking
- Air Conditioner
AU $115/Night
For 7 Nights AU $802
2 Bedrooms
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Parking
AU $294/Night
For 7 Nights AU $2,061
350.6 ft²
15 Guests
7 Bedrooms
7 Bathrooms
Group Friendly
House
- Balcony/Terrace
- View
- Breakfast
AU $209/Night
For 7 Nights AU $1,466
6 Guests
2 Bedrooms
1 Bathroom
Apartment
- Air Conditioner
- Internet
- Child Friendly
AU $282/Night
For 7 Nights AU $1,973
696.07 ft²
10 Guests
5 Bedrooms
3 Bathrooms
Free Cancellation
Apartment
- Balcony/Terrace
- View
- Breakfast
AU $188/Night
For 7 Nights AU $1,315
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Parking
AU $227/Night
For 7 Nights AU $1,589
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 56 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.
More Rentals You May Like Near Windward Side
376.74 ft²
4 Guests
8 Bedrooms
2 Bathrooms
Free Cancellation
Cabin
- Pool
- Balcony/Terrace
- View
AU $149/Night
For 7 Nights AU $1,040
1 Bedroom
1 Bathroom
Family Friendly
Apartment
- Balcony/Terrace
- Kitchen
- Parking
AU $227/Night
For 7 Nights AU $1,589
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Ocean View
- View
- Kitchen
AU $122/Night
For 7 Nights AU $853
6 Guests
3 Bedrooms
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
AU $1,431/Night
For 7 Nights AU $10,014
4 Guests
2 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
AU $606/Night
For 7 Nights AU $4,240
1000 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
AU $350/Night
For 7 Nights AU $2,447
938 ft²
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $267/Night
For 7 Nights AU $1,872
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Villa
- Pet Friendly
- Child Friendly
AU $627/Night
For 7 Nights AU $4,390
1500 ft²
4 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
Villa
- Balcony/Terrace
- Kitchen
- Air Conditioner
AU $568/Night
For 7 Nights AU $3,973
2900 ft²
12 Guests
5 Bedrooms
5 Bathrooms
Family Friendly
Villa
- Private Pool
- Pool
- Balcony/Terrace
AU $538/Night
For 7 Nights AU $3,764
900 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Cottage
- Private Pool
- Pool
- Balcony/Terrace
AU $297/Night
For 7 Nights AU $2,080
6 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Kitchen
AU $531/Night
For 7 Nights AU $3,715
