Windward Ski Chalets
Cottage
10.0(101 Reviews)
1 Bedroom
1 Bath
2 Guests
Private Pool
Pool
Ocean View
Balcony/Terrace
US $386/Night
7 Nights - US $2,700
Apartment
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
Oceanfront- Pool
- Ocean View
- Balcony/Terrace
US $679/Night
7 Nights - US $4,750
US $2,287/Night
7 Nights - US $16,012
Villa
10.0(55 Reviews)
2 Bedrooms
2 Baths
4 Guests
1399 ft²
- Private Pool
- Pool
- Balcony/Terrace
Kitchen
US $605/Night
7 Nights - US $4,234
Villa
10.0(1 Review)
8 Bedrooms
4 Baths
16 Guests
1937.51 ft²
- Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
US $1,410/Night
7 Nights - US $9,870
Villa
10.0(36 Reviews)
4 Bedrooms
3 Baths
8 Guests
7000 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,284/Night
7 Nights - US $8,987
Villa
10.0(1 Review)
3 Bedrooms
3 Baths
6 Guests
2152.78 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,318/Night
7 Nights - US $9,226
Villa
10.0(28 Reviews)
2 Bedrooms
2 Baths
4 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
Pet Friendly
US $811/Night
7 Nights - US $5,674
Villa
10.0(1 Review)
4 Bedrooms
3 Baths
6 Guests
1722.23 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $943/Night
7 Nights - US $6,600
Villa
10.0(26 Reviews)
4 Bedrooms
4 Baths
9 Guests
3000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $1,982/Night
7 Nights - US $13,872
Villa
10.0(25 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,448/Night
7 Nights - US $24,136
Why Choose Rent By Owner for your Windward 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
How to Book Your Windward 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
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
Quartier Lorient
Morne Criquet
Pointe Milou
Grand Cul-de-Sac
Anse de Toiny
Barriere des Quatres Vents
Petit Cul-de-Sac
Gouverneur
Camaruche
Morne de Depoudre
Grand Cul de Sac
Windward Ski Chalets Frequently Asked Questions
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:
- Villa La Magnifica | Ocean View - Located in Beautiful Deve with Private Pool
- Boutique villa in les Hauts de Saint Jean with stunning Eden Rock view
- Villa Endeavour So private, breathtaking ocean views, direct from owner !
- Villa Yvantino beachfront (2 bedroom)
- Villa Caco (3 bedrooms)
- Villa Angelique - Luxury 4 Bedroom Villa with Private Pool - St Barts
- Villa La Vue
- Villa La Magnifica | Ocean View - Located in Magnificent Deve with Private Pool
- NEW, INTIMATE BUNGALOW WITH POOL
- Appartement St Jean, Saint-barthélemy
2. How many Ski Chalets are available in Windward?
Currently, the total number of properties listed by RBO in 2026 is over 3555 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.
More Rentals You May Like Near Windward
Villa
9.7(13 Reviews)
2 Bedrooms
1 Bath
4 Guests
75.35 ft²
- Balcony/Terrace
View
Parking
Air Conditioner
US $899/Night
7 Nights - US $6,290
Apartment
10.0(25 Reviews)
1 Bedroom
1 Bath
2 Guests
807 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $230/Night
7 Nights - US $1,609
Villa
10.0(21 Reviews)
3 Bedrooms
3 Baths
6 Guests
1507 ft²
- Private Pool
- Hot Tub
- Pool
- Balcony/Terrace
US $1,048/Night
7 Nights - US $7,334
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
3229 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,448/Night
7 Nights - US $24,136
Villa
10.0(16 Reviews)
7 Bedrooms
7 Baths
14 Guests
2153 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,448/Night
7 Nights - US $24,136
House
10.0(15 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $248/Night
7 Nights - US $1,736
Villa
10.0(13 Reviews)
2 Bedrooms
2 Baths
6 Guests
20451 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $932/Night
7 Nights - US $6,521
Villa
10.0(12 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,389/Night
7 Nights - US $23,723
Villa
10.0(12 Reviews)
4 Bedrooms
3 Baths
8 Guests
2150 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,415/Night
7 Nights - US $9,908
Villa
10.0(10 Reviews)
5 Bedrooms
4 Baths
8 Guests
3767 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,165/Night
7 Nights - US $8,156
Villa
10.0(10 Reviews)
3 Bedrooms
3 Baths
6 Guests
1712 ft²
- Private Pool
- Hot Tub
- Pool
- Ocean View
US $934/Night
7 Nights - US $6,539
Villa
10.0(10 Reviews)
2 Bedrooms
3 Baths
4 Guests
2153 ft²
- Pool
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $859/Night
7 Nights - US $6,013
