- Air Conditioner
- Pool
- TV
Cottages in Windward Side
Stay in a Cottages in Windward Side – Plan Your Next Vacation to Windward Side Today!
Guests
Find the Best Cottages for Your Windward Side Trip
Smartours makes it easy to discover stays that match your style, budget, and location.
Why Book Your Trip to Windward Side with Smartours?
Here’s why smart travelers plan travel with Smartours
Smarter Stays
Cottages selected for comfort, location and value – giving you the ideal base for your adventures.
Smarter Itineraries
AI-powered trip plans that bundle accommodations, transport, and activities into flexible packages you can tailor to your style and budget.
Smarter Exploration
Self-guided itineraries filled with local insights, hidden gems, and authentic experiences beyond the typical tourist trail.
How to Book Your Stay in Windward Side?
What’s the Smartours booking process?
Our platform connects you to a curated selection of Cottages in Windward Side. Once you’ve found your ideal property, you’ll be redirected to our trusted booking partner to complete your reservation securely and with confidence.
Booking Steps
Search Stays
Use Smartours filters to find accommodations that match your style, location preferences, and budget.
View Details
Click on a listing to see photos, amenities, reviews, and pricing.
Book Securely
Follow the link to finalize your reservation directly with our verified booking partner.
Common Trip Amenities in Windward Side?
What amenities can you expect on your Smartours trip?
Our handpicked Cottages in Windward Side are chosen for comfort, convenience, and style — often with thoughtful extras to make your trip even more memorable. Here’s what you might look forward to
Indoor Features
- Fully equipped kitchens or kitchenettes
- Comfortable living areas with smart TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-room coffee and tea facilities
- Premium bedding for restful nights
- Modern bathrooms with walk-in showers or soaking tubs
Outdoor Amenities
- Balconies, terraces, or rooftop lounges with scenic views
- Swimming pools, either private or shared
- Outdoor dining spaces with BBQ or grill access
- Gardens or courtyards for relaxing downtime
- On-site parking or easy transport access
- Proximity to key attractions, markets, or nature trails
Seasonal Weather in Windward Side
What’s the weather like in Windward Side throughout the year?
Windward Side’s climate varies by region, but most areas enjoy mild to warm weather year-round. Coastal cities benefit from ocean breezes, while inland areas and the desert see greater temperature swings between day and night.
Frequently Asked Questions
What are the top rated Cottage Rentals 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 Cottage Rentals in Windward Side:
- Saba Arawak Hotel
- Scenery Hotel Saba
- Haiku House, an amazing wooden villa situated in a tropical forest
- Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
- Beautiful Traditional Saba Cottage With all the Modern Amenities
- El Momo Cottages
- Saba Arawak Hotel
- Queen’s hotel, bar & kitchen
- Caribbean Elegance & Comfort
- Home a way from home in the Unspoiled queen of the Caribbean.
How much does it cost to rent a cottage in Windward Side?
The average cost for a cottage rental in Windward Side is $206 per night. Smartours has a wide list of great cottages near Windward Side that would suit your needs. There are single and multiple rooms for solo trips or family vacations.
Are there any cottages in Windward Side that allow pets?
Yes, here are the top cottage rentals in Windward Side that allow you to bring your pet:
- Compass Cottage: Breathtaking Views on Saba, the Caribbean’s “Unspoiled Queen”
- El Momo Cottages
- Historic Saban cottage in Windwardside, all amenities only a 2 minute walk away!
- Beautiful Gingerbread Cottage - Spectacular View & Pool
- Spyglass is a Private Villa With 360 View Near Windwardside.
- Saba Arawak Hotel
- El Momo Cottages
- Modern Luxury Private Villa w Pool and Ocean Views. Walk to Beach. Sleeps 6.
See all pet-friendly vacation rentals in Windward Side on Smartours
Do you have any rental cottages in Windward Side that are suitable for families?
Most of our listed cottages are suitable for families. Check out the complete list of cottages in Windward Side to find one that works for you.
Are there quality cottages in Windward Side that have indoor swimming pools?
As of 2026, the data from Smartours shows that there are Over 6 private swimming pools or cottages with indoor pools in the Windward Side area along with other great amenities.




