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A lush green mountain with a white picket fence and buildings with red roofs.

Search Guest Houses in Windward Side from CA $221

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    Check prices for these dates, December 14–15, 2026

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    Our top choices for Windward Side guest houses

    1. Quill Gardens Boutique Hotel

    A pathway lined with palm trees and tropical plants, leading to a building with a blue facade.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Learn more about Windward Side

    Colourful cottages with red roofs dot this charming village where hikers begin their ascent of Mount Scenery. Grab a meal at Scout's Place after exploring the Saba Conservation Foundation's trail network that winds through cloud forests.

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    A lush green mountain with a white picket fence and buildings with red roofs.