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

Search Windward Side Cottage Rentals from CA $139

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    Check prices for these dates, December 13–14, 2026

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    Recommended hotels in Windward Side

    1. Saba Arawak Hotel

    A hotel with a balcony, a view of a hill, and a clear sky.

    2. Scenery Hotel Saba

    A pool area with lounge chairs, a pergola, and a view of a mountain.

    3. Home a way from home in the Unspoiled queen of the Caribbean.

    A covered outdoor seating area with blue chairs and a pool, overlooking a mountainous landscape.

    4. Cattleya Flor Hotel

    A hotel room with a bed, a chair, a table with a vase of flowers, and a mirror on the wall.

    5. The Old Gin House

    A two-story building with a balcony, surrounded by lush tropical plants and a sign for 'The Old Sun House Restaurant Bar'.

    6. Talk of the Town Inn & Suites

    A bedroom with a large bed, a window with a view, a painting on the wall, and a wooden door.

    7. Quill Gardens Boutique Hotel

    A swimming pool with clear blue water, surrounded by a wooden deck and blue railings.

    8. Palm Spring Inn

    A corridor with a door, a chair, and a railing with plants.

    9. Spacious 2-bedroom apartment in Sint Eustatius with beautiful sunset views

    An outdoor patio with a table and chairs, a wicker sofa, and a view of the ocean.

    10. Charming 1-bedroom apartment with AC, WiFi in amazing Oranjestad

    A residential area with a paved courtyard, a white building with a balcony, and surrounding greenery.

    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.

    See all hotels in Windward Side

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

    Top reviews in Windward Side

    Saba Arawak Hotel

    A hotel with a balcony, a view of a hill, and a clear sky.

    Quill Gardens Boutique Hotel

    A swimming pool with clear blue water, surrounded by a wooden deck and blue railings.

    The Old Gin House

    A two-story building with a balcony, surrounded by lush tropical plants and a sign for 'The Old Sun House Restaurant Bar'.