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

Search Historic Hotels in Windward Side

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    Check prices for these dates, 13 – 14 December 2026

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    Recommended hotels in Windward Side

    1. Saba Arawak Hotel

    A rectangular swimming pool with a white tiled deck, surrounded by white railings and lounge chairs.

    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 pool with lounge chairs and a stone patio, surrounded by lush greenery and overlooking a hilly 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 beach with palm trees, a stone wall, and a building in the background.

    6. Talk of the Town Inn & Suites

    A cozy room with a high ceiling, large windows, a sofa, two wicker chairs, and a wooden table.

    7. Quill Gardens Boutique Hotel

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

    8. Palm Spring Inn

    A paved pathway flanked by palm trees and buildings with a clear sky above.

    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 courtyard with a central paved area, surrounded by a white building with multiple floors and balconies.

    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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    Top Windward Side Hotel Reviews

    Saba Arawak Hotel

    A rectangular swimming pool with a white tiled deck, surrounded by white railings and lounge chairs.

    The Old Gin House

    A beach with palm trees, a stone wall, and a building in the background.

    Talk of the Town Inn & Suites

    A cozy room with a high ceiling, large windows, a sofa, two wicker chairs, and a wooden table.

    Frequently Asked Questions

    What should a history enthusiast expect from a trip to Windward Side?

    You'll probably want to seek out the historically relevant sites during your trip to Windward Side. Also explore all there is to see and do including the seaside and mountain views.

    How many historically relevant hotels will I find in Windward Side?

    Windward Side is home to 12 hotels and other lodging options bookable on Expedia though you won't find many designated historic hotels.

    What are the must-see historical sites and other places to visit in Windward Side?

    Windward Side is notable for landmarks like Dutch Museum of Saba. Cultural venues include Harry L Johnson Museum and Saba Heritage Center. A couple of additional sights to add to your itinerary are Mt Scenery and Jo Bean Glass Art Studio.

    What is a historic hotel like in Windward Side?

    A guest who chooses a historic hotel has an opportunity to stay in a place that's been officially recognised with a historic designation. Historic hotels throughout the world come in all forms like castles, stately homes, palaces or even pubs, lodges, old police stations or skyscrapers — any place of special interest. These types of hotels in Windward Side typically retain original characteristics like traditional architecture and period features in guestrooms or communal spaces.

    What is the difference between a historic hotel and a heritage hotel?

    They are quite similar. "Historic hotel" is a term often used in the US, while "heritage hotel" is often used in Asia and Europe. Historic hotels tend to place more significance on the physical building and architecture. Heritage hotels draw their meaning mainly from the cultural value and how it inspired the surrounding community.

    Do historic hotels in Windward Side have modern facilities?

    Yes. Every effort is made to preserve treasured traditions and historic facades, while interiors have safety features and modern conveniences. Guests should expect the popular amenities from a contemporary hotel such as WiFi, heating and air conditioning, and updated bathroom facilities. In Windward Side, booking a historic hotel doesn't mean you will stay in a place that's uncomfortable for guests or simply rundown.