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Search Hotels Near Annapolis Sailing School, Annapolis

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    • Check prices for these dates

    Check prices for these dates, 13 – 14 December 2026

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    Our top choices for Annapolis Sailing School hotels

    1. 86 State Circle - Luxury Boutique Hotel

    A church with a spire, surrounded by trees and illuminated by warm lights.

    2. Graduate by Hilton Annapolis

    A spacious atrium with a high ceiling, skylights, and a patterned floor.

    3. Flag House Inn

    A dining room with a fireplace, wooden chairs, a chandelier, and framed artwork on the walls.

    4. Historic Inns of Annapolis

    A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

    5. Residence Inn By Marriott Annapolis

    A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

    6. The Westin Annapolis

    A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

    7. Fairfield Inn & Suites By Marriott Annapolis

    A modern living room with a fireplace, a sofa, and a coffee table.

    8. Annapolis Waterfront Hotel, Autograph Collection

    A balcony with a table set for two, overlooking a marina with boats.

    9. Hilton Garden Inn Annapolis Downtown

    A modern lounge area with a sofa, chairs, a coffee table, and a bookshelf.

    10. Laurel Grove Inn on the South

    Land view from property

    11. The Inn at Chesapeake Bay Beach Club

    A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

    12. Microtel Inn & Suites by Wyndham Gambrills/Odenton

    A multi-story Microtel by Wyndham hotel with a parking lot and a landscaped area in front.

    13. Kent Island Resort

    A large, two-story barn-style building with a covered front porch and a garage.

    14. Country Inn & Suites by Radisson, Annapolis, MD

    A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

    15. TownePlace Suites by Marriott Annapolis

    A modern hotel room with a sofa set, armchairs, a coffee table, and a TV mounted on the wall.

    16. SpringHill Suites by Marriott Annapolis

    A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

    17. DoubleTree by Hilton Hotel Annapolis

    A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

    18. Crowne Plaza Annapolis by IHG

    A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

    19. Sonesta ES Suites Annapolis

    A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

    20. Candlewood Suites Annapolis by IHG

    A modern living room with a large window, a dining area, and a kitchen in the background.

    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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    Compare popular hotels close to Annapolis Sailing School

    PropertyProperty classGuest ratingBreakfast includedPoolSpaPet-friendlyWiFi included
    A church with a spire, surrounded by trees and illuminated by warm lights.
    86 State Circle - Luxury Boutique Hotel    		9.8Exceptional12 reviewsView
    A spacious atrium with a high ceiling, skylights, and a patterned floor.
    Graduate by Hilton Annapolis    		9.2Wonderful1,014 reviewsView
    A dining room with a fireplace, wooden chairs, a chandelier, and framed artwork on the walls.
    Flag House Inn    		9.2Wonderful101 reviewsView
    A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.
    Historic Inns of Annapolis    		9.0Wonderful2,066 reviewsView
    A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.
    Residence Inn By Marriott Annapolis    		9.0Wonderful95 reviewsView

    Other attractions near Annapolis Sailing School

    A marina with boats docked, wooden pilings, and a clear sky.

    Photo by Michael Lore

    Susan Campbell Park

    Susan Campbell Park is just one of the places to see in Annapolis, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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    A waterfront cityscape with a prominent clock tower, a marina with boats, and a mix of historic and modern buildings.

    Ego Alley

    Explore the waterfront in Annapolis with a trip to Ego Alley. While you're here, you can savour the top-notch restaurants.

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    A coastal town with a marina, houses, and a bridge in the distance.

    Spa Creek

    Commune with nature and explore the great outdoors at Spa Creek during your travels in Annapolis.

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    Annapolis Landing Marina

    Explore the waterfront in Annapolis with a trip to Annapolis Landing Marina. Stroll along the riverfront or experience the area's live music.

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    Annapolis Maritime Museum

    Rating: 9.0/10 (27 reviews)

    You can study the exhibits at Annapolis Maritime Museum, a museum with a storied past, during your travels to Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.

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    Sparrows Beach

    Why not spend a lazy afternoon at Sparrows Beach during your trip to Annapolis? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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    Annapolis Harbor

    Explore the waterfront in Annapolis with a trip to Annapolis Harbor.

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    Carrs Beach

    Why not spend a lazy afternoon at Carrs Beach during your trip to Annapolis? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

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    Top Annapolis Sailing School Hotel Reviews

    Graduate by Hilton Annapolis

    A spacious atrium with a high ceiling, skylights, and a patterned floor.

    Laurel Grove Inn on the South

    Land view from property

    Historic Inns of Annapolis

    A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

    The Inn at Chesapeake Bay Beach Club

    A large, multi-story building with a prominent red cylindrical tower, a covered patio area, and a well-maintained garden.

    Residence Inn By Marriott Annapolis

    A modern living room with a fireplace, a sofa, a coffee table, and a TV mounted on the wall.

    Country Inn & Suites by Radisson, Annapolis, MD

    A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

    SpringHill Suites by Marriott Annapolis

    A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

    DoubleTree by Hilton Hotel Annapolis

    A spacious lobby with a high ceiling, a central seating area with sofas and tables, and large windows with curtains.

    Frequently Asked Questions

    What's the area like around Annapolis Sailing School?

    Annapolis Sailing School is located in an area of Annapolis known for its interesting historical sites. If you're looking for a convenient place to stay, take a look at the 88 hotels and other accommodation options you'll find within a mile.

    What's the best place to stay near Annapolis Sailing School?

    Annapolis Waterfront Hotel, Autograph Collection is one of the top choices for your stay based on our traveller data, and this hotel offers a restaurant and a 24-hour fitness centre. It's located just a short 0.8 mi (1.4 km) from Annapolis Sailing School. Other good choices within 5 miles include Historic Inns of Annapolis and Graduate by Hilton Annapolis.

    How many hotels will I be able to find near Annapolis Sailing School?

    Expedia has 88 hotels and other accommodation options within a mile from Annapolis Sailing School.

    If I need to cancel the hotel reservation for my stay near Annapolis Sailing School, will I receive a refund?

    Yes, you'll find most hotel bookings are fully refundable as long as you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, you may still be able to cancel and get a refund within a 24-hour period of your booking. Add your dates and click on "Search", then you can filter by "fully refundable" to review the best options available near Annapolis Sailing School.

    What can I see and do near Annapolis Sailing School?

    Study the collections at Annapolis Maritime Museum, Hammond-Harwood House or London Town. Explore landmarks like William Paca House, 97, 99 and 101 East Street and Kunta Kinte Plaque & Alex Haley Memorial. You can enjoy live performances at The Colonial Players and Ballet Theater of Maryland.