Hotels in Highland Beach, Annapolis

  • Overview

    Highland Beach is a charming town located in Maryland, United States of America. Situated along the Chesapeake Bay, it offers picturesque views and a serene coastal atmosphere. The area is known for its beautiful sandy beaches, peaceful waterfront parks, and scenic walking trails. Highland Beach is also rich in history, as it was established in 1893 as a vacation retreat for African American families, and has since become a symbol of African American heritage and pride. The town features a mix of historic cottages and modern waterfront homes, creating a unique and charming setting for visitors to enjoy.

  • When to visit

    The best time to visit Highland Beach is during the summer months, from June to August, when the weather is warm and ideal for enjoying the beach and outdoor activities. The town comes alive during this time with various events and festivals celebrating its history and culture. However, Highland Beach can be enjoyed year-round, as its scenic beauty and peaceful ambiance make for a delightful experience in any season.

  • Reasons to Visit

    Highland Beach is the perfect destination for those seeking relaxation and tranquility. Its pristine beaches provide opportunities for swimming, sunbathing, and picnicking, while the surrounding parks offer walking and biking trails for outdoor enthusiasts. The town's rich history and heritage make it a fascinating place to visit, offering insight into the African American experience and the development of coastal retreats. Whether you want to explore the town's cultural heritage, enjoy waterfront activities, or simply unwind in a peaceful seaside setting, Highland Beach has something to offer for everyone.

  • Nearby Attractions

  • Highland Beach Museum

    Discover the rich history and heritage of Highland Beach at the town's museum. It showcases artifacts, photographs, and exhibits that highlight the African American vacation retreat and its significance in coastal history.

  • Baywalk Park

    Baywalk Park is a waterfront park that offers stunning views of the Chesapeake Bay. It features walking paths, picnic areas, and benches where visitors can relax and enjoy the beautiful surroundings.

  • Highland Beach Heritage Trail

    Embark on a journey through Highland Beach's past by walking the Heritage Trail. This self-guided trail takes you through historic landmarks and provides insights into the town's founding, development, and cultural significance.

  • Highland Beach Clubhouse

    Visit the Highland Beach Clubhouse, a community gathering spot that hosts various events and activities throughout the year. It offers a glimpse into the town's vibrant social life and is a great place to meet locals and learn more about the area.

  • Hotels

  • 1313 West Luxury Boutique Hotel

    - Make yourself at home in one of the 7 guestrooms. Complimentary wireless internet access is available to keep you connected. Conveniences include a turndown service and blackout drapes/curtains, and h Next available price is on . 1313 West Luxury Boutique Hotel

  • 134 Prince - Luxury Boutique Hotel

    - Make yourself at home in one of the 5 guestrooms featuring free minibar items and Smart televisions. Your memory foam bed comes with down comforters and Frette Italian sheets. Complimentary wireless i Next available price is on . 134 Prince - Luxury Boutique Hotel

  • Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!

    - Boasting lake views, Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER! features accommodation with a garden and a patio, around 14 km from Annapolis Harbor. This beach Next available price is on . Annapolis Charm Waterfront Getaway Near USNA - FISH & CRAB from your PRIVATE PIER!

  • Annapolis Waterfront Hotel, Autograph Collection

    - Make yourself at home in one of the 149 guestrooms featuring refrigerators and flat-screen televisions. Your pillowtop bed comes with down comforters and premium bedding. Complimentary wireless intern Next available price is on . Annapolis Waterfront Hotel, Autograph Collection

  • Best Western Annapolis

    - Make yourself at home in one of the 98 air-conditioned rooms featuring refrigerators and microwaves. 43-inch LED televisions with satellite programming provide entertainment, while complimentary wirel Next available price is 209.61 on Sept. 19, 2025. Best Western Annapolis

  • COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

    - Set in Annapolis, 48 km from Carroll Park and 48 km from Sports Legends Museum at Camden Yards, COZY DOWNTOWN APARTMENT-Naval Academy Vicinity offers air conditioning. The property is around 48 km fro Next available price is on . COZY DOWNTOWN APARTMENT-Naval Academy Vicinity

  • Capital Hotel Annapolis

    - Boasting a bar, Capital Hotel Annapolis is situated in Annapolis in the Maryland region, 2.4 km from Annapolis Harbor and 47 km from Carroll Park. This 3-star hotel offers room service. Sports Legends Next available price is on . Capital Hotel Annapolis

  • Captain's Quarters - Eastport!

    - Featuring a spa bath, Captain's Quarters - Eastport! is located in Annapolis. This property offers access to a patio, free private parking and free WiFi. The property is non-smoking and is set 1.5 km Next available price is on . Captain's Quarters - Eastport!

  • Captain’s Retreat! Newly Renovated - Beach House!

    - Set in Annapolis in the Maryland region and Annapolis Harbor reachable within 8.4 km, Captain’s Retreat! Newly Renovated - Beach House! offers accommodation with free WiFi, a children's playground, a Next available price is on . Captain’s Retreat! Newly Renovated - Beach House!

  • Courtyard by Marriott Annapolis

    - Make yourself at home in one of the 149 individually decorated guestrooms. Rooms have private balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is Next available price is 276.21 on Sept. 19, 2025. Courtyard by Marriott Annapolis

  • Crowne Plaza Annapolis, an IHG Hotel

    - Make yourself at home in one of the 197 guestrooms featuring refrigerators and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available f Next available price is on . Crowne Plaza Annapolis, an IHG Hotel

  • DoubleTree by Hilton Hotel Annapolis

    - Make yourself at home in one of the 219 guestrooms featuring refrigerators and LCD televisions. Your pillowtop bed comes with premium bedding. Complimentary wired and wireless internet access keeps yo Next available price is on . DoubleTree by Hilton Hotel Annapolis

  • Fisher House - Downtown Annapolis!

    - Situated in Annapolis, 1.7 km from Annapolis Harbor and 48 km from Carroll Park, Fisher House - Downtown Annapolis! features air-conditioned accommodation with a patio and free WiFi. The property is s Next available price is on . Fisher House - Downtown Annapolis!

  • Flag House Inn

    - Make yourself at home in one of the 5 individually decorated guestrooms, featuring free minibar items and espresso makers. Your memory foam bed comes with Frette Italian sheets. 55-inch LED television Next available price is on . Flag House Inn

  • Graduate by Hilton Annapolis

    - Stay in one of 215 guestrooms featuring Smart televisions. Your pillowtop bed comes with Egyptian cotton sheets. Wired and wireless internet access is complimentary, and flat-screen televisions with s Next available price is 500.65 on Sept. 19, 2025. Graduate by Hilton Annapolis

  • Hampton Inn & Suites Annapolis

    - Make yourself at home in one of the 117 individually furnished guestrooms, featuring refrigerators and microwaves. Your pillowtop bed comes with premium bedding. Wired and wireless internet access is Next available price is on . Hampton Inn & Suites Annapolis

  • Hilton Garden Inn Annapolis

    - Make yourself at home in one of the 126 guestrooms featuring refrigerators and LCD televisions. Wired and wireless internet access is complimentary, while DVD players and premium TV channels are also Next available price is on . Hilton Garden Inn Annapolis

  • Hilton Garden Inn Annapolis Downtown

    - Make yourself at home in one of the 121 guestrooms featuring refrigerators and microwaves. Wired and wireless internet access is complimentary, and LED televisions with digital programming provide ent Next available price is on . Hilton Garden Inn Annapolis Downtown

  • Historic Inns of Annapolis

    - Stay in one of 124 guestrooms featuring flat-screen televisions. Your bed comes with down comforters and premium bedding. Complimentary wireless internet access keeps you connected, and digital progra Next available price is 255.55 on Sept. 19, 2025. Historic Inns of Annapolis

  • Holiday Inn Express & Suites Annapolis, an IHG Hotel

    - Make yourself at home in one of the 79 guestrooms featuring refrigerators and microwaves. LED televisions with cable programming provide entertainment, while complimentary wireless internet access kee Next available price is 271.44 on Sept. 19, 2025. Holiday Inn Express & Suites Annapolis, an IHG Hotel

  • Inn at Horn Point

    - Make yourself at home in one of the 3 individually decorated guestrooms. Your pillowtop bed comes with Egyptian cotton sheets. Complimentary wireless internet access is available to keep you connected Next available price is on . Inn at Horn Point

  • Inn on Main Annapolis

    - Set within 1.9 km of Annapolis Harbor and 48 km of Carroll Park, Inn on Main Annapolis provides rooms with air conditioning and a private bathroom in Annapolis. Housed in a building dating from 19th c Next available price is on . Inn on Main Annapolis

  • Searenity Stays

    - Set in Edgewater in the Maryland region and Triton Beach reachable within 700 metres, Searenity Stays offers accommodation with free WiFi, a children's playground, a private beach area and free privat Next available price is on . Searenity Stays

  • Spectacular Location Two Bedroom State Circle Apartment

    - Located in Annapolis, 2.4 km from Annapolis Harbor and 48 km from Carroll Park, Spectacular Location Two Bedroom State Circle Apartment offers a garden and air conditioning. The property has garden an Next available price is on . Spectacular Location Two Bedroom State Circle Apartment

  • SpringHill Suites by Marriott Annapolis

    - Make yourself at home in one of the 120 air-conditioned rooms featuring microwaves and Smart televisions. Your room comes with a pillowtop bed, and all rooms are furnished with queen sofa beds. Wired Next available price is 363.39 on Sept. 20, 2025. SpringHill Suites by Marriott Annapolis

  • The Compass Rose by Leavetown Vacations

    - Situated in Annapolis, 6.7 km from Annapolis Harbor and 46 km from Addison Road-Seat Pleasant, The Compass Rose by Leavetown Vacations offers a garden and air conditioning. This beachfront property of Next available price is on . The Compass Rose by Leavetown Vacations

  • The Westin Annapolis

    - Stay in one of 225 guestrooms featuring flat-screen televisions. Your pillowtop bed comes with premium bedding. Wireless internet access (surcharge) is available to keep you connected. Private bathroo Next available price is 189.05 on Sept. 21, 2025. The Westin Annapolis

  • Village Inn

    - Make yourself at home in one of the 60 air-conditioned rooms featuring refrigerators and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for Next available price is on . Village Inn

  • Waterfront Getaway, Dock Your Boat & Play!

    - Offering sea views, Waterfront Getaway, Dock Your Boat & Play! is an accommodation set in Edgewater, 22 km from Annapolis Harbor and 38 km from Addison Road-Seat Pleasant. This property offers access Next available price is on . Waterfront Getaway, Dock Your Boat & Play!
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29 hotels in Highland Beach