Highland Beach Vacations

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Find the Best Highland Beach Vacation Packages

Highland Beach Hotel Deals

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩141,089 per night from Sep 7 to Sep 8
₩141,089
₩208,186 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (1,745 reviews)
"Perfect location and beautiful, old building. Love the history of the building!"

Reviewed on Aug 26, 2025

Historic Inns of Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is ₩140,029 per night from Sep 7 to Sep 8
₩140,029
₩159,632 total
Sep 7 - Sep 8
includes taxes & fees
Country Inn & Suites by Radisson, Annapolis, MD
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is ₩248,605 per night from Sep 21 to Sep 22
₩248,605
₩283,410 total
Sep 21 - Sep 22
includes taxes & fees
Graduate by Hilton Annapolis
See all 1,227 properties in Highland Beach
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.

Discover the most popular places to visit in Highland Beach

U.S. Naval Academy which includes military items, interior views and heritage architecture

U.S. Naval Academy

See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.

U.S. Naval Academy
Chesapeake Bay Bridge

Chesapeake Bay Bridge

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Chesapeake Bay Bridge
Maryland Quiet Waters Park which includes a garden

Maryland Quiet Waters Park

Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.

Maryland Quiet Waters Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.