Highland Beach Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Find the Best Highland Beach Vacation Packages
Highland Beach Hotel Deals
Historic Inns of Annapolis
58 State Circle Annapolis MD
8.8/10 Excellent! (1,910 reviews)
Excellent hotel Really nice staff Love the valet guys
Reviewed on Nov 30, 2025
Graduate by Hilton Annapolis
126 West St Annapolis MD
The price is ₩180,806 per night from Dec 21 to Dec 22
₩180,806
₩206,118 total
Dec 21 - Dec 22
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
Clean rooms, comfortable beds, friendly staff.
Reviewed on Nov 28, 2025
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ₩83,362 per night from Dec 21 to Dec 22
₩83,362
₩95,033 total
Dec 21 - Dec 22
includes taxes & fees
8.6/10 Excellent! (1,027 reviews)
Clean, friendly staff. Restaurant/ bar food was excellent and staff in the restaurant/ bar were fun and accommodating!
Reviewed on Nov 26, 2025
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
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.
Chesapeake Bay Bridge
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
