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
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ₩109,699 per night from Feb 8 to Feb 9
₩109,699
₩125,057 total
Feb 8 - Feb 9
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
Clean and we moved to a quiet room as well
Reviewed on Jan 8, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,889 reviews)
Room was clean, well decorated
Reviewed on Jan 11, 2026
Annapolis Waterfront Hotel, Autograph Collection
80 Compromise St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ₩272,773 per night from Jan 25 to Jan 26
₩272,773
₩310,961 total
Jan 25 - Jan 26
includes taxes & fees
8.8/10 Excellent! (897 reviews)
Very welcoming and room very clean.
Reviewed on Jan 4, 2026
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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
