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
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ₩263,318 per night from May 3 to May 4
₩263,318
₩300,183 total
May 3 - May 4
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
Outstanding
Reviewed on Apr 11, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ₩222,108 per night from May 3 to May 4
₩222,108
₩303,145 total
May 3 - May 4
includes taxes & fees
9/10 Wonderful! (1,846 reviews)
I parked at the public garage close by and reasonably priced.
Reviewed on Apr 17, 2026
Hilton Garden Inn Annapolis Downtown
174 West Street Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ₩178,417 per night from May 4 to May 5
₩178,417
₩203,395 total
May 4 - May 5
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Everithing was so good , the room.so clean , the location was perfect
Reviewed on Apr 18, 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
4.5/5(450 reviews)
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
4/5(273 reviews)
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.
