Highland Beach Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, 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

DoubleTree by Hilton Hotel Annapolis

4 out of 5
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

DoubleTree by Hilton Hotel Annapolis
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
9/10 Wonderful! (1,889 reviews)
Room was clean, well decorated

Reviewed on Jan 11, 2026

Historic Inns of Annapolis
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

4 out of 5
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

Annapolis Waterfront Hotel, Autograph Collection
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

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.