Highland Beach Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp173.195 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

Top hotels in Highland Beach

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 Rp1.261.399 per night from 4 Jan to 5 Jan
Rp1.261.399
Rp1.437.995 total
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
We stayed there for 7 days and loved it. The breakfast was so good (the bagel with bacon, cheddar cheese, and egg was delicious)! We loved the large TV in the room, the beds were very comfy, the room was spacious and we were so grateful that the staff wiped off the cars after it snowed. The fire ...

Reviewed on 18 Dec 2025

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
8.8/10 Excellent! (1,904 reviews)
Great customer service!

Reviewed on 21 Dec 2025

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is Rp1.779.422 per night from 25 Jan to 26 Jan
Rp1.779.422
Rp2.028.542 total
25 Jan - 26 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Very clean room, breakfast was delicious and parking was safe On thing that bothered me though… I visited the gym three days in a row and all three days there were no wipes for the machines and nothing to clean the machines with. It a post-covid world that is not acceptable.

Reviewed on 17 Dec 2025

Crowne Plaza Annapolis by IHG
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.

What to do 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.