Highland Beach Holidays
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Highland Beach Holiday
Our pick of the best Highland Beach Hotel Deals
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,885 reviews)
Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!
Reviewed on 31 Jan 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NZ$157 per night from 22 Feb to 23 Feb
NZ$157
22 Feb - 23 Feb
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
Room was spotless. Staff was very courteous. Would highly recommended.
Reviewed on 5 Feb 2026
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
The price is NZ$301 per night from 23 Feb to 24 Feb
NZ$301
23 Feb - 24 Feb
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
Room was clean. Beds were comfy. Very walkable to all of the hot spots. Parking was expensive onsite.
Reviewed on 4 Feb 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(3 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
5/5(1 review)
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.
Anne Arundel Medical Center
If Anne Arundel Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Parole.
What to do in Highland Beach
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
NZ$70
per adult
Ashes and Apparitions of Annapolis Ghost Tour
NZ$56
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
