Highland Beach Holidays
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Top hotels in Highland Beach
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,877 reviews)
Such a cool place to stay! Water pressure wasn’t great but it’s a very old building.
Reviewed on 26 Feb 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is €82 per night from 10 Mar to 11 Mar
€82
10 Mar - 11 Mar
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
The room and the property were clean. My husband and I paid for the breakfast when we made the reservation. We checked in, but didn't receive our breakfast vouchers until the following day.
Reviewed on 2 Mar 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
The price is €106 per night from 5 Mar to 6 Mar
€106
5 Mar - 6 Mar
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Great
Reviewed on 2 Mar 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.
Popular places to visit
Chesapeake Bay Bridge
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.
Sandy Point State Park
Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.
Maryland State House
Appreciate the superb architecture and fascinating history of America’s first peacetime capitol and the oldest state capitol still in legislative use.
What to do in Highland Beach
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
€25
per adult
Annapolis: Historical Treasures of the City with Self-Guided Audio Tour
€8
per traveller
80% of travellers recommend
Awesome Scavenger Hunt: Annapolis Red Bricks & Blue Views
€13
per adult
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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.
