Highland Beach Packages (Flight + Hotel)
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ฿4,531 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
Top hotels in Highland Beach
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is ฿2,347 per night from 4 Jan to 5 Jan
฿2,347
฿2,676 total
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
did not dine in your hotel.
Reviewed on 24 Dec 2025
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,895 reviews)
Best place to stay is the main building
Reviewed on 22 Dec 2025
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
The price is ฿3,460 per night from 4 Jan to 5 Jan
฿3,460
฿3,945 total
4 Jan - 5 Jan 2026
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
Yes!
Reviewed on 27 Dec 2025
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
U.S. Naval Academy
4.5/5(5 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
Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.
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: Historical Treasures of the City with Self-Guided Audio Tour
฿312
per traveller
80% of travellers recommend
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
฿953
per adult
Ashes and Apparitions of Annapolis Ghost Tour
฿914
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.
