Highland Beach Holidays
Book a Hotel + Flight or Car together to unlock savings
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 3.179.721 ₫ per night from 24 May to 25 May
3.179.721 ₫
3.624.881 ₫ total
24 May - 25 May
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Hot water was an issue. Lukewarm at best and a few times no hot water. The elevator was dlow and the other elevator was broken.
Reviewed on 26 Apr 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
The price is 3.769.826 ₫ per night from 25 May to 26 May
3.769.826 ₫
5.198.725 ₫ total
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (1,843 reviews)
Very good hotel but too expensive. Parking price was 50$, a rip off. We should have parked with an app. We didn’t expect the surprise in Annapolis. We pay that money in DC or NYC.
Reviewed on 27 Apr 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
The price is 3.345.688 ₫ per night from 5 May to 6 May
3.345.688 ₫
3.814.084 ₫ total
5 May - 6 May
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Room very clean. Air conditioning unit worked but was extremely loud while turning on and off. Didn’t regulate very well. Breakfast was great bar was adequate. Wished it opened earlier than 5. All staff considerate and professional. All greeted us throughout our stay.
Reviewed on 22 Apr 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
Sandy Point State Park
Enjoy a trip to Sandy Point State Park and popular activities such as boating in Annapolis. Stroll along the area's waterfront or simply savour its top-notch restaurants.
Maryland State House
After visiting Maryland State House, make a plan to see the other sights and activities in Annapolis. While you're in the area, stroll along the waterfront.
Hammond-Harwood House
You can browse the exhibits at Hammond-Harwood House, a museum with a story of its own, during your travels to Annapolis. Wander the area's waterfront or simply enjoy one of its top-notch restaurants.
