Highland Beach Travel Guide

Tourist Guide

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,790 reviews)
Perfect Inn for our stay
"Stayed at the Historic Inns of Annapolis - Governor Calvert House. The front desk receptionist was friendly and helpful. Check in was easy and efficient. Valet parked the car and due to being centrally located, we didn't use the car for the two days we were in Annapolis. The room was clean and the ..."

Reviewed on 18 Jul. 2025

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Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
The price is AU$272 per night from 3 Aug to 4 Aug
AU$272
3 Aug - 4 Aug
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
9.4/10 Exceptional! (1,014 reviews)
"Great stay! Would come here again."

Reviewed on 14 Jul. 2025

Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
The price is AU$179 per night from 17 Aug to 18 Aug
AU$179
17 Aug - 18 Aug
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.4/10 Very Good! (1,002 reviews)
"Staff was very nice and professional!"

Reviewed on 10 Jul. 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,212 properties in Highland Beach
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.
The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina

Pasadena
Stay at this cottage in Pasadena. Enjoy free WiFi, a garden, and balconies or patios. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.8/10 Exceptional! (294 reviews)
Tiny House
"This tiny house is cute and has a great view of the water! It’s peaceful aside of the noisy generator running at the wedding venue next door. It wasn’t very clean when we arrived. Floors had some piles of sand and appeared to be unswept. Some trash from the previous people was left laying ..."

Reviewed on 10 Jul. 2025

The Heron's Nest at Atlantic Marina
Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star

Annapolis
Stay at this apartment in Annapolis. Enjoy free WiFi, private pools, and a water park. Popular attractions Annapolis City Dock and U.S. Naval Academy Golf Club ...
10/10 Exceptional! (73 reviews)
Beautiful Place
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."

Reviewed on 19 Feb. 2025

Waterfront Oasis of Annapolis Star
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville
Stay at this cottage in Stevensville. Enjoy free WiFi, a sauna, and a garden. Popular attractions Romancoke Wharf County Park and Bodkin Island are located ...
10/10 Exceptional! (48 reviews)
Getting ready for the wedding
"This home was the perfect place for us to calmly relax for a few days before our son’s wedding in Stevensville. The hosts were incredibly thoughtful and accommodating. The house is lovely, tidy, and tastefully decorated. The kitchen is well-equipped, the bedrooms and bathrooms are comfortable, neat ..."

Reviewed on 6 Jul. 2025

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
See all properties in Highland Beach
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 featuring heritage architecture, interior views and military items

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.

U.S. Naval Academy
Chesapeake Bay Bridge

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.

Chesapeake Bay Bridge
Sandy Point State Park

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.

Sandy Point State Park
Maryland Quiet Waters Park featuring a garden

Maryland Quiet Waters Park

Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.

Maryland Quiet Waters Park
Maryland State House showing heritage architecture and an administrative building

Maryland State House

5/5(1 review)

Appreciate the superb architecture and fascinating history of America’s first peacetime capitol and the oldest state capitol still in legislative use.

Maryland State House
William Paca House

William Paca House

Learn about the life and explore the historic home of 18th-century lawyer and signer of the Declaration of Independence, William Paca.

William Paca House

Activities

Food Tour Plate

Historic Annapolis Food Tour

AU$122
per adult
Historic Annapolis Food Tour
Step into the shadows and discover the haunting tales of our city's past.

Haunted Annapolis: Ghosts of the Harbor & Old Town Tour

AU$40
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

AU$61
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
See all activities in Highland Beach