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! (1,832 reviews)
"Stayed for one night; room was nice, easy to access, and located near numerous local attractions."

Reviewed on 18 Sept 2025

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Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
The price is NZ$205 per night from 29 Sept to 30 Sept
NZ$205
29 Sept - 30 Sept
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 ...
8.6/10 Excellent! (1,012 reviews)
"Relaxing"

Reviewed on 16 Sept 2025

DoubleTree by Hilton Hotel Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is NZ$196 per night from 30 Sept to 1 Oct
NZ$196
30 Sept - 1 Oct
includes taxes & fees
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (1,013 reviews)
"No additional comment."

Reviewed on 19 Sept 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,233 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.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.4/10 Exceptional! (116 reviews)
St. Michael’s Charm
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"

Reviewed on 30 June 2025

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis
Stay at this vacation home in Annapolis. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Sandy Point State Park and Bay Hills Golf ...
9.8/10 Exceptional! (36 reviews)
"Beautiful view, great property. Owner was easy to communicate with"

Reviewed on 1 Sept 2025

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat

Grasonville
Stay at this houseboat in Grasonville. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Chesapeake Bay Environmental Center and Paul ...
10/10 Exceptional! (38 reviews)
"Such a unique and lovely spot! Perfect for our weekend getaway. So many small touches that made us feel so welcomed. I didn’t pay attention to the pictures to notice it’s lifted out of the water, but with the wind & rain overnight we were thankful as we still heard the water lapping underneath but ..."

Reviewed on 10 Sept 2025

Cass-N-Reel Luxury Houseboat
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

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

NZ$51
per adult
Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl
Food Tour Plate

Historic Annapolis Food Tour

NZ$137
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

NZ$55
per adult
100% of travellers recommend
Haunted Annapolis: Ghosts of the Harbor & Old Town Tour
See all activities in Highland Beach