Hillsmere Shores
Travel Guide
Visit Hillsmere Shores

DoubleTree by Hilton Hotel Largo/Washington DC
Everything was clean, the staff was friendly and the esthetics were pleasant.
Reviewed on 11 Apr 2026

Graduate by Hilton Annapolis
Outstanding
Reviewed on 11 Apr 2026

Historic Inns of Annapolis
Valet parking is available. I received a bottle of wine as a gift, wow! The room is spacious but dark, there is no window to the outdoors. The window overlooks a closed-in courtyard that looks as it serves as events (weddings?) venue.
Reviewed on 11 Apr 2026

Chesapeake Houseboat Getaway on Kent Island, Maryland
The houseboat was an absolute dream. We loved everything about it and really enjoyed our two night stay. Julia has thought of everything to make your stay comfortable. It was immaculate, well stocked and all the decor was beautiful. We would love to come back.
Reviewed on 2 Apr 2026

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
It’s beautiful place inside and out!
Reviewed on 8 Apr 2026

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
A lovely home just a block from the shops and restaurants on Talbot Street. The rear addition adds generous living space while preserving the charm of the historic house. The screened-in back deck is a great feature for relaxing evenings.Upstairs, the bedroom feels like a second retreat—spacious, ...
Reviewed on 30 Mar 2026
Popular places to visit

U.S. Naval Academy
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.

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.

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.

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.
Things to do

Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl

Annapolis: Historical Treasures of the City with Self-Guided Audio Tour

Awesome Scavenger Hunt: Annapolis Red Bricks & Blue Views

Ashes and Apparitions of Annapolis Ghost Tour


