Western Shore of Maryland, MD

Travel Guide

A crowd of people at an indoor event with blue lighting and hanging decorations.
A dragon boat with green and red details on a calm body of water.
A lighthouse named Concord Point Lighthouse with a clear view of the surrounding landscape.
A red lighthouse with a balcony, surrounded by a park with benches and flower beds.
A tall ship docked at a harbor with a city skyline in the background.

Visit big cities such as Baltimore and Annapolis, charming towns and beautiful seaside parks in this region of Maryland.

Western Chesapeake is the unofficial region of Maryland west of the Chesapeake Bay. The region includes the city of Baltimore, Harford County, Baltimore County, Anne Arundel County, Calvert County and Saint Mary's County. Enjoy the cultural offerings of the region’s metropolises and the wild beauty of the Chesapeake Bay.

As the largest city in Maryland, Baltimore is Western Chesapeake’s cultural and commercial hub. See works by Matisse, Picasso and other renowned artists at the Baltimore Museum of Art or enjoy outdoor shopping at Broadway Market. Don't miss Fort McHenry National Monument, where Francis Scott Key saw the flying American flag that inspired him to write the national anthem of the United States, The Star-Spangled Banner.

Visit the picturesque port town of Annapolis, the capital city of Maryland. The Annapolis Maritime Museum gives visitors insight into the maritime history of Chesapeake Bay. Go crabbing off the museum's piers or explore the bay area by kayak. Watch future officers conduct a perfectly synchronized noon formation at the United States Naval Academy, which has a campus in the heart of the city.

Stroll some of the miles of shoreline in Western Chesapeake. Just outside Baltimore, North Point State Park is a serene oceanfront park. Consisting of preserved and farmed land, it is one of the finest examples of tidal marshland in the Chesapeake area. In the southern part of the region, enjoy miles of hiking, biking and equestrian trails at Greenwell State Park. At the head of the Patuxent River, Merkle Wildlife Sanctuary is the resting grounds of thousands of migrating Canadian geese each year.

Rent a car to explore everything Western Chesapeake has to offer, from small oceanfront villages and national parks to large cities. Temperatures in Western Chesapeake are rarely extreme but you can expect hot summers and chilly winters. Summer is peak visitor season.

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $164 total per night from Aug 9 to Aug 10
$164 total
Aug 9 - Aug 10
Total with taxes and fees
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 ...
Historic Inns of Annapolis
Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
20 W Baltimore St Baltimore MD
$129 nightly
The price is $151 total per night from Jul 30 to Jul 31
$151 total
Jul 30 - Jul 31
Total with taxes and fees
Book a stay at this historic hotel in Baltimore. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.4/10 Very Good! (3,111 reviews)
"I loved it from the food to the room will mos def be back"

Reviewed on Jul 29, 2026

Lord Baltimore Hotel
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
$98 nightly
The price is $111 total per night from Aug 2 to Aug 3
$111 total
Aug 2 - Aug 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
DoubleTree by Hilton Hotel Annapolis
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.
Rollingside Guest Suite

Rollingside Guest Suite

Catonsville MD
Stay at this apartment in Catonsville. Enjoy free WiFi, private pools, and a garden. Popular attractions Benjamin Banneker Historical Park & Museum and Patapsco ...
10/10 Exceptional! (74 reviews)
"Enjoyed our stay. We plan to return"

Reviewed on Jul 24, 2026

Rollingside Guest Suite
The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina

Pasadena MD
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! (316 reviews)
"Perfect little cottage for our weekend getaway! We will definitely be back."

Reviewed on Jun 16, 2026

The Heron's Nest at Atlantic Marina
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a garden. Popular attractions Annapolis City Dock and Bay Ridge Beach are ...
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community 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.

Stay near popular Western Shore of Maryland attractions

Cities near Western Shore of Maryland

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