
Maryland Vacation Packages
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Top places to visit in Maryland
Best Maryland Package Vacations
With the vast Chesapeake Bay stretching all the way to the Appalachian Mountains, and Deep Creek Lake providing the very best in outdoor adventures, vacations in Maryland have something for the whole family. Discover Baltimore’s food scene, learn to sail in the bay or try an adventure sport for some serious family fun. Read our travel guide to discover the best places for Maryland vacations.
Why Vacation in Maryland?
Vacations in Maryland will make you fall in love with the eastern shore way of life. Hang out at an Inner Harbor crab shack in Baltimore or explore the region’s historical legacy in Annapolis.
Must-See Maryland Attractions
Inner Harbor, Baltimore
Maryland vacations should always include a trip to Inner Harbor, the best place for sightseeing in Baltimore. This historic port offers vacationers divine seafood, century-old naval ships at the National Aquarium, and spectacular views on the 27th floor of the Baltimore World Trade Center.
Fort McHenry, Baltimore
The inspiration for the Star-Spangled Banner, this pentagonal fort played a notable role in the war of 1812. Now a national park, Fort McHenry is the ideal place to explore Maryland’s wavering past.
Rocky Gap State Park
Right on the border with Pennsylvania, Rocky Gap offers Maryland package vacations for those who love the great outdoors. From hiking to canoeing, families will find undulating and intriguing landscapes to explore at their own pace.
Top Vacation Destinations in Maryland
1. Columbia - Voted one of the best places to live in the US, Columbia has lots of vacation spots to enjoy. Boasting play parks and family-friendly hikes, the surrounding area is built for family fun. With good shopping and excellent restaurants, everything you need for your vacation in Maryland is right here.
2. Ocean City - One of the top Maryland destinations, Ocean City is the ultimate seaside vacation. Relax on sandy beaches or try your hand at kayaking. Kids will love the amusement parks and boardwalk entertainment, and there are plenty of vacation rentals to make the most of.
3. Baltimore - A city that perfectly blends history with modernity, Baltimore strikes a great balance for vacationers. Couples will love Fells Point with its taverns and seafood eateries, while families should make a beeline for the Port Discovery Children’s Museum and the Maryland Zoo.
4. Berlin - A little outside Ocean City, Berlin is a wonderful place for a day trip or a whole vacation. Filled with independent shops and a friendly community vibe, visitors are welcomed with open arms. Visit the nearby Frontier Town amusement park if you’re traveling with children.
5. Deep Creek Lake - A perfect place for a family vacation, Deep Creek Lake is Maryland’s largest lake and has everything from fishing and bird-watching to boating and rafting. Here you can see some more of Maryland’s spectacular scenery at Swallow Falls State Park.
Best Time To Visit Maryland
With so much to do, Maryland vacations can be enjoyed any time of year. Ocean City and the Chesapeake Bay are best visited in the warm summer months, while National Harbor is best enjoyed in winter. Wisp Resort in Garrett County is excellent for skiing, making Maryland a great choice for adrenaline-junkies and families alike.
Getting Around Maryland
Maryland is well connected by air and road. Fly into Baltimore, Washington, VA or Philadelphia and hire a car to continue your Maryland vacation. With plenty of major roads and highways, it’s fast and easy to get around Maryland.
Top Maryland vacation package deals

Graduate by Hilton Annapolis
Nov 14 - Nov 16
Boston (BOS) to Baltimore (BWI)
Baltimore (BWI) to Boston (BOS)
Reviewed on Apr 19, 2025

Kellogg Conference Hotel at Gallaudet University
Nov 9 - Nov 16
Boston (BOS) to Washington (DCA)
Reviewed on Apr 24, 2023

The Royal Sonesta Washington DC Dupont Circle
Nov 9 - Nov 16
Boston (BOS) to Washington (WAS)
Reviewed on May 27, 2025

Tysons Corner Marriott
Nov 6 - Nov 11
Boston (BOS) to Washington (DCA)
Reviewed on Jun 12, 2025

Homewood Suites by Hilton Arlington Rosslyn Key Bridge
Nov 9 - Nov 16
Boston (BOS) to Washington (DCA)
Reviewed on May 28, 2025
Top rated hotels for your Maryland vacation package

Renaissance Baltimore Harborplace Hotel

Hyatt Place Ocean City / Oceanfront

Grand Hotel Ocean City Oceanfront
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- Rock Hall Harbor
- Six Flags America
- Glen Burnie Vacations
- Linthicum Heights Vacations
- Bingo World
- Chesapeake Beach Vacations
- Pasadena Vacations
- Kunta Kinte–Alex Haley Memorial
- Grasonville Vacations
- Maryland Live Casino
- Stevensville Vacations
- Dundalk Vacations
- Arundel Mills Mall
- Lanham Vacations
- Chesapeake Bay Bridge
- Severn Vacations
- St. Michaels Vacations
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- Queenstown Harbor Golf Club
- Bowie Vacations
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- Annapolis Mall Shopping Center
- Harmans Vacations
- Jessup Vacations
- Rock Hall Vacations
- Banneker Douglass Museum
- Maryland World War II Memorial
- Hanover Vacations
- Upper Marlboro Vacations
- Rocky Point Golf Course