Make way to one of these cities and towns in Maryland for Memorial Day weekend. Enjoy the diverse attractions like family-friendly indoor and outdoor activities, as well as events and parades to honor local and national heroes. Attend a tribute to military members in Rockville, or embark on a tubing adventure on the Wicomico River in Salisbury. Book a stay at one of numerous Maryland vacation rentals for your upcoming Memorial Day trip. Plan your itinerary with these nine cities as your top contenders.

1. Chesapeake City

Welcome summertime with the locals in Chesapeake City by attending the Memorial Day celebration at the Chesapeake Beach Resort and Spa, complete with live entertainment, food, and family-friendly activities. This Maryland city pulls out all the stops to celebrate local heroes with the Stars and Stripes Festival that includes a Vietnam Memorial dedication. Explore this city that joins the Chesapeake and Delaware bays by touring the C and D Canal Museum, or take a Horse Country Tour with Uniglobe Hill Travel before heading back to your cozy vacation rental.

Find vacation rentals near Chesapeake City

2. Rockville

Find adventure for the thrill seekers on your Memorial Day weekend trip with a vacation rental in Rockville, a small Maryland city that offers big attractions. Spend an afternoon fishing at Seneca Creek State Park, or shop away the evening at the specialty shops in the Rockville Town Square. May weather is perfect for a hike on the Rock Creek Trail or a zipline excursion on the Go Ape Treetop Adventure Course. Each year, Rockville hosts the Hometown Holidays festival over Memorial Day weekend that includes a parade, tribute to the armed forces, and live music in the Rockville Town Center.

Find vacation rentals in Rockville

3. Annapolis

The capitol city of Maryland provides plenty of opportunities to learn more about the city’s founding fathers when you stop in at the Thomas Point Shoal Lighthouse, or view the 17th and 18th-century homes in the downtown area. Soak up the warm temperatures in late May while on the Original Annapolis Seafood Crawl, or the Heritage Region Wine Tour. The trails at the Quiet Waters Park give you and your family stunning views of the flowing waters that run through the city. When hunger strikes, indulge in some fresh seafood at the Boatyard Bar and Grill.

Find vacation rentals in Annapolis

Find the perfect Maryland vacation rental on is the world's #1 vacation rental search engine with over 10 million properties!

4. Cumberland

Honor the heroes who served in the military while in Cumberland when you attend the Memorial Day events, which include a service at the Rocky Gap Veterans Ceremony to welcome the arrival of the National Veterans Awareness Ride team. After paying your respects, enjoy the arrival of summertime with a hike to the Sideling Hill Overlook and Rest area to soak in the stunning views. Make a splash when signing up for a river rafting tour with Get Out and Play Outfitters, or opt for a self-guided tour and hike at Rocky Gap State Park.

Find vacation rentals in Cumberland

5. Salisbury

Memorial Day welcomes summer and fun in the sun in Salisbury with access to kayaking or canoeing in the Wicomico River. Grab some rentals from Capital SUP SBY, and float down the river with the family after a vigorous hike on the trails of Schumaker Park. Take advantage of the historical attractions to learn more about the city and the local heroes when viewing the exhibits at Pemberton Historical Park. Wind down in the evening with homemade brews from the Evolution Craft Brewing Company before retiring to your vacation rental.

Find vacation rentals in Salisbury

6. Timonium

Timonium is a mecca for family-friendly entertainment with indoor attractions such as Breakout Games, Kiddie Crusoe, and Earth Treks Climbing Center. Keep the kids active with a day at Sky Zone Trampoline Park, and then opt for some adult-only time at Padonia Ale House. This small Maryland city takes pride in its Memorial Day celebrations with an annual Memorial Day ceremony that includes a 21-gun salute, wreath laying, and music in honor of fallen heroes at the Dulaney Valley Memorial Gardens.

Find vacation rentals near Timonium

7. Bowie

Make Bowie your vacation destination for Memorial Day weekend and treat the family to a day at Six Flags America to ride the coasters. Enjoy the warm breezes that May brings when shopping for fresh veggies at the Bowie’s Farmer’s Market, or walking the trails at Allen Pond Park. Adults can sign up for the city’s Vino 301 Wine Concierge Tour, and the entire family can take part in the special Memorial Day events over the weekend that include the Bowie Memorial Day parade to salute service men and women.

Find vacation rentals in Bowie

8. Baltimore

Head to the big city of Baltimore for a luxurious vacation rental and to take in the special events dedicated to Memorial Day. As the home of the Fort McHenry National Monument, Baltimore pulls out all the stops to honor military members with tours and informative workshops at the Washington Monument. Each year, the city also hosts the SoWeBo Arts Festival over Memorial Day weekend. This festival on Hollins Street offers live entertainment, demonstrations by local artists and fashion designers, and opportunities for the kids to see carnival acts, and puppet shows. Continue to entertain the little ones with a stop in at the National Aquarium to see underwater creatures.

Find vacation rentals in Baltimore

9. Hagerstown

Immerse yourself in the historical city of Hagerstown, and spend your Memorial Day holiday touring the Price-Miller House Museum or shopping at the Pennsylvania Dutch Market. The warm temperatures in late May are ideal for dipping your feet into the canal at the Chesapeake and Ohio Canal National Historic Park, or relaxing on the grounds of the Olney Winery. Treat the kids to a day at the Discovery Station before heading back to your rustic cabin or luxurious vacation rental for an evening bonding with the family.

Find vacation rentals in Hagerstown

Ready to go? Check out these amazing Maryland vacation rentals on