When planning a trip to Maryland, look forward to a relaxing weekend getaway in the midst of parks, lakes, and forests. Staying at one of many incredible Maryland vacation rentals puts you within proximity of gorgeous nature centers in Laurel, the Maryland Mountains in Cumberland, or big city attractions in Baltimore. Spend a weekend exploring the historic city of Hagerstown, or take a dip in the Wicomico River in Salisbury. Make Maryland your vacation destination, and choose one of these eight cities ideal for an unforgettable getaway.

1. Baltimore

Join in the busy vibe of Baltimore with a vacation rental in the big city. This historic Maryland city is known as the economic hub and is home to historic neighborhoods and museums, such as the American Visionary Art Museum and the Fort McHenry National Monument. Families can explore the scenic sites while hiking the trails at Federal Hill Park or snap a photo in front of the Washington Monument. Let the kids see underwater creatures at the National Aquarium before taking in a performance at the Hippodrome Theatre on a weekend evening. Opt for a nightcap at the Sagamore Spirit distillery before retreating to your vacation rental.

Find vacation rentals in Baltimore

2. Rockville

When you want to settle into a cozy vacation rental in a small city, Rockville is the obvious choice for your Maryland weekend getaway. This small town offers big city enthusiasm with attractions ideal for fishing and hunting enthusiasts. Spend the weekend reeling in fish at Seneca Creek State Park or hike the Rock Creek Trail on a Saturday afternoon. Entertain the thrill seekers with a trip to the Earth Treks Climbing Center or find the perfect souvenir while shopping at the Rockville Town Square. Home to Lake Needwood, a Rockville getaway affords you with opportunities to make a splash in the water before ziplining through the trees at the Go Ape Treetop Adventure Course.

Find vacation rentals in Rockville

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

3. Laurel

Opt for a weekend getaway in the midst of wildlife when booking your vacation rental in Laurel. Home to the Patuxent Research Refuge, this city boasts scenic views and opportunities to capture rare species from your balcony. The 19th-century mill town is now home to the Fort Mede Army base and offers history buffs a chance to tour the nearby Montpelier Mansion or hike through Dinosaur Park. Let the kids burn off some energy at ClimbZone, an interactive hotspot with climbing walls for every skill level. Before heading back to your cozy rental, stop in for dinner at Mid Atlantic Seafood or Mango’s Grill Restaurant.

Find vacation rentals in Laurel

4. Annapolis

When you make your vacation destination in Maryland’s capital, plan to see 17th and 18th-century homes from the city’s founding fathers. Make a stop at the Thomas Point Shoal Light for spectacular views of the flowing waters or hike the trails at Quiet Waters Park. Time your weekend getaway to coincide with the tours sponsored by the city, including the Heritage Region Wine Tour, the Original Annapolis Seafood Crawl, or the Heart of Annapolis sightseeing adventure. Take a peaceful walk through the William Paca Garden before diving into a seafood dinner at Boatyard Bar and Grill or Carrol’s Creek Cafe.

Find vacation rentals in Annapolis

5. Cumberland

Indulge the nature enthusiasts with a vacation rental nestled in the Maryland Mountains. Cumberland is known for its tree-lined streets and access to the trails at Rocky Gap State Park. Spend a day exploring the Western Maryland Scenic Railroad, complete with rides for the kids and historic artifacts, or venture out to the Sideling Hill Overlook and Rest Area for a family photo and breathtaking views. When making Cumberland your vacation destination during the warmer months, opt for a river rafting tour with Get Out and Play! Outfitters.

Find vacation rentals in Cumberland

6. Salisbury

For gorgeous views of the Wicomico River, make Salisbury your destination for the weekend. As one of the largest Maryland cities on the peninsula, this area is known for its water attractions. Kayak or canoe the river with rentals from Capital SUP SBY or take in the tree-lined trails of Schumaker Park. The Salisbury Zoo puts you close to exotic animals while Pemberton Historical Park showcases the historical significance of this Maryland City. Spend an evening winding down when enjoying cold beverages from the Evolution Craft Brewing Company.

Find vacation rentals in Salisbury

7. Hagerstown

Hagerstown is the ideal city for a weekend getaway when you want to immerse yourself in a historic county. Opt for a tour of the Price-Miller House Museum that dates back to 1825 or feeds the ducks at the Hagerstown City Park. For a family-friendly attraction, let the kids explore the hands-on exhibits at the Discovery Station at Hagerstown or take a ride through the canal at the Chesapeake and Ohio Canal National Historical Park. Shoppers flock to the Pennsylvania Dutch Market to pick up handmade crafts and gifts while the wine enthusiasts enjoy relaxing at Olney Winery and Cool Ridge Vineyard on the weekend.

Find vacation rentals in Hagerstown

8. Chesapeake City

When you want to escape the big city but still have access to Wilmington, Philadelphia, or Baltimore, make Chesapeake City your weekend getaway hotspot. Known as a city with historical value, you can spend your weekend learning about the canal that joins the Delaware and Chesapeake bays at the C and D Canal Museum, or see the thoroughbred horse farms on a Horse Country Tour hosted by Uniglobe Hill Travel. Enjoy the beauty of the canals with a canoe excursion at Lums Pond State Park before making your way back to your Maryland vacation rental.

Find vacation rentals near Chesapeake City


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