Vacation rentals in Maryland
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Top-rated vacation rentals in Maryland
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Vacation rentals for every style
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Popular amenities for Maryland vacation rentals
Maryland waterfront vacation rentals
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
Guesthouse in Stevensville
Waterfront Getaway - View of bay from your bed
Guesthouse in Lusby
Cozy Lakeside Studio Retreat.
Cabin in Myersville
Cabin on Middle Creek - Myersville MD - Middletown
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Cabin in Lusby
Peaceful Waterfront Retreat on The Bay
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
Maryland fishing vacation rentals
Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
Home in Cambridge
Guest House: Farm homestead
Cabin in Lusby
Hideaway on the Bay: Waterfront Vintage A Frame
Home in Annapolis
Cape St Claire waterfront getaway
Cottage in Westover
Rumbley Cottage on the Tangier Sound-Private Beach
Guesthouse in Westminster
The Pig Shed Writer’s Retreat at Barter Lady Farm
Guest suite in Piney Point
Spectacular beachfront walk-out in Piney Point MD
Home in Sharpsburg
Charming Historic Canal House C&O Potomac Antietam
Home rentals in Maryland
Home in Silver Spring
Entire Guest Suite/Apt in Silver Spring/FDA
Home in Annapolis
Historic Downtown in-law suite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis - 5 Star
Home in Lusby
Historic Rousby Hall, Waterfront, Patuxent River
Home in Silver Spring
Quiet, Modern Apartment - Metro Accessible.
Home in Lusby
Cove Point Beach Cabin
Home in Swanton
Bev's House at Sunny Meadows
Home in Rock Hall
Bayside Beach House
Your guide to Maryland
Welcome to Maryland
Maryland’s 3,190 miles of shoreline and long riverfronts shape its natural appeal with sandy stretches and stellar sunrises. Charming old towns boast beautiful views and relaxing beaches as well as a healthy dose of American history, be it the origins of the national anthem or the Battle of Antietam. Though Annapolis is the state’s political capital, Baltimore is much larger, and both take many cultural and political cues from being a part of the National Capital Region and their proximity to Washington D.C. Many of the state’s claims to fame come from Chesapeake Bay, the water that nearly splits the eastern part of Maryland in two. From there we get the famed Maryland crab and other seafood that drive the local cuisine; the naval and civilian boating culture of Annapolis; and, of course, the scenic byways that weave across the water.
The best time to stay in a vacation rental in Maryland
Most of Maryland experiences four classic seasons, with chilly, snowy winters and hot, humid summers. At the Chesapeake Bay beaches, the hot, humid summers are more tolerable, making it a big draw for people looking to cool off on their vacation. But for most of the state, late spring and early fall bring the most comfortable weather. Spring in Maryland brings out the blooms, and various cherry blossom and garden events lure visitors to admire the bright colors, while fall shows its own red, orange, and brown hues. Though western Maryland stays cooler year-round, the higher elevations receive more snow in winter, which attracts snowshoers and other winter sports enthusiasts. But even the eastern part of the state can see significant snowfall, resulting in cold, icy conditions that are best suited for exploring indoor attractions.
Top things to do in Maryland
Cambridge
The small Eastern Shore town of Cambridge merges many of Maryland’s most iconic features. You can get a taste of history — it’s one of the oldest colonial towns in the country, just 15 minutes from the Harriet Tubman Underground Railroad Visitor Center — as well as a taste of the local seafood at the many crab restaurants overlooking Chesapeake Bay as you wander the boardwalk, or at Sailwinds Park.
Baltimore Inner Harbor
The focal point of Maryland’s largest city, this historic seaport and repurposed industrial area holds a slew of history and tons of museums. The National Aquarium, Port Discovery Children’s Museum, and the Reginald F. Lewis Museum of Maryland African American History and Culture will keep you busy all day, along with the area’s many restaurants and bars.
Assateague Island National Seashore
The peaceful, sandy beaches and windswept salt marshes of this 37-mile barrier island on Maryland’s far eastern Atlantic shores would be enough to make it an ideal destination. But it’s the beautiful herd of wild horses for which it’s most famous.
Destinations to explore
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- Monthly Rentals Maryland
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