Vacation rentals in Maryland

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Popular amenities for Maryland vacation rentals

Maryland waterfront vacation rentals

Guest favorite

Guesthouse in White Marsh

4.97 out of 5 average rating, 140 reviews

Bird River Bottega - A Waterfront Oasis!

Jan 13 – 20

R1,712 ZAR per night
Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 301 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Aug 23 – 30

R2,544 ZAR per night
Guest favorite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 263 reviews

The Crab House - a Private, Waterfront Guest House

Jan 15 – 22

R4,465 ZAR per night
Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 547 reviews

Sea Dreamer aka Phenomenal Hospitality

Oct 3 – 10

R1,793 ZAR per night
Guest favorite

Cabin in Lusby

4.91 out of 5 average rating, 208 reviews

Peaceful Waterfront Retreat on The Bay

Oct 20 – 27

R3,038 ZAR per night
Guest favorite

Guesthouse in Bushwood

4.92 out of 5 average rating, 143 reviews

Little House by the water

Mar 14 – 21

R1,694 ZAR per night
Guest favorite

Guest suite in Chestertown

4.99 out of 5 average rating, 191 reviews

Beautiful Waterfront Chestertown Getaway

Oct 1 – 8

R2,663 ZAR per night
Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 104 reviews

Coastal Waterfront 1 Bedroom Cottage

Nov 6 – 13

R7,056 ZAR per night

Maryland fishing vacation rentals

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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