Vacation rentals in Maryland
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Top-rated vacation rentals in Maryland
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Popular amenities for Maryland vacation rentals
Maryland waterfront vacation rentals
Guesthouse in Stevensville
5.0 out of 5 average rating, 219 reviewsWaterfront Getaway - View of bay from your bed
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 301 reviewsHistoric St.Mary's City at the Lazy Bear Cottage
Guesthouse in White Marsh
4.97 out of 5 average rating, 146 reviewsBird River Bottega - A Waterfront Oasis!
Cabin in Myersville
4.97 out of 5 average rating, 261 reviewsCabin on Middle Creek - Myersville MD - Middletown
Guesthouse in Annapolis
4.99 out of 5 average rating, 111 reviewsCoastal Waterfront 1 Bedroom Cottage
Cottage in Saint Michaels
4.98 out of 5 average rating, 142 reviewsLa Casita on Harris Creek, St. Michaels
Guest suite in Chestertown
4.99 out of 5 average rating, 194 reviewsBeautiful Waterfront Chestertown Getaway
Cottage in Westover
4.99 out of 5 average rating, 185 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Home rentals in Maryland
Home in Myersville
4.97 out of 5 average rating, 159 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Home in Cambridge
4.93 out of 5 average rating, 187 reviewsGuest House: Farm homestead
Home in Annapolis
4.96 out of 5 average rating, 116 reviewsHistoric Downtown in-law suite
Home in Shady Side
5.0 out of 5 average rating, 124 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Home in Annapolis
5.0 out of 5 average rating, 109 reviewsLuxury Waterfront Annapolis/ Private Beach & Dock
Home in Annapolis
5.0 out of 5 average rating, 201 reviewsCape St Claire waterfront getaway
Home in North Beach
5.0 out of 5 average rating, 100 reviewsWaterfront, Dog-friendly, Hot Tub, Peleton, Bikes
Home in Lusby
5.0 out of 5 average rating, 114 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Maryland fishing vacation rentals
Tiny home in Cambridge
4.88 out of 5 average rating, 510 reviewsBlackwater Tiny Cabin on Snakehead Creek
Guest suite in Arnold
4.96 out of 5 average rating, 577 reviewsOld Bay Bungalow
Guesthouse in Westminster
4.87 out of 5 average rating, 284 reviewsThe Pig Shed Writer’s Retreat at Barter Lady Farm
Cabin in Lusby
4.94 out of 5 average rating, 151 reviewsHideaway on the Bay: Waterfront Vintage A Frame
Guest suite in Piney Point
4.94 out of 5 average rating, 229 reviewsSpectacular beachfront walk-out in Piney Point MD
Guest suite in Tilghman Island
4.97 out of 5 average rating, 116 reviewsBlack Walnut Cove Retreat, Tilghman Island
Cottage in Edgewater
4.99 out of 5 average rating, 132 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Guest suite in Berlin
4.97 out of 5 average rating, 541 reviewsAyers Creek Carriage 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.
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