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
Guesthouse in White Marsh
4.97 out of 5 average rating, 140 reviewsBird River Bottega - A Waterfront Oasis!
Jan 13 – 20
Guest suite in Lusby
4.99 out of 5 average rating, 301 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
Aug 23 – 30
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 263 reviewsThe Crab House - a Private, Waterfront Guest House
Jan 15 – 22
Apartment in Pasadena
4.99 out of 5 average rating, 547 reviewsSea Dreamer aka Phenomenal Hospitality
Oct 3 – 10
Cabin in Lusby
4.91 out of 5 average rating, 208 reviewsPeaceful Waterfront Retreat on The Bay
Oct 20 – 27
Guesthouse in Bushwood
4.92 out of 5 average rating, 143 reviewsLittle House by the water
Mar 14 – 21
Guest suite in Chestertown
4.99 out of 5 average rating, 191 reviewsBeautiful Waterfront Chestertown Getaway
Oct 1 – 8
Guesthouse in Annapolis
4.99 out of 5 average rating, 104 reviewsCoastal Waterfront 1 Bedroom Cottage
Nov 6 – 13
Maryland fishing vacation rentals
Home in Annapolis
4.99 out of 5 average rating, 197 reviewsCape St Claire waterfront getaway
Nov 13 – 20
Tiny home in Cambridge
4.89 out of 5 average rating, 497 reviewsBlackwater Tiny Cabin on Snakehead Creek
Aug 5 – 12
Home in Cambridge
4.92 out of 5 average rating, 178 reviewsGuest House: Farm homestead
Jul 27 – Aug 3
Guesthouse in Riva
4.99 out of 5 average rating, 273 reviewsThe Riva House
Oct 18 – 25
Bungalow in Deale
4.86 out of 5 average rating, 355 reviewsCozy waterfront getaway on the Bay
Feb 6 – 13
Guest suite in Arnold
4.84 out of 5 average rating, 496 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
Jun 26 – Jul 3
Guest suite in Piney Point
4.94 out of 5 average rating, 224 reviewsSpectacular beachfront walk-out in Piney Point MD
Sep 15 – 22
Cabin in Lusby
4.94 out of 5 average rating, 142 reviewsHideaway on the Bay: Waterfront Vintage A Frame
Jun 10 – 17
Home rentals in Maryland
Home in Myersville
4.97 out of 5 average rating, 145 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Jul 22 – 29
Home in Annapolis
4.96 out of 5 average rating, 108 reviewsHistoric Downtown in-law suite
Mar 20 – 27
Home in Silver Spring
4.99 out of 5 average rating, 149 reviewsEntire Guest Suite/Apt in Silver Spring
Dec 24 – 31
Home in Shady Side
5.0 out of 5 average rating, 116 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Jan 28 – Feb 4
Home in Chestertown
4.94 out of 5 average rating, 128 reviewsCHESAPEAKE SUNSETS
Apr 19 – 26
Home in North East
4.9 out of 5 average rating, 122 reviewsPrivate home
Dec 1 – 8
Home in Swanton
4.97 out of 5 average rating, 186 reviewsBev's House at Sunny Meadows
May 29 – Jun 5
Home in Lusby
5.0 out of 5 average rating, 111 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Oct 27 – Nov 3
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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