Maryland vacation rentals

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Popular amenities for Maryland vacation rentals

Maryland waterfront vacation rentals

Guest favorite
Guesthouse in Stevensville
Waterfront Getaway - View of bay from your bed
Nov 25 – Dec 2
$246 per night
5.0 out of 5 average rating, 201 reviews
Guest favorite
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
Oct 2 – 9
$72 per night
4.98 out of 5 average rating, 292 reviews
Guest favorite
Cabin in Myersville
Cabin on Middle Creek - Myersville MD - Middletown
Nov 2 – 9
$98 per night
4.97 out of 5 average rating, 247 reviews
Guest favorite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis
Nov 24 – Dec 1
$631 per night
5.0 out of 5 average rating, 109 reviews
Guest favorite
Cottage in Westover
Rumbley Cottage on the Tangier Sound-Private Beach
Dec 18 – 25
$295 per night
4.99 out of 5 average rating, 178 reviews
Superhost
Bungalow in Deale
Cozy waterfront getaway on the Bay
Nov 4 – 11
$152 per night
4.86 out of 5 average rating, 352 reviews
Guest favorite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
Jul 21 – 28
$489 per night
4.99 out of 5 average rating, 135 reviews
Guest favorite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
Mar 25 – Apr 1
$758 per night
5.0 out of 5 average rating, 103 reviews

Maryland fishing vacation rentals

Superhost
Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
Jun 11 – 18
$73 per night
4.89 out of 5 average rating, 491 reviews
Guest favorite
Home in Annapolis
Cape St Claire waterfront getaway
Aug 11 – 18
$126 per night
4.99 out of 5 average rating, 195 reviews
Guest favorite
Apartment in Pasadena
Sea Dreamer aka Phenomenal Hospitality
Nov 30 – Dec 7
$83 per night
4.99 out of 5 average rating, 539 reviews
Guest favorite
Townhouse in Port Deposit
Quarry Landing *River View* in Port Deposit
$88 per night
4.96 out of 5 average rating, 143 reviews
Guest favorite
Home in Lusby
Coastal Oasis On The Chesapeake, King Bd sleeps 12
Jul 31 – Aug 7
$460 per night
4.99 out of 5 average rating, 111 reviews
Guest favorite
Home in Sharpsburg
Charming Historic Canal House C&O Potomac Antietam
Jul 18 – 25
$172 per night
4.99 out of 5 average rating, 106 reviews
Guest favorite
Guesthouse in Riva
The Riva House
Feb 25 – Mar 4
$136 per night
4.99 out of 5 average rating, 273 reviews
Guest favorite
Cottage in Edgewater
Waterfront Chesapeake Bay Getaway Firepit & Pier!
Nov 18 – 25
$279 per night
4.99 out of 5 average rating, 118 reviews

Home rentals in Maryland

Guest favorite
Home in Annapolis
Historic Downtown in-law suite
Feb 3 – 10
$106 per night
4.96 out of 5 average rating, 98 reviews
Guest favorite
Home in Lusby
Historic Rousby Hall, Waterfront, Patuxent River
Apr 4 – 11
$611 per night
5.0 out of 5 average rating, 110 reviews
Guest favorite
Home in Myersville
The Crooked Cottage: a Cozy, Curated Escape
Aug 28 – Sep 4
$145 per night
4.96 out of 5 average rating, 141 reviews
Guest favorite
Home in Tracys Landing
The Little Gypsy BoHome
Feb 3 – 10
$600 per night
4.99 out of 5 average rating, 162 reviews
Guest favorite
Home in Silver Spring
Entire Guest Suite/Apt in Silver Spring
May 23 – 30
$88 per night
4.99 out of 5 average rating, 144 reviews
Guest favorite
Home in Kent Narrows
Chester Riverfront At Kent Narrows
Apr 7 – 14
$241 per night
5.0 out of 5 average rating, 275 reviews
Guest favorite
Home in New Market
Historic Peace and Plenty Farm: Pool House
Oct 6 – 13
$225 per night
4.94 out of 5 average rating, 111 reviews
Guest favorite
Home in Silver Spring
Cozy One Bedroom Apartment Near DC
Mar 28 – Apr 4
$73 per night
4.94 out of 5 average rating, 175 reviews

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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