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Vacation rentals in Maryland

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Top-rated vacation rentals in Maryland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Fixins Farm
SUPERHOST
Entire guest suite · 4 guests · 2 beds · 1 bath

Fixins FarmThis quiet country setting is the perfect jump-off point for your winery & brewery tours. With 5 wineries & 2 breweries within 10 miles, "Fixins Farm" is the perfect 'adults only' weekend getaway spot secluded from all the city stress. Relax in the hot tub, sit on the porch & enjoy the views, take a dip in the pool, sit in the flower garden or enjoy our picnic area & hammock. Be sure to follow us on Instagram (fixinsfarmairbnb) PLEASE NOTE that we do not accommodate children.

Spacious and private waterfront, sleeps 10
SUPERHOST
Entire house · 10 guests · 6 beds · 2 baths

Spacious and private waterfront, sleeps 10Are you looking for a family getaway or a peaceful location to telework? This property offers it all. Tastefully remodeled in 2019 waterfront property with a large private salt water pool, dock for fishing, crabbing and kayaking. One-floor open plan with two large decks. Great for entertainment in privacy and is in proximity to restaurants, vineyards, beautiful beaches and parks of Chesapeake Bay and Patuxent River. Just 1 hour to the south of Washington DC and within minutes to NavAir base.

Wanderlust at Eden-A Charming Destination Retreat
SUPERHOST
Entire guest suite · 4 guests · 2 beds · 1 bath

Wanderlust at Eden-A Charming Destination RetreatOur guest suite in Eden Maryland, is centrally located on the Delmarva Peninsula in the prestigious, established neighborhood of Chesapeake Acres. Ten minutes south of Salisbury, 45ish minutes to Ocean City and Assateague and 25 minutes to the Eastern Shore Of Virginia. Why stay in a yucky hotel when you can have so many amenities and so much privacy?! We assure you’ll have a beautiful, peaceful stay here, and FUN! At 1500 sq. feet there’s plenty of room for kids and critters to move around.

Vacation rentals for every style

Get the amount of space that is right for you

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Popular amenities for Maryland vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Maryland

SUPERHOST
  1. Entire apartment
  2. Baltimore
Perfect for Tourists, Parents and Business Travel
$45 per night
SUPERHOST
  1. Entire apartment
  2. California
Our Little Piece of Heaven
$128 per night
  1. Private room
  2. Forest Hill
Nice room in Nice location
$55 per night
SUPERHOST
  1. Entire house
  2. Glen Burnie
Secluded acre near BWI and Baltimore
$86 per night
SUPERHOST
  1. Tiny house
  2. Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
$72 per night
SUPERHOST
  1. Entire apartment
  2. North Beach
Bayside Oasis of Southern Maryland
$101 per night
SUPERHOST
  1. Entire apartment
  2. Reisterstown
Barn Apt on Tranquil Historic Farm--Amazing Views
$129 per night
SUPERHOST
  1. Entire condominium
  2. Baltimore
Cozy Private Condo in Mt. Vernon w/ Rooftop
$55 per night
SUPERHOST
  1. Entire cottage
  2. Lusby
Gettin to the point. ( Cove Point Beach)
$145 per night
  1. Farm stay
  2. Chestertown
Blue Heron Farm Waterfront Chalet
$286 per night
SUPERHOST
  1. Entire cottage
  2. Westover
Heaven on the Bay - A Peaceful Waterfront Retreat
$199 per night
SUPERHOST
  1. Entire loft
  2. Lusby
Beaches, Hiking, Vineyards, Sunset, Fossil Hunting
$99 per night

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.

How do I get around Maryland?

Maryland’s main airport, Baltimore/Washington International Thurgood Marshall (BWI), is a major East Coast hub serving destinations and airlines all over the country and the world. However, the other National Capital Region airports, Reagan National (DCA) and Dulles International (IAD), also provide easy access to many parts of the state. All have ample car rental options. For most destinations outside the National Capital Region, having a car is useful. Within the Region and Baltimore, public transportation makes a car unnecessary, and even difficult. The high-speed Acela train serves Washington D.C. and Baltimore’s BWI airport and Penn Station, and standard Amtrak trains connect those stations to cities all over the region and country. Other parts of the state have train service to nearby regions, including Cumberland in western Maryland.

When is the best time to book a Maryland vacation rental?

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. 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.

What are the 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.