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Vacation rentals in Maryland

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Top-rated vacation rentals in Maryland

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

Guest favorite
Guesthouse in Myersville
Spruce Run Cottage, Farm stay on Catoctin Mountain
The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.
May 5 – 12
$80 per night
Guest favorite
Guesthouse in Fort Washington
Urban Cottage,MD minutes from DC/National Harbor
Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.
Jul 19 – 26
$182 per night
Guest favorite
Guesthouse in Easton
Chill in The Crib! Easton, Maryland
Welcome to Maryland's Eastern Shore and your own private space in a converted corn crib, complete with the comforts of home. The space includes a vaulted ceiling, queen-sized Casper® mattress, quality linens, heat & AC, wireless Internet, a coffee counter, stocked bar fridge, full bath w/ shower (includes quality bath supplies), and a private entrance. Our space is permitted for two individuals (No children under 8 years of age.), and please limit your visit to one vehicle only.
Sep 28 – Oct 3
$125 per night

Popular amenities for Maryland vacation rentals

Maryland waterfront vacation rentals

Guest favorite
Guesthouse in Lusby
Cozy Lakeside Studio Retreat.
May 17 – 24
$113 per night
Guest favorite
Cabin in Myersville
Cabin on Middle Creek - Myersville MD - Middletown
Sep 2 – 9
$98 per night
Guest favorite
Home in Cambridge
"Happy Campers" Waterfront Apartment!
Feb 15 – 22
$135 per night
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
Nov 6 – 13
$200 per night
Guest favorite
Cabin in Lusby
Hideaway on the Bay: Waterfront Vintage A Frame
Jun 21 – 28
$283 per night
Guest favorite
Home in Shady Side
Luxe Modern Chesapeake Waterfront Oasis
Aug 28 – Sep 4
$621 per night
Guest favorite
Cottage in Westover
Rumbley Cottage on the Tangier Sound-Private Beach
Mar 2 – 9
$279 per night
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
Feb 6 – 13
$166 per night
Guest favorite
Townhouse in Ocean City
Edgewater Escape - Bayfront Condo w/Private Porch
Jun 21 – 28
$500 per night
Guest favorite
Cottage in Saint Michaels
La Casita on Harris Creek, St. Michaels
Mar 28 – Apr 4
$436 per night
Guest favorite
Home in Lusby
Coastal Oasis On The Chesapeake, King Bd sleeps 12
Aug 14 – 21
$460 per night
Guest favorite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
Nov 10 – 17
$136 per night

Maryland fishing vacation rentals

Superhost
Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
May 22 – 29
$77 per night
Guest favorite
Guest suite in Lusby
Riverfront Chalet Kayak/Canoe, pier, breakfast!
Feb 3 – 10
$116 per night
Guest favorite
Apartment in Pasadena
Sea Dreamer aka Phenomenal Hospitality
Oct 16 – 23
$83 per night
Guest favorite
Guest suite in Berlin
Ayers Creek Carriage House
Apr 9 – 16
$110 per night
Guest favorite
Cabin in Lusby
Peaceful Waterfront Retreat on The Bay
Oct 12 – 19
$143 per night
Guest favorite
Cottage in Edgewater
Waterfront Chesapeake Bay Getaway Firepit & Pier!
Aug 20 – 27
$283 per night
Guest favorite
Cottage in Cambridge
Church Creek - waterfront cottage & pool - private
Jan 5 – 12
$192 per night
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
Mar 5 – 12
$98 per night
Guest favorite
Home in Annapolis
Cape St Claire waterfront getaway
Sep 4 – 11
$126 per night
Guest favorite
Home in Cambridge
Guest House: Farm homestead
Apr 5 – 12
$109 per night
Guest favorite
Guesthouse in Westminster
The Pig Shed Writer’s Retreat at Barter Lady Farm
Mar 24 – 31
$89 per night
Guest favorite
Cabin in North East
Waterfront Cabin on the Chesapeake
Dec 18 – 25
$327 per night

Home rentals in Maryland

Guest favorite
Home in Myersville
The Crooked Cottage: a Cozy, Curated Escape
Jun 9 – 16
$145 per night
Guest favorite
Home in Tracys Landing
The Little Gypsy BoHome
Jul 12 – 19
$700 per night
Guest favorite
Home in Silver Spring
Quiet, Modern Apartment - Metro Accessible.
Nov 28 – Dec 5
$59 per night
Guest favorite
Home in Rock Hall
Bayside Beach House
Mar 17 – 24
$136 per night
Guest favorite
Home in Lexington Park
Private beach retreat in historic St. Mary's City
Jun 12 – 19
$450 per night
Superhost
Home in Annapolis
Spacious 3BR 2Bath Minutes from Downtown Annapolis
Mar 20 – 27
$82 per night
Guest favorite
Home in Silver Spring
Cozy One Bedroom Apartment Near DC
May 1 – 8
$70 per night
Guest favorite
Home in Silver Spring
Entire Guest Suite/Apt in Silver Spring
Apr 30 – May 7
$86 per night
Guest favorite
Home in Swanton
Bev's House at Sunny Meadows
Jul 25 – Aug 1
$148 per night
Guest favorite
Home in Lusby
Historic Rousby Hall, Waterfront, Patuxent River
Apr 2 – 9
$611 per night
Guest favorite
Home in Chestertown
CHESAPEAKE SUNSETS
Apr 13 – 20
$170 per night
Guest favorite
Home in Cambridge
Sunset Breezes - quiet waterfront retreat
Mar 14 – 21
$258 per night

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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