Maryland vacation rentals

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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
Cabin in Myersville
Cabin on Middle Creek - Myersville MD - Middletown
Park the car & walk across the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Amazing place to unwind, de-stress & get away. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting.
Feb 4 – 11
G$20,600 GYD per night
4.97 out of 5 average rating, 247 reviews
Guest favorite
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.
Oct 2 – 9
G$15,119 GYD per night
4.98 out of 5 average rating, 292 reviews
Guest favorite
Home in Cambridge
"Happy Campers" Waterfront Apartment!
Come and experience a relaxing getaway at our fully furnished, detached waterfront apartment! Happy Campers is located on the Choptank River, surrounded by acres of pristine land! You will enjoy quiet afternoons, whether you choose to lounge on chairs by the water and birdwatch or take a bike ride down the lane to explore quiet back roads and beautiful country scenery! A short 15 minute drive into the town of Cambridge offers unique boutiques and restaurants, sightseeing and Sailwinds Park!
Nov 26 – Dec 3
G$28,348 GYD per night
5.0 out of 5 average rating, 262 reviews

Popular amenities for Maryland vacation rentals

Maryland waterfront vacation rentals

Guest favorite
Cottage in Saint Leonard
Captain Jack's Bay Hideaway
Sep 2 – 9
G$27,640 GYD per night
4.99 out of 5 average rating, 100 reviews
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
Sep 21 – 28
G$41,750 GYD per night
4.94 out of 5 average rating, 256 reviews
Guest favorite
Cabin in Lusby
Peaceful Waterfront Retreat on The Bay
Sep 13 – 20
G$30,751 GYD per night
4.91 out of 5 average rating, 202 reviews
Guest favorite
Guest suite in Lusby
Riverfront Chalet Kayak/Canoe, pier, breakfast!
Oct 6 – 13
G$25,447 GYD per night
4.99 out of 5 average rating, 297 reviews
Guest favorite
Guesthouse in Lusby
Cozy Lakeside Studio Retreat.
Apr 10 – 17
G$23,623 GYD per night
4.97 out of 5 average rating, 130 reviews
Guest favorite
Guesthouse in Bushwood
Little House by the water
Dec 9 – 16
G$16,169 GYD per night
4.92 out of 5 average rating, 142 reviews
Guest favorite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
Jan 30 – Feb 6
G$28,558 GYD per night
4.97 out of 5 average rating, 116 reviews
Guest favorite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
Jun 25 – Jul 2
G$24,406 GYD per night
4.99 out of 5 average rating, 189 reviews
Guest favorite
Guest suite in Berlin
Ayers Creek Carriage House
Aug 27 – Sep 3
G$22,409 GYD per night
4.97 out of 5 average rating, 527 reviews
Guest favorite
Guesthouse in White Marsh
Bird River Bottega - A Waterfront Oasis!
Nov 16 – 23
G$16,550 GYD per night
4.97 out of 5 average rating, 137 reviews
Guest favorite
Apartment in Leonardtown
Stunning Sunsets on Breton Bay, Seaside apartment
Jul 1 – 8
G$26,728 GYD per night
4.98 out of 5 average rating, 118 reviews
Guest favorite
Apartment in Pasadena
Sea Dreamer aka Phenomenal Hospitality
Nov 14 – 21
G$17,355 GYD per night
4.99 out of 5 average rating, 539 reviews

Maryland fishing vacation rentals

Guest favorite
Cabin in Lusby
Hideaway on the Bay: Waterfront Vintage A Frame
Apr 4 – 11
G$48,597 GYD per night
4.93 out of 5 average rating, 136 reviews
Guest favorite
Townhouse in Port Deposit
Quarry Landing *River View* in Port Deposit
G$18,479 GYD per night
4.96 out of 5 average rating, 143 reviews
Superhost
Tiny home in Cambridge
Blackwater Tiny Cabin on Snakehead Creek
Aug 29 – Sep 5
G$16,199 GYD per night
4.89 out of 5 average rating, 491 reviews
Guest favorite
Home in Annapolis
Cape St Claire waterfront getaway
Aug 11 – 18
G$26,458 GYD per night
4.99 out of 5 average rating, 195 reviews
Guest favorite
Home in Cambridge
Guest House: Farm homestead
Aug 30 – Sep 6
G$22,821 GYD per night
4.92 out of 5 average rating, 176 reviews
Guest favorite
Cottage in Westover
Rumbley Cottage on the Tangier Sound-Private Beach
Feb 27 – Mar 6
G$61,946 GYD per night
4.99 out of 5 average rating, 178 reviews
Guest favorite
Guesthouse in Westminster
The Pig Shed Writer’s Retreat at Barter Lady Farm
Sep 3 – 10
G$19,506 GYD per night
4.87 out of 5 average rating, 270 reviews
Guest favorite
Cottage in Cambridge
Church Creek - waterfront cottage & pool - private
Dec 19 – 26
G$38,607 GYD per night
4.99 out of 5 average rating, 106 reviews
Guest favorite
Guest suite in Piney Point
Spectacular beachfront walk-out in Piney Point MD
Jun 10 – 17
G$75,205 GYD per night
4.94 out of 5 average rating, 221 reviews
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
May 22 – 29
G$33,998 GYD per night
4.96 out of 5 average rating, 558 reviews
Guest favorite
Guest suite in Cambridge
Oakley Suite
Apr 27 – May 4
G$22,679 GYD per night
4.95 out of 5 average rating, 264 reviews
Guest favorite
Cottage in Edgewater
Waterfront Chesapeake Bay Getaway Firepit & Pier!
Nov 19 – 26
G$58,670 GYD per night
4.99 out of 5 average rating, 118 reviews

Home rentals in Maryland

Guest favorite
Home in Myersville
The Crooked Cottage: a Cozy, Curated Escape
Jun 22 – 29
G$30,448 GYD per night
4.96 out of 5 average rating, 141 reviews
Guest favorite
Home in Silver Spring
Entire Guest Suite/Apt in Silver Spring
Aug 9 – 16
G$18,239 GYD per night
4.99 out of 5 average rating, 144 reviews
Guest favorite
Home in Silver Spring
Cozy One Bedroom Apartment Near DC
Jun 2 – 9
G$14,968 GYD per night
4.94 out of 5 average rating, 175 reviews
Guest favorite
Home in Lusby
Historic Rousby Hall, Waterfront, Patuxent River
Mar 21 – 28
G$109,493 GYD per night
5.0 out of 5 average rating, 110 reviews
Guest favorite
Home in Swanton
Bev's House at Sunny Meadows
Jun 1 – 8
G$31,048 GYD per night
4.98 out of 5 average rating, 184 reviews
Guest favorite
Home in North East
Private home
Jan 25 – Feb 1
G$17,156 GYD per night
4.9 out of 5 average rating, 122 reviews
Guest favorite
Home in Silver Spring
Quiet, Modern Apartment - Metro Accessible.
Dec 23 – 30
G$12,284 GYD per night
4.83 out of 5 average rating, 160 reviews
Guest favorite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
Apr 8 – 15
G$188,988 GYD per night
5.0 out of 5 average rating, 103 reviews
Guest favorite
Home in Grasonville
River Front, Private Single Family Home
Oct 4 – 11
G$94,764 GYD per night
4.94 out of 5 average rating, 220 reviews
Guest favorite
Home in Parsonsburg
Forest Grove Retreat
Oct 2 – 9
G$21,059 GYD per night
4.83 out of 5 average rating, 115 reviews
Guest favorite
Home in Tracys Landing
The Little Gypsy BoHome
Oct 14 – 21
G$125,992 GYD per night
4.99 out of 5 average rating, 162 reviews
Guest favorite
Home in Lexington Park
Private beach retreat in historic St. Mary's City
Nov 20 – 27
G$83,725 GYD per night
4.97 out of 5 average rating, 136 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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