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Vacation rentals in Maryland

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Vacation rentals for every style

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Popular amenities for Maryland vacation rentals

Self check-in
Waterfront
Monthly stays
Pool
Gym

Maryland waterfront vacation rentals

Top guest favorite
A serene waterfront view reveals calm water framed by lush green trees. A small private dock is visible, featuring an orange kayak resting at the edge. The scene conveys tranquility, inviting relaxation amidst nature.
Guest suite in Chestertown
4.99 out of 5 average rating, 233 reviews

Beautiful Waterfront Chestertown Getaway

Top guest favorite
A charming cottage is visible beside a clear pool, surrounded by well-maintained green lawns. Two shaded umbrellas stand over cushioned lounge chairs by the water's edge, creating a comfortable outdoor space for relaxation. The inviting pool reflects the bright sky, enhancing the serene atmosphere.
Cottage in Easton
5 out of 5 average rating, 114 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Guest favorite
A spacious living area features a dark couch adorned with pillows, complemented by a light-colored chaise lounge. Large windows with striped curtains frame panoramic water views. A decorative area rug and a wooden coffee table enhance the room's inviting atmosphere.
Loft in Solomons
4.95 out of 5 average rating, 177 reviews

Stunning Waterfront Chef's Loft

Top guest favorite
A rustic barn loft is nestled among trees, featuring a welcoming staircase leading to the upper deck. Soft lights illuminate the entrance, enhancing the natural surroundings. The gravel driveway and landscaped area provide convenient access to the property, highlighting its serene setting.
Loft in Hebron
5 out of 5 average rating, 107 reviews

Waterfront Barn Loft with Modern Cabin Vibe

Top guest favorite
The exterior of the cottage is framed by vibrant flowerbeds filled with blooming roses and lush green shrubs. A well-manicured path leads to the entrance, flanked by tall greenery, with glimpses of the sparkling water visible in the background.
Home in Shady Side
5 out of 5 average rating, 182 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Guest favorite
The exterior of the farmhouse showcases a large, white structure with multiple windows and a spacious lawn surrounded by trees. The scene is complemented by a clear sky, creating a serene environment. Outdoor seating appears to be arranged on the patio, inviting relaxation.
Home in Chester
4.94 out of 5 average rating, 104 reviews

Waterfront Farmhouse Meets Modern Luxury

Top guest favorite
A wooden dock extends into calm waters, leading towards a bright waterfront home with light-colored siding. Surrounding trees provide a natural backdrop, while a sandy beach is visible to the right. Soft evening light casts a warm glow over the scene.
Cottage in Leonardtown
4.96 out of 5 average rating, 109 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Top guest favorite
The living area features large sliding doors that open to a porch with stunning bay views during sunset. A neutral-colored couch and a cozy chair create a welcoming space. A wooden dining table complements the serene atmosphere, illuminated by the warm glow from the setting sun.
Townhouse in Ocean City
4.97 out of 5 average rating, 468 reviews

Edgewater Escape - Luxury Bayfront Loft with Porch

Home rentals in Maryland

Top guest favorite
A spacious mountain home is set against a backdrop of trees, with a gently sloping field leading to a small pond in the foreground. A wooden fence encircles the property, highlighting the serene outdoor environment that encompasses the house.
Home in Sabillasville
4.94 out of 5 average rating, 130 reviews

Stoney Spring Overlook

Guest favorite
A comfortable living area features a light grey sofa adorned with soft blankets, positioned near a wooden coffee table. Two nautical-themed art pieces hang on the white shiplap wall, while a lamp casts a warm glow beside a potted plant. Steps lead to an upper level.
Home in Timonium
4.89 out of 5 average rating, 263 reviews

* Beautiful Oasis w/ No Detail Spared

Guest favorite
A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.
Home in Preston
4.92 out of 5 average rating, 106 reviews

River House on the Choptank

Guest favorite
Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.
Home in Edgewater
4.96 out of 5 average rating, 196 reviews

Annapolis Area Waterside Retreat

Top guest favorite
A single-story home is set amidst a lush, green lawn, surrounded by trees and natural vegetation. The exterior features a light-colored facade with a welcoming front entry and flower beds to the sides, enhancing the serene atmosphere of the wooded location.
Home in Greensboro
4.97 out of 5 average rating, 104 reviews

Cozy 2 bedroom home on wooded private lane

Top guest favorite
A spacious house is set against a winter backdrop, surrounded by snow-covered trees. The porch, featuring seating, can be seen along with a stone pathway leading to the entrance. Snowflakes gently fall, creating a serene and quiet atmosphere.
Home in Greensboro
4.98 out of 5 average rating, 162 reviews

Cozy Riverside Cottage in the Woods

Top guest favorite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge
4.99 out of 5 average rating, 178 reviews

Sunset Breezes - quiet waterfront retreat

Guest favorite
The living room features a high, wooden ceiling with large windows allowing natural light to fill the space. A comfortable arrangement of sofas and chairs offers ample seating, complemented by a stylish area rug. A modern fireplace adds warmth to the inviting design.
Home in Perry Hall
4.99 out of 5 average rating, 111 reviews

Gunpowder Retreat

Maryland fishing vacation rentals

Guest favorite
Cabin in McHenry
4.97 out of 5 average rating, 138 reviews

Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTDOOR MOVIE EXPERIENCE*HOT TUB*1.8mi to WISP*WORK SPACES*wood CRIB!

Guest favorite
A bright living area features large windows offering views of the Chesapeake Bay. A modern chandelier hangs from the wooden ceiling above a cozy seating arrangement, while a sleek television is mounted on the wall. A deck is visible outside, inviting outdoor relaxation.
Home in Lusby
4.96 out of 5 average rating, 149 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Top guest favorite
Two light blue Adirondack chairs are positioned on a wooden dock, facing a calm river. The sun sets over the water, casting a warm glow across the surface and creating a serene atmosphere. A weathered wooden table is placed nearby, enhancing the inviting scene.
Guest suite in Lusby
4.98 out of 5 average rating, 355 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Guest favorite
An aerial view captures a serene landscape featuring a red barn, a charming house, and a pond. Lush green fields and trees surround the property, creating a tranquil retreat. A winding path leads through the area, emphasizing the open space and natural beauty of the surroundings.
Guesthouse in Westminster
4.88 out of 5 average rating, 344 reviews

The Pig Shed Writer’s Retreat at Barter Lady Farm

Top guest favorite
An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.
Home in Cobb Island
4.99 out of 5 average rating, 107 reviews

Waterfront 4-BR home w/ hot tub & charging station

Top guest favorite
A tranquil waterfront setting features a multi-level home surrounded by trees, with a spacious deck visible. Adirondack chairs on the dock face the calm waters, reflecting the structure and greenery. Soft outdoor lighting adds a cozy ambiance, enhancing the serene landscape.
Guesthouse in Lusby
4.97 out of 5 average rating, 201 reviews

Cozy Lakeside Studio Retreat.

Guest favorite
Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.
Home in Scotland
4.9 out of 5 average rating, 140 reviews

Spacious Gorgeous Waterfront Home with Sunset View

Guest favorite
A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.
Cabin in Worton
4.94 out of 5 average rating, 101 reviews

Cabin on the Creek ~ Kayaks and Fire Pit

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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