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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
Beachfront
Monthly stays
Gym

Maryland beach vacation rentals

Top guest favorite
The two-story condo is nestled along the canal, featuring multiple balconies with seating. A blue hammock is visible on the upper deck. Neighboring buildings and docked boats can be seen along the water's edge, surrounded by greenery and a clear sky.
Condo in Ocean City
5 out of 5 average rating, 31 reviews

Mid OC Bayside Canal Condo Remodeled-Pets Welcome!

Guest favorite
A spacious deck overlooks the calm bay, featuring a light-colored lounge chair positioned for relaxation. The water reflects the clear blue sky, enhancing the view. Nearby buildings add to the coastal charm, while the deck's railing provides a safe space for enjoyment.
Home in Ocean City
5 out of 5 average rating, 6 reviews

Seas The Bay on the Waterfront!

Top guest favorite
An open living area features plush seating arrangements in soft tones, complemented by a coffee table and an elegant fireplace beneath a mounted TV. Natural light filters through sheer curtains, enhancing the warm atmosphere of the space.
Cottage in Annapolis
5 out of 5 average rating, 11 reviews

Wonderful Cottage Nestled On Chesapeake Bay

Top guest favorite
A serene water view is captured at dusk, with a wooden dock extending over calm waters. Bare trees and lush greenery frame the scene, where a red hammock is visible beside the cottage, nestled among the trees, providing a peaceful spot to relax.
Home in Pasadena
5 out of 5 average rating, 29 reviews

Kayak Cove

Top guest favorite
A spacious living area is furnished with a comfortable sectional sofa and accent chairs, arranged around a wooden coffee table. Light wood accents and a large area rug complement the neutral tones of the room. Art pieces hang on the walls, adding visual interest.
Condo in Ocean City
5 out of 5 average rating, 103 reviews

Steps to Ocean! Uncrowded Beach. Midtown Retreat

Guest favorite
A charming cottage exterior is visible, featuring wooden shingles and a black metal roof. The pathway leads to the entrance, surrounded by a grassy lawn and neatly trimmed shrubs. Water views can be glimpsed in the distance, offering a serene outdoor setting.
Cottage in Charlestown
4.95 out of 5 average rating, 184 reviews

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

Top guest favorite
A two-story townhome is featured, characterized by its white exterior and green shutters. The well-maintained landscaping includes shrubs and small trees, enhancing the inviting appearance. A covered porch with steps leads to the entrance, located in a neighborhood with similar homes.
Home in Ocean City
5 out of 5 average rating, 31 reviews

Bay Dreamin; Townhouse steps to Beach & Boardwalk!

Top guest favorite
An inviting balcony showcases two blue adirondack chairs positioned for ocean views. A storage bench sits beneath the rail, while greenery hangs above, creating a serene outdoor space that overlooks sandy dunes and the ocean beyond.
Condo in Ocean City
4.96 out of 5 average rating, 80 reviews

Gorgeous New Beachfront! King Bed, Direct Sea View

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Home rentals in Maryland

Top guest favorite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron
5 out of 5 average rating, 112 reviews

Peace Point - Waterfront, Secluded, Home w/hot tub

Guest favorite
A spacious living area features large glass windows that frame a panoramic view of the Chesapeake Bay. Natural light illuminates the room, highlighting the wooden ceiling and modern decor. A seating arrangement overlooks an inviting outdoor patio with garden furniture, creating a seamless connection to the outdoors.
Home in Lusby
4.96 out of 5 average rating, 145 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Guest favorite
A large, welcoming two-story home is surrounded by well-maintained hedges and green lawns. The front porch features black shutters and multiple windows, contributing to the home's charm. Lush trees provide shade and natural beauty to the inviting outdoor space.
Home in Adamstown
4.96 out of 5 average rating, 107 reviews

Wizard's Escape | Sleep15+ | Pool | 2 EscapeRooms

Top guest favorite
The modern two-story cottage is set against a backdrop of lush greenery, featuring a well-manicured lawn and vibrant flower beds. Elevated views of the waterfront are visible in the distance, while a stone pathway leads to the front entrance adorned with wooden double doors.
Home in Shady Side
5 out of 5 average rating, 172 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

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, 172 reviews

Sunset Breezes - quiet waterfront retreat

Superhost
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, 136 reviews

Spacious Gorgeous Waterfront Home with Sunset View

Guest favorite
An expansive open-concept living area is highlighted by large windows, providing ample natural light and panoramic views of the surroundings. Comfortable seating areas are arranged around a central coffee table, while a cozy stone fireplace serves as a focal point against a feature wall.
Home in Smithsburg
4.95 out of 5 average rating, 149 reviews

The Great Escape Lodge ~ Exquisite Mountain Views

Top guest favorite
A single-story house is shown with blue siding and white trim, featuring a prominent brick chimney and a welcoming pink door. Large windows provide ample natural light. A grassy area surrounds the home, with trees adding greenery in the background.
Home in Piney Point
5 out of 5 average rating, 112 reviews

Living on Island Time

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Maryland fishing vacation rentals

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, 349 reviews

Riverfront Chalet Kayak/Canoe, pier, breakfast!

Guest favorite
The exterior of the cabin is presented, featuring a welcoming wooden façade with multiple large windows. A stone patio leads to the entrance, surrounded by green grass and colorful flowers. The area is shaded by surrounding trees, offering a peaceful and natural setting.
Cabin in North East
4.97 out of 5 average rating, 175 reviews

Waterfront Cabin on the Chesapeake

Top 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
4.97 out of 5 average rating, 188 reviews

Annapolis Area Waterside Retreat

Guest favorite
Cottage in Deale
4.82 out of 5 average rating, 182 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Top guest favorite
A view from the yard showcases blue outdoor chairs positioned on lush grass, with a pathway leading toward the water. The scene includes trees on either side, and glimpses of the waterfront and dock are visible in the distance.
Cottage in Smith Island
4.97 out of 5 average rating, 230 reviews

Levering Creek Cottage with Private Dock

Top guest favorite
A bright blue kayak rests on a wooden dock, with paddles and personal gear arranged beside it. Lush green vegetation lines the serene waterway, reflecting the surrounding nature and creating a peaceful atmosphere for outdoor enthusiasts.
Loft in Hebron
5 out of 5 average rating, 105 reviews

Waterfront Barn Loft with Modern Cabin Vibe

Top guest favorite
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 356 reviews

Historic St.Mary's City at the Lazy Bear Cottage

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
4.96 out of 5 average rating, 190 reviews

Cozy Lakeside Studio Retreat.

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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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