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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.

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Guest favorite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

ValueLocationAccuracy

4.92 out of 5 average rating, 267 reviews
Top guest favorite
The log cabin features a warm wooden exterior with a blue metal roof, nestled among trees. A screened porch allows for outdoor enjoyment while a fire pit is positioned nearby, surrounded by natural stone. The peaceful setting invites relaxation amidst the greenery.
Cabin in Myersville

Sleepy Hollow Log Cabin

Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

ValueLocationGrill

4.96 out of 5 average rating, 216 reviews
Top guest favorite
The treehouse is elevated among bare branches, featuring a large deck with seating. Warm lighting highlights the wooden exterior, and expansive windows provide views of the surrounding forest. Steps lead down to the ground, enhancing accessibility to the natural setting.
Treehouse in McHenry

Bird's Eye View

Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

LocationValueOutdoor spaces

4.99 out of 5 average rating, 218 reviews
Top guest favorite
A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.
Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

ValueLocationAccess

4.99 out of 5 average rating, 149 reviews
Top guest favorite
Home in Cobb Island

*Solitude At Sunset*

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

FamilyLocationTV

4.97 out of 5 average rating, 102 reviews
Guest favorite
Treehouse in McHenry

Treehouse in Deep Creek Lake

Newly built, Whispering Woods is a custom-made treehouse surrounded by stunning scenery just minutes from Deep Creek Lake and Wisp Resort. No detail was overlooked in the spacious interior that includes 2 bedrooms, 2 baths, a fully equipped kitchen, and a sitting area with a 65” TV. The amazing outdoor living space includes expansive decks, a fire pit, and a bubbling hot tub. For a unique and memorable experience from start to finish, come relax and reconnect at this treetop escape.

LocationValueHot tub

4.95 out of 5 average rating, 150 reviews
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

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

ValueLocationNearby

4.99 out of 5 average rating, 224 reviews
Top guest favorite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

LocationFamilyWalkability

5.0 out of 5 average rating, 214 reviews
Top guest favorite
Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

FamilyLocationKitchen

4.96 out of 5 average rating, 296 reviews
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

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

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

ValueFamilyWifi

4.99 out of 5 average rating, 142 reviews
Top guest favorite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

ValueFamilyCheck-in

4.99 out of 5 average rating, 364 reviews
Top guest favorite
A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.
Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

FamilyLocationCheck-in

4.97 out of 5 average rating, 110 reviews

Popular amenities for Maryland vacation rentals

Self check-inWaterfrontMonthly staysPoolGym

Maryland waterfront vacation rentals

Top guest favorite
The charming exterior of a waterfront cottage, featuring a white picket fence and a welcoming front deck. Large windows allow for natural light, while vibrant surroundings enhance the coastal feel. The front porch is partially shaded by lush greenery, inviting relaxation and enjoyment of the outdoors.
Cottage in North Beach

Cozy Waterfront Cottage - Pet Friendly

LocationFamilyPets

4.95 out of 5 average rating, 107 reviews
Guest favorite
A spacious bed is adorned with decorative orange pillows and flanked by elegant bedside lamps. Framed artwork featuring floral designs hangs above the headboard, complementing the soft color palette of the room.
Home in Fells Point

Luxury Fells Home w/Hot Tub, Poker Room, & Parking

FamilyLocationAir conditioning

4.96 out of 5 average rating, 116 reviews
Top guest favorite
A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.
Home in Mechanicsville

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

FamilyValueHiking

5.0 out of 5 average rating, 105 reviews
Top guest favorite
Cottage in Leonardtown

Beach Front and 'Perfectly Placed'

FamilyValueLaundry

4.96 out of 5 average rating, 275 reviews
Top guest favorite
An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.
Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

FamilyLocationDecor

4.99 out of 5 average rating, 264 reviews
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

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

ValueFamilyTV

4.99 out of 5 average rating, 140 reviews
Top guest favorite
The exterior of the guesthouse is showcased, featuring a deck with outdoor seating and an umbrella. Tall windows allow for natural light, complementing the green siding. Lush landscaping surrounds the house, creating a natural, inviting setting.
Guesthouse in Smithsburg

Jewel Vinsota Artist's Guesthouse

FamilyValueCleanliness

4.97 out of 5 average rating, 859 reviews
Guest favorite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale

Chesapeake Bay Cottage

LocationValueCheckout

4.96 out of 5 average rating, 182 reviews

Vacation rentals with pools in Maryland

Superhost
A large, two-story home with a welcoming front porch is set amidst a spacious green lawn. The house features a grey exterior with white trim and multiple windows, surrounded by trees and landscaping, creating a peaceful and private atmosphere.
Home in Severn

Large Home w/ Private Pool, Gym, Sauna, 7 Bedrooms

LocationFamilyIndoor spaces

4.86 out of 5 average rating, 222 reviews
Top guest favorite
Farm stay in Huntingtown

Luxury Farmette -Private & Secluded-1hr to DC

LocationValueIndoor spaces

5.0 out of 5 average rating, 125 reviews
Top guest favorite
Apartment in Upper Marlboro

Kone Oasis- hot tub, pool, theater/game rm.

FamilyLocationLong stay

4.94 out of 5 average rating, 215 reviews
Top guest favorite
The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.
Home in Lusby

Historic Rousby Hall, Waterfront, Pool, Beach

FamilyLocationAccess

4.99 out of 5 average rating, 175 reviews
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

Gunpowder Retreat

LocationFamilyGrill

4.98 out of 5 average rating, 149 reviews
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

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

FamilyLocationGrill

5.0 out of 5 average rating, 125 reviews
Top guest favorite
A spacious bedroom is showcased with a king bed dressed in neutral linens and accented by two blue decorative pillows. Natural light filters through the two windows beside the bed, and a coastal-themed artwork adorns the wall above. Two bedside lamps provide additional soft lighting.
Guest suite in Arnold

Coastal Comfort Retreat near Annapolis, EV charger

FamilyValueComfort

4.94 out of 5 average rating, 226 reviews
Guest favorite
Home in Fort Washington

Inground Pool | Hot Tub | Sauna | Theme Room

LocationValueLaundry

4.89 out of 5 average rating, 229 reviews

Maryland home rentals

Superhost
Home in Bowie

Modern 6BR • Close to DC & Annapolis

ValueFamilyGrill

4.82 out of 5 average rating, 177 reviews
Top guest favorite
The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.
Home in Myersville

The Crooked Cottage: a Cozy, Curated Escape

LocationValueOutdoor spaces

4.98 out of 5 average rating, 316 reviews
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

Spacious Gorgeous Waterfront Home with Sunset View

FamilyLocationAccuracy

4.89 out of 5 average rating, 168 reviews
Top guest favorite
The log cabin features a spacious covered porch surrounded by trees. The wooden structure blends into the natural setting, while large windows invite natural light. The front yard is landscaped with shrubs, providing a warm and inviting entrance.
Home in Thurmont

Cabin in the Woods - Weekday Specials!

ValueFamilyCheck-in

4.87 out of 5 average rating, 635 reviews
Top guest favorite
A bright and open living space features large windows that provide views of the river. A long dining table is accompanied by upholstered chairs. A modern kitchen counter with stools is visible, along with a chandelier overhead and a cozy fireplace on one side.
Home in St. Leonard

Blue Pearl-Luxury estate with private dock/jacuzzi

LocationFamilyKitchen

4.97 out of 5 average rating, 105 reviews
Top guest favorite
A cozy living area features a gray sectional sofa with a yellow throw draped over it. Wood accents and a patterned area rug complement the warm hardwood floors. An adjacent dining space is visible, showcasing a rustic brick wall and a dining table with elegant lighting.
Home in Fells Point

Charming 4 bedroom home just steps to the water!

LocationFamilyParking

4.95 out of 5 average rating, 197 reviews
Top guest favorite
Home in Deale

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

ValueFamilyAccuracy

4.98 out of 5 average rating, 151 reviews
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

Annapolis Area Waterside Retreat

ValueFamilyDecor

4.95 out of 5 average rating, 262 reviews

All about 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.

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.

Destinations to explore