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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 --

ValueFamilyTV

4.91 out of 5 average rating, 270 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.

LocationValueGrill

4.99 out of 5 average rating, 222 reviews
Top guest favorite
Cabin in Grantsville

Lovers Escape! Riverside Sauna! Riverview Hot Tub

Kick back and relax by the beautiful Casselman River. (30 minutes from Deep Creek Lake) Nestled in the Pines, River views from your hot tub, soaking tub in the bathroom with robes for you and your partner (two bath bombs and shower steamers included), king size bed, high end Breville Espresso Machine, and more! The cabin is nearby plenty of state parks, restaurants, coffee shops, and has so much to offer for couples looking to escape the busyness of life for a few days. Hope to see you soon!

LocationFamilyDecor

4.96 out of 5 average rating, 113 reviews
Guest favorite
An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.
Home in Riviera Beach

Waterfront Cheerful 5 home

Welcome to this brand-new relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

FamilyLocationCleanliness

4.94 out of 5 average rating, 181 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.

ValueLocationView

4.99 out of 5 average rating, 152 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

Treat yourself to a luxury getaway with a 6-person hot tub, poker room with record player, and a gorgeously renovated bathroom with a freestanding soaking tub. This opulently decorated, spacious, renovated townhouse is located in the heart of very safe Fells Point. Sleeping arrangements for 6. Blazing fast 1GB Wifi, dedicated work space, 1 street parking permit, 65" Smart TV, and only 3 short blocks (3 min walk) to the bustling Fells Point waterfront. Just far enough to sleep undisturbed!

ValueLocationHospitality

4.95 out of 5 average rating, 122 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.

FamilyLocationDecor

4.95 out of 5 average rating, 155 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...

ValueFamilyGrill

4.96 out of 5 average rating, 300 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.

ValueFamilyHeating

4.99 out of 5 average rating, 371 reviews
Top guest favorite
The cabin exterior showcases a blend of rustic wooden siding and modern architectural design. Warm lights illuminate large windows, highlighting the inviting entrance. Surrounding trees provide a natural backdrop, and a large stone is visible in the foreground, enhancing the private woodland setting.
Cabin in Accident

Rustic Luxe Cabin (4x4 Required)

Situated on 10 acres and surrounded by a 600-acre nature conservancy, Rustic Lux is a new construction that fuses the charming details of a rustic cabin with high-end modern luxury. Guests can enjoy complete privacy with quick access to all the wonders of Deep Creek Lake! Rustic Lux is only 4 miles from the lake and Wisp Ski Resort. The road back to the cabin is a little rough but is pretty flat and in no way dangerous. We recommend 4 wheel drive vehicles.

FamilyLocationGrill

4.98 out of 5 average rating, 100 reviews
Top guest favorite
Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

FamilyValueOutdoor spaces

5.0 out of 5 average rating, 226 reviews
Superhost
Home in Bowie

Modern 6BR • Close to DC & Annapolis

Bright and spacious 6 bedroom, 5.5 bathroom home with a gym and sauna in a quiet, safe Largo neighborhood. Perfect for families and relaxed groups. Woodmore Town Center is under 5 minutes for groceries, dining, and shopping. About 20 minutes to DC and Silver Spring, with the Largo Town Metro only 7 minutes away for easy access to all major lines. Fast Wi-Fi, comfy beds, friendly neighbors, and plenty of space to unwind.

ValueFamilyAccess

4.82 out of 5 average rating, 179 reviews

Popular amenities for Maryland vacation rentals

Self check-inWaterfrontMonthly staysPoolGym

Maryland waterfront vacation rentals

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

LocationFamilyComfort

4.99 out of 5 average rating, 142 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

LocationValueGetting around

4.99 out of 5 average rating, 228 reviews
Top guest favorite
A wooden deck is presented with two rocking chairs, positioned on a textured area rug. Surrounding trees offer a lush backdrop, enhancing the natural setting. The rustic log construction of the cabin complements the peaceful ambiance of the outdoor space.
Cabin in Cecil County

Waterfront cabin home - 9+ private wooded acres

LocationFamilyIndoor spaces

5.0 out of 5 average rating, 132 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

ValueFamilyBiking

4.99 out of 5 average rating, 266 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.

FamilyValueOutdoor spaces

5.0 out of 5 average rating, 107 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

LocationValueHiking

4.95 out of 5 average rating, 185 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

FamilyLocationLayout

4.99 out of 5 average rating, 179 reviews
Top guest favorite
A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.
Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

FamilyValueAir conditioning

4.97 out of 5 average rating, 473 reviews

Vacation rentals with pools in Maryland

Top guest favorite
Farm stay in Huntingtown

Luxury Farmette -Private & Secluded-1hr to DC

FamilyLocationOutdoor spaces

4.99 out of 5 average rating, 129 reviews
Guest favorite
Apartment in Upper Marlboro

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

ValueLocationQuiet

4.94 out of 5 average rating, 218 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

FamilyLocationBackyard

5.0 out of 5 average rating, 126 reviews
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

Stoney Spring Overlook

ValueFamilyKitchen

4.95 out of 5 average rating, 156 reviews
Guest favorite
Guest suite in Arnold

Pet-Friendly King Suite + Kitchen | Near Annapolis

FamilyValueQuiet

4.95 out of 5 average rating, 217 reviews
Top guest favorite
The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.
Home in Stevensville

Beautiful Kent Island Getaway with Pool

ValueLocationGetting around

4.97 out of 5 average rating, 133 reviews
Guest favorite
An aerial view of a spacious red farmhouse surrounded by lush greenery and open fields. A saltwater pool is visible in the backyard, complemented by a patio area. The landscape includes manicured lawns and trees, creating a serene rural setting.
Home in Queen Anne

Farmhouse w/hot tub, close to Tuckohoe State Park

LocationFamilyIndoor spaces

4.96 out of 5 average rating, 113 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

FamilyLocationCleanliness

4.98 out of 5 average rating, 152 reviews

Maryland home rentals

Top guest favorite
Home in Sharpsburg

Steps to Winery and Battlefield – 1 Acre Retreat

LocationFamilyPets

4.96 out of 5 average rating, 248 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.

LocationFamilyHeating

4.97 out of 5 average rating, 113 reviews
Guest favorite
A large flat-screen television is mounted on a brick wall above a stone fireplace. The screen displays a colorful scene of hot air balloons against a blue sky. Surrounding the fireplace are potted plants and shelves filled with DVDs, adding to the cozy atmosphere.
Home in Glen Burnie

Glen Burnie Escape

LocationValueAir conditioning

4.98 out of 5 average rating, 129 reviews
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

River House on the Choptank

FamilyLocationComfort

4.92 out of 5 average rating, 129 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

ValueLocationOutdoor spaces

4.99 out of 5 average rating, 142 reviews
Top guest favorite
Home in Deale

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

ValueFamilyNearby

4.98 out of 5 average rating, 155 reviews
Top guest favorite
The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.
Home in Solomons

The Little House on Back Creek

FamilyValueCheck-in

5.0 out of 5 average rating, 143 reviews
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!

FamilyValueBathroom

4.87 out of 5 average rating, 639 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