Maryland vacation rentals
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Top-rated vacation rentals in Maryland
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Cabin in Myersville
4.97 out of 5 average rating, 247 reviewsCabin 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.
Mar 19 – 26
Guest suite in Lusby
4.99 out of 5 average rating, 299 reviewsRiverfront Chalet Kayak/Canoe, pier, breakfast!
This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own completely private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is beautiful Solomon’s island. Boaters welcome!
Feb 25 – Mar 4
Tiny home in Saint Inigoes
4.98 out of 5 average rating, 292 reviewsHistoric 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 13 – 20
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Maryland vacation rentals
Maryland waterfront vacation rentals
Guesthouse in Glen Burnie
4.94 out of 5 average rating, 259 reviewsThe Crab House - a Private, Waterfront Guest House
Feb 22 – Mar 1
Apartment in Pasadena
4.99 out of 5 average rating, 541 reviewsSea Dreamer aka Phenomenal Hospitality
Nov 16 – 23
Cottage in Leonardtown
4.97 out of 5 average rating, 119 reviewsBeach Front and 'Perfectly Placed'
Jan 10 – 17
Guesthouse in White Marsh
4.97 out of 5 average rating, 137 reviewsBird River Bottega - A Waterfront Oasis!
Feb 19 – 26
Guesthouse in Bushwood
4.92 out of 5 average rating, 142 reviewsLittle House by the water
Jan 7 – 14
Guesthouse in Annapolis
4.99 out of 5 average rating, 102 reviewsCoastal Waterfront 1 Bedroom Cottage
Apr 29 – May 6
Home in Shady Side
5.0 out of 5 average rating, 113 reviewsLuxe Modern Chesapeake Waterfront Oasis - 5 Star
Mar 18 – 25
Home in Cambridge
5.0 out of 5 average rating, 263 reviews"Happy Campers" Waterfront Apartment!
Mar 8 – 15
Cottage in Saint Leonard
4.99 out of 5 average rating, 101 reviewsCaptain Jack's Bay Hideaway
Sep 3 – 10
Cottage in Saint Michaels
4.99 out of 5 average rating, 135 reviewsLa Casita on Harris Creek, St. Michaels
Jul 15 – 22
Guesthouse in Stevensville
5.0 out of 5 average rating, 202 reviewsWaterfront Getaway - View of bay from your bed
Nov 8 – 15
Apartment in Leonardtown
4.98 out of 5 average rating, 119 reviewsStunning Sunsets on Breton Bay, Seaside apartment
Jul 2 – 9
Maryland fishing vacation rentals
Bungalow in Deale
4.86 out of 5 average rating, 353 reviewsCozy waterfront getaway on the Bay
Jan 24 – 31
Tiny home in Cambridge
4.89 out of 5 average rating, 492 reviewsBlackwater Tiny Cabin on Snakehead Creek
Nov 29 – Dec 6
Cabin in Lusby
4.93 out of 5 average rating, 138 reviewsHideaway on the Bay: Waterfront Vintage A Frame
Jul 14 – 21
Cottage in Edgewater
4.99 out of 5 average rating, 122 reviewsWaterfront Chesapeake Bay Getaway Firepit & Pier!
Nov 11 – 18
Guesthouse in Riva
4.99 out of 5 average rating, 273 reviewsThe Riva House
Mar 2 – 9
Cottage in Westover
4.99 out of 5 average rating, 178 reviewsRumbley Cottage on the Tangier Sound-Private Beach
Nov 25 – Dec 2
Home in Cambridge
4.92 out of 5 average rating, 176 reviewsGuest House: Farm homestead
Jul 3 – 10
Guesthouse in Westminster
4.86 out of 5 average rating, 271 reviewsThe Pig Shed Writer’s Retreat at Barter Lady Farm
Apr 9 – 16
Townhouse in Port Deposit
4.96 out of 5 average rating, 144 reviewsQuarry Landing *River View* in Port Deposit
Cottage in Cambridge
4.99 out of 5 average rating, 107 reviewsChurch Creek - waterfront cottage & pool - private
Feb 28 – Mar 7
Guest suite in Piney Point
4.94 out of 5 average rating, 222 reviewsSpectacular beachfront walk-out in Piney Point MD
Jul 27 – Aug 3
Guest suite in Arnold
4.96 out of 5 average rating, 560 reviewsOld Bay Bungalow
May 22 – 29
Home rentals in Maryland
Home in Myersville
4.97 out of 5 average rating, 143 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Jul 26 – Aug 2
Home in Silver Spring
4.99 out of 5 average rating, 145 reviewsEntire Guest Suite/Apt in Silver Spring
Mar 5 – 12
Home in Rock Hall
5.0 out of 5 average rating, 102 reviewsBayside Beach House
Jun 1 – 8
Home in Tracys Landing
4.99 out of 5 average rating, 162 reviewsThe Little Gypsy BoHome
Oct 12 – 19
Home in Glenn Dale
4.78 out of 5 average rating, 199 reviewsClean & Cozy Private Basement Apt - 15mins from DC
Sep 6 – 13
Home in Swanton
4.98 out of 5 average rating, 185 reviewsBev's House at Sunny Meadows
Sep 12 – 19
Home in Silver Spring
4.94 out of 5 average rating, 176 reviewsCozy One Bedroom Apartment Near DC
Jun 9 – 16
Home in Grasonville
4.94 out of 5 average rating, 221 reviewsRiver Front, Private Single Family Home
Dec 22 – 29
Home in Lusby
4.98 out of 5 average rating, 259 reviewsCove Point Beach Cabin
Dec 22 – 29
Home in Kent Narrows
5.0 out of 5 average rating, 275 reviewsChester Riverfront At Kent Narrows
Nov 6 – 13
Home in Baltimore
4.91 out of 5 average rating, 124 reviewsSouth Baltimore's Best!
Nov 15 – 22
Home in Hyattsville
4.93 out of 5 average rating, 206 reviewsSunny, private apartment in historic neighborhood
Oct 21 – 28
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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