Maryland vacation rentals

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Top-rated vacation rentals in Maryland

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Cabin in Myersville

4.97 out of 5 average rating, 247 reviews

Cabin 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

G$23,743 GYD per night
Guest favorite

Guest suite in Lusby

4.99 out of 5 average rating, 299 reviews

Riverfront 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

G$27,155 GYD per night
Guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 292 reviews

Historic 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

G$17,272 GYD per night

Popular amenities for Maryland vacation rentals

Maryland waterfront vacation rentals

Guest favorite

Guesthouse in Glen Burnie

4.94 out of 5 average rating, 259 reviews

The Crab House - a Private, Waterfront Guest House

Feb 22 – Mar 1

G$49,625 GYD per night
Guest favorite

Apartment in Pasadena

4.99 out of 5 average rating, 541 reviews

Sea Dreamer aka Phenomenal Hospitality

Nov 16 – 23

G$19,755 GYD per night
Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 119 reviews

Beach Front and 'Perfectly Placed'

Jan 10 – 17

G$33,076 GYD per night
Guest favorite

Guesthouse in White Marsh

4.97 out of 5 average rating, 137 reviews

Bird River Bottega - A Waterfront Oasis!

Feb 19 – 26

G$19,144 GYD per night
Guest favorite

Guesthouse in Bushwood

4.92 out of 5 average rating, 142 reviews

Little House by the water

Jan 7 – 14

G$18,902 GYD per night
Guest favorite

Guesthouse in Annapolis

4.99 out of 5 average rating, 102 reviews

Coastal Waterfront 1 Bedroom Cottage

Apr 29 – May 6

G$79,451 GYD per night
Guest favorite

Home in Shady Side

5.0 out of 5 average rating, 113 reviews

Luxe Modern Chesapeake Waterfront Oasis - 5 Star

Mar 18 – 25

G$100,777 GYD per night
Superhost

Home in Cambridge

5.0 out of 5 average rating, 263 reviews

"Happy Campers" Waterfront Apartment!

Mar 8 – 15

G$32,394 GYD per night
Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 101 reviews

Captain Jack's Bay Hideaway

Sep 3 – 10

G$32,272 GYD per night
Guest favorite

Cottage in Saint Michaels

4.99 out of 5 average rating, 135 reviews

La Casita on Harris Creek, St. Michaels

Jul 15 – 22

G$116,879 GYD per night
Guest favorite

Guesthouse in Stevensville

5.0 out of 5 average rating, 202 reviews

Waterfront Getaway - View of bay from your bed

Nov 8 – 15

G$59,183 GYD per night
Guest favorite

Apartment in Leonardtown

4.98 out of 5 average rating, 119 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

Jul 2 – 9

G$31,631 GYD per night

Maryland fishing vacation rentals

Superhost

Bungalow in Deale

4.86 out of 5 average rating, 353 reviews

Cozy waterfront getaway on the Bay

Jan 24 – 31

G$38,190 GYD per night
Superhost

Tiny home in Cambridge

4.89 out of 5 average rating, 492 reviews

Blackwater Tiny Cabin on Snakehead Creek

Nov 29 – Dec 6

G$17,622 GYD per night
Guest favorite

Cabin in Lusby

4.93 out of 5 average rating, 138 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

Jul 14 – 21

G$68,199 GYD per night
Guest favorite

Cottage in Edgewater

4.99 out of 5 average rating, 122 reviews

Waterfront Chesapeake Bay Getaway Firepit & Pier!

Nov 11 – 18

G$67,203 GYD per night
Guest favorite

Guesthouse in Riva

4.99 out of 5 average rating, 273 reviews

The Riva House

Mar 2 – 9

G$32,029 GYD per night
Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 178 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Nov 25 – Dec 2

G$70,510 GYD per night
Guest favorite

Home in Cambridge

4.92 out of 5 average rating, 176 reviews

Guest House: Farm homestead

Jul 3 – 10

G$26,103 GYD per night
Guest favorite

Guesthouse in Westminster

4.86 out of 5 average rating, 271 reviews

The Pig Shed Writer’s Retreat at Barter Lady Farm

Apr 9 – 16

G$21,480 GYD per night
Guest favorite

Townhouse in Port Deposit

4.96 out of 5 average rating, 144 reviews

Quarry Landing *River View* in Port Deposit

G$18,431 GYD per night
Guest favorite

Cottage in Cambridge

4.99 out of 5 average rating, 107 reviews

Church Creek - waterfront cottage & pool - private

Feb 28 – Mar 7

G$43,136 GYD per night
Guest favorite

Guest suite in Piney Point

4.94 out of 5 average rating, 222 reviews

Spectacular beachfront walk-out in Piney Point MD

Jul 27 – Aug 3

G$88,113 GYD per night
Guest favorite

Guest suite in Arnold

4.96 out of 5 average rating, 560 reviews

Old Bay Bungalow

May 22 – 29

G$38,698 GYD per night

Home rentals in Maryland

Guest favorite

Home in Myersville

4.97 out of 5 average rating, 143 reviews

The Crooked Cottage: a Cozy, Curated Escape

Jul 26 – Aug 2

G$35,080 GYD per night
Guest favorite

Home in Silver Spring

4.99 out of 5 average rating, 145 reviews

Entire Guest Suite/Apt in Silver Spring

Mar 5 – 12

G$21,077 GYD per night
Guest favorite

Home in Rock Hall

5.0 out of 5 average rating, 102 reviews

Bayside Beach House

Jun 1 – 8

G$32,759 GYD per night
Guest favorite

Home in Tracys Landing

4.99 out of 5 average rating, 162 reviews

The Little Gypsy BoHome

Oct 12 – 19

G$144,043 GYD per night
Guest favorite

Home in Glenn Dale

4.78 out of 5 average rating, 199 reviews

Clean & Cozy Private Basement Apt - 15mins from DC

Sep 6 – 13

G$21,723 GYD per night
Guest favorite

Home in Swanton

4.98 out of 5 average rating, 185 reviews

Bev's House at Sunny Meadows

Sep 12 – 19

G$35,657 GYD per night
Guest favorite

Home in Silver Spring

4.94 out of 5 average rating, 176 reviews

Cozy One Bedroom Apartment Near DC

Jun 9 – 16

G$17,973 GYD per night
Guest favorite

Home in Grasonville

4.94 out of 5 average rating, 221 reviews

River Front, Private Single Family Home

Dec 22 – 29

G$112,295 GYD per night
Guest favorite

Home in Lusby

4.98 out of 5 average rating, 259 reviews

Cove Point Beach Cabin

Dec 22 – 29

G$36,169 GYD per night
Guest favorite

Home in Kent Narrows

5.0 out of 5 average rating, 275 reviews

Chester Riverfront At Kent Narrows

Nov 6 – 13

G$79,617 GYD per night
Guest favorite

Home in Baltimore

4.91 out of 5 average rating, 124 reviews

South Baltimore's Best!

Nov 15 – 22

G$15,430 GYD per night
Guest favorite

Home in Hyattsville

4.93 out of 5 average rating, 206 reviews

Sunny, private apartment in historic neighborhood

Oct 21 – 28

G$26,366 GYD per night

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.

Destinations to explore

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