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Apartments in Maryland and Houses - Holiday Lettings - Holiday Rentals Maryland

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640 Holiday homes

Holiday home with swimming pool in Maryland

Marion Station house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

from £921 / night

£6,447 / week

1 / 30

Maryland holiday condo rental

Oxon Hill condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £153 / night

£1,069 / week

1 / 27

Condo rental in Ocean City with shared pool

Ocean City condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £144 / night

£1,157 / week

1 / 32

Holiday apartment in Fort Washington

Fort Washington apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £50 / night

£346 / week

1 / 39

Holiday condo rental

Ocean City condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £255 / night

£1,782 / week

1 / 14

Holiday home rental

St. Michaels house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £579 / night

£2,037 / week

1 / 4

Holiday condo with shared pool in Maryland

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from £384 / night

£2,685 / week

1 / 11

Condo rental in Maryland with shared pool

Ocean City condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £292 / night

£2,037 / week

1 / 16

Home letting in Maryland

Port Tobacco house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £249 / night

£1,655 - £3,210 / week

1 / 6

Holiday townhouse in Maryland

Clarksburg townhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 1

from £92 / night

£602 / week

1 / 4

Holiday cottage accommodation

Ocean City cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from £278 / night

£2,314 / week

1 / 23

Holiday private room rental

Silver Spring private room

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

from £172 / night

£1,199 / week

1 / 15

Holiday condo rental

National Harbor condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £425 / night

£2,974 / week

1 / 10

Holiday townhouse in Maryland

Silver Spring townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

from £241 / night

£1,685 / week

1 / 19

Maryland holiday home rental

Upper Marlboro house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £162 / night

£972 / week

1 / 6

Holiday condo in Ocean City

Ocean City condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Wonderful Stay” The place was wonderful, clean and Perry was quick to respond to any questions we had. It was a perfect place for our weekend girls trip to the beach. Would definitely stay there again!

from £135 / night

£866 - £1,296 / week

1 / 23

Holiday condo in Maryland

Ocean City condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £204 / night

£1,019 - £3,471 / week

1 / 44

Holiday condo rental

Ocean City condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £741 / night

£2,777 / week

1 / 20

Holiday home in St. Michaels

St. Michaels house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £695 / night

£4,165 / week

1 / 18

Home rental in Maryland

Elkton house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £24 / night

£148 / week

1 / 3

Holiday condo with shared pool in Maryland

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Perfect location. Perfect condo” Great location, for our annual golf tournament. Condo was perfect. Would definitely go back next year.

from £167 / night

£1,088 / week

1 / 14

Holiday home rental

Kent Island house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

“Love Point Retreat” I stayed at Paula's property 3 times so far. We stayed once in October 2014 and twice in April 2015. Here is how I would break it up: Owner: Paula is very nice, accommodating and extremely responsive. She was easy to deal with, answered all of our questions and concerns timely. Property (Interior): The property is really clean and very well maintained considering its age. I also feel that it is properly stocked with all the necessities. Property (Outdoor Space / View): We spend the majority of our time there outside. The deck / backyard area is very well maintained and stocked with adequate furniture. We used the gas grill every day of our stay. The dock is set up nicely for fishing including rod holders and a light for night fishing. The view from the dock is to die for, the Bay is so wide and the Bay Bridge is a nice backdrop to the view specially during sunset. Fishing: Fishing is the best I have ever experienced (compared to all other rentals I tried). I caught numerous species from the dock including Spot, White Perch and of course Striped Bass (Rockfish). I caught my biggest Rockfish ever from the dock there (39 inch fish, roughly 30 pounds) in April. Overall, I love the property, the view and the peaceful surroundings. A great bonus for me is the short one hour commute to get there. We will definitely be back to Love Point for an encore.

from £371 / night

£2,314 - £3,869 / week

1 / 20

Holiday apartment in Maryland

Pikesville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £139 / night

£602 - £1,250 / week

1 / 11

Condo rental in Ocean City with shared pool

Ocean City condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £213 / night

£1,435 / week

1 / 35

Maryland holiday condo rental

Ocean City condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £209 / night

£1,458 / week

1 / 7

Maryland holiday condo rental

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from £232 / night

£1,111 - £2,407 / week

1 / 22

Fairplay holiday b&b rental

Fairplay b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 2

from £139 / night

£972 / week

1 / 11

Maryland holiday condo rental

Ocean City condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £417 / night

£2,916 / week

1 / 71

Holiday hotel apartment with shared pool in Maryland

Ocean City hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £166 / night

£1,160 / week

1 / 5

Maryland holiday home rental

Baltimore house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £46 / night

£278 - £343 / week

1 / 6

Maryland holiday condo rental

Ocean City condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £305 / night

£2,129 / week

1 / 25

Holiday b&b in Maryland

Port Tobacco b&b

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,384 / night

£9,686 / week

1 / 5

B&b rental in Port Tobacco

Port Tobacco b&b

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £249 / night

£1,743 / week

1 / 9

Maryland holiday home rental

McHenry house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from £232 / night

£1,620 / week

1 / 20

Holiday home with swimming pool in Frederick

Frederick house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

from £176 / night

£1,231 / week

1 / 26

Holiday home in Highland

Highland house

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £84 / night

£417 - £1,000 / week

1 / 15

Maryland holiday apartment rental

Fishing Creek apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £167 / night

£778 - £940 / week

1 / 39

Holiday home in Maryland

Baltimore house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £273 / night

£1,528 / week

1 / 22

Holiday home rental

Annapolis house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from £394 / night

£2,314 - £2,995 / week

1 / 30

Holiday apartment with shared pool in Ocean City

Ocean City apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £202 / night

£1,536 - £1,577 / week

1 / 24

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Maryland holidays

Maryland's balmy coastal weather, close proximity to the nation's capital and phenomenal beaches make it an excellent place to enjoy a holiday. This small mid-coastal state is home to one of America's most beautiful bays, Chesapeake Bay. Maryland is nicknamed "America in miniature" because it offers a little of everything: urban charm, mountains, rolling plains and grasslands, crystal-clear coastal waters and a rich history. The state is also famous for its food; no holiday to Maryland is complete without sampling the fresh seafood, especially the delectable crab cakes.

Some of the many attractions and destinations in the state include:

  • Baltimore: A vibrant city on the Chesapeake Bay, Baltimore bustles with excitement and glimpses into America's storied history. Scenic Annapolis is also worth checking out if you want to take in a broader sampling of the state's urban style.
  • Chesapeake Bay: Spanning beyond Baltimore, Maryland's famous bay is a world unto itself, with outstanding fishing, swimming and sightseeing. Spectacular sunsets are a daily occurrence making Chesapeake Bay a perfect romantic getaway for couples.
  • Antietam Battlefield: The site of the single bloodiest battle in Civil War history, the Antietam Battlefield was the setting for the first Civil War battle fought in the North.
  • The Appalachian Trail: Even though the Appalachian Trail only meanders through 40 miles of Maryland, it's amongst the most beautiful and scenic stretches on the entire route.
  • Assateague Island National Seashore: Perhaps the most unique of the many Maryland National Parks, Assateague Island National Seashore is a barrier island that hosts an astonishing range of flora and fauna, including rare birds and wild ponies.

Summer is the perfect time to visit Maryland as Ocean City makes a perfect place for a family holiday. Annapolis' City Dock, which has remained virtually unchanged for a century, has summertime concerts by the shores of the Chesapeake. During the summer, you can also visit Maryland campgrounds and bring the family to one of the many water parks in Maryland.

For your accommodations, why not get a beach house if you're staying along the coast or a condo to better enjoy all the sights and sounds of the city? holiday rentals offer more room and privacy than hotels and come complete with all the comforts of home.

Maryland is also close to two of the eastern United States' most storied and popular cities: Philadelphia and Washington, DC. Both are an easy day trip from just about anywhere in the state and offer a more complete glimpse into the vibrant culture of this important corner of the country.

If you want to explore more of the area surrounding Delaware, remember that Philadelphia is only about 20 miles from downtown Wilmington. One of America's most historic and popular cities, Philadelphia makes an ideal day trip for those staying in Delaware.

Top Destination reviews

1 Bedroom/Shared Bathroom near Downtown Silver Spring MD
Perfect place for the holidays

I was really impressed with how nice this colonial home looked and how easy it was to check in with the keyless entry. It was in walking distance of the Filmore Theatre which is where I was going for a concert. The rooms were furnished nicely which included a refrigerator. … see more
Spacious Rowhome-Charm & Comfort in Patterson Park
Awesome visit

I’m so glad that we saw this Home available. Great location, amazing park just 30 seconds from home. About a 5 to 10 min drive to the inner harbor. My wife and I truly enjoyed this home. 3 floors, main living area on middle floor. Full Kitchen, dining room and living room. All bedroom are on the upper level. The lower level is not for most folks over 6 ft but a very nice and useable space,with a full laundry room.see more
Club Wyndham National Harbor Resort 2-Bedroom Condo
Great location, nice amenities, very clean rooms.

I was going to a conference in Washington, D.C. and happened to find an opening at Club Wyndam in National Harbor. It was very reasonably priced for the location. My room was upgraded to a two bedroom unit with a balcony. It was very spacious and very clean. The kitchen was very large as well! It is two blocks away from the ferris wheel on the river and there are great restaurants everywhere. This booking certainly exceeded my expectations.see more
Gorgeous Direct Oceanfront Condo, 3BR/2 BA !!!
Fantastic Getaway

The condo was fantastic! It was exactly as the listing stated. The condo was clean, check in was smooth, the view from the balcony was great. I will book the condo again for future family trips. … see more

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