Eastern Shore Maryland (249) Filter Cancel
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Ocean City Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
Dishwasher • Microwave • Washer/Dryer
About OUR PLACE @THE BEACH 205- B This two bedroom, two bath condo is spacious and nicely decorated. This unit overlooks the wetlands and the bay and has a beautiful view of the sunset. Bay side complex, just 3 ...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
About MARINER II 2M Direct Ocean Front unit in a small building, well furnished and supplied. Mid town location , close to restaurants and shopping. MARINER II 2M comes with following features and amenities: cen...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
2 BR / 2 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Nicely furnished oceanfront condo, features large living room, dining room, and kitchen combo, a large master bedroom en- suite with king- size bed and separate balcony entrance, guest bedroom with queen size bed an...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
1 BR / 1 BA / Sleeps 3 1 3 Min stay varies
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
About BLUEWATER EAST 203S This property is on a low floor and overlooks the outdoor pool. BLUEWATER EAST 203S comes with following features and amenities: central air conditioning, fee based building wifi interne...
(1) Excellent (1 review)
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Ocean City Condo
1 BR / 2 BA / Sleeps 3 1 3 3 night min stay
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 2 bathrooms Sleeps 3
Microwave • Washer/Dryer • Air Conditioning
BONNIE BELL 308 comes with following features and amenities: unit air conditioning, washer and dryer, heat, 2 bathrooms, iron & board, cable TV, balcony facing west, refrigerator, dishwasher, microwave, coffee ...
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Ocean City Apartment
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Apartment / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • Washer/Dryer
Located in one of Ocean city's most prestigious buildings, this 2 bedroom, 2 bath direct oceanfront condo, with enclosed balcony, is located on the third floor and is completely remodeled. New kitchen and baths extre...
(11) Excellent (11 reviews)
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
3 BR / 2 BA / Sleeps 9 3 9 7 night min stay
Condo / 3 Bedrooms / Sleeps 9
3 bedrooms 2 bathrooms Sleeps 9
Dishwasher • Microwave • Washer/Dryer
About SEA RAIDER 302 This ocean block unit has a fully equipped kitchen. Just steps to the beach. Ocean block small building just steps to the beach. One car parking and non- smoking units and no- pet allowed. Mid...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Inexpensive condo with a million dollar view of the Assawoman Bay. Easy walk to the Ocean Beach and The Hilton. In the middle of everything. Can dock your boat and fish off pier. Dogs are welcome for a $150 fee. Bay ...
(2) Excellent (2 reviews)
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
1 BR / 1 BA / Sleeps 3 1 3 7 night min stay
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
Dishwasher • Microwave • Washer/Dryer
About BRADLEY ON THE BAY 233- G "Delightful End Unit with private balcony on the second floor. Unit offers a King Size bed and fully equipped kitchen. Just one block to the beach with a beautiful view of the bay and p...
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Ocean City Condo
1 BR / 1 BA / Sleeps 3 1 3 3 night min stay
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
About Bluewater East 901- N One Block To Ocean, Nice Outdoor Pool And Separate Kiddie Pool Bluewater East 901- N Comes With Following Features And Amenities: Central Air Conditioning, Fee Based Building Wifi Inte...
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Ocean City Condo
1 BR / 1 BA / Sleeps 3 1 3 7 night min stay
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Microwave • Washer/Dryer
About OCEAN BEACH D- 2 First floor unit located directly on the boardwalk. Features a porch to relax and watch the people. OCEAN BEACH D- 2 comes with following features and amenities: unit air conditioning, wash...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Microwave • Washer/Dryer
About CLUB OCEAN VILLA II 99 Amenities CLUB OCEAN VILLA II 99 comes with following features and amenities: central air conditioning, wifi internet, washer and dryer, 2 bathrooms, cable TV, balcony facing north...
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Ocean City Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
About SURFCASTER 202 Large unit with wrap round balcony looking east with side view of the ocean. Non- smoking and no pets allowed in the unit. Direct ocean front lower- rise masonry building located on 64th stree...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
3 BR / 3 BA / Sleeps 10 3 10 Min stay varies
Condo / 3 Bedrooms / Sleeps 10
3 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Explore Ocean City While Staying in the Meridian Vacation Rental When visiting Ocean City, Maryland, the Meridian vacation rental is an affordable way to take a luxurious vacation. Tourists come from all over to exp...
(1) Excellent (1 review)
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Condo / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Oceanfront Building With Bayview! This Three Bedroom, Two Bath Condo Is Located In An Oceanfront Building So You Are Steps To The Beach. Unit Has A Very Large Balcony That Offer Fantastic Sunsets. Fully Equipped Kitche...
Ocean City Maryland Vacation Rentals - Apartment
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Ocean City Apartment
Studio / 1 BA / Sleeps 1 0 1 No min stay
Apartment / Studio / Sleeps 1
Studio 1 bathroom Sleeps 1
High Speed Internet • Dishwasher • Microwave
Ideally located on the beautiful Ocean City Beach, this hotel is located just minutes away from local attractions such as the Assateague Island National Seashore, Ocean Downs Racetrack and the Ocean City Boardwalk. The...
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Ocean City Condo
3 BR / 2 BA / Sleeps 9 3 9 7 night min stay
Condo / 3 Bedrooms / Sleeps 9
3 bedrooms 2 bathrooms Sleeps 9
Dishwasher • Microwave • Washer/Dryer
About SPINNAKER 11 Direct ocean front unit with limited view of the ocean. Beautiful remodel unit, perfect for a big family. Ocean Front low- rise building, located mid- town close to Indoor Golf on 67 street an...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
1 BR / 1 BA / Sleeps 3 1 3 3 night min stay
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
High Speed Internet • Dishwasher • Microwave
About Ponte Vista 513 Nice Building, bay front, Bright Souther exposure balcony on fifth floor overlooking the outdoor pool and 40" TV in living room. Ponte Vista 513 comes with following features and amenities:...
(1) Excellent (1 review)
Ocean City Maryland Vacation Rentals - Townhouse
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Ocean City Townhouse
4 BR / 3.5 BA / Sleeps 14 4 14 Min stay varies
Townhouse / 4 Bedrooms / Sleeps 14
4 bedrooms 3.5 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
Are you looking to spend your next vacation in a spacious rental with many of the amenities of home? Our 4 story townhomes can accomodate large groups up to 14 people and provide easy access to the beach. They are locate...
(23) Excellent (23 reviews)
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
OUR PLACE @THE BEACH 202- I comes with following features and amenities: 2 bathrooms, central air conditioning, washer and dryer, cable TV, refrigerator, dishwasher, microwave, coffee maker, toaster, disposal, ...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
1 BR / 1 BA / Sleeps 3 1 3 7 night min stay
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
Dishwasher • Microwave • Washer/Dryer
About BEACHLOFT 1L First elevated floor unit, direct ocean front with a distracted view of the ocean. End unit bright and clean. This ocean front mid- rise is one of the most requested by Ocean City vacationers. ...
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Ocean City Home
4 BR / 2.5 BA / Sleeps 10 4 10 Min stay varies
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 2.5 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
This amazing property is located on the bayside very convenient to the beach, bayside dining, shopping, entertainment, fishing, boating, nightlife
(5) Excellent (5 reviews)
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
2 BR / 2 BA / Sleeps 5 2 5 Min stay varies
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
Dishwasher • Microwave • Washer/Dryer
About Lost Colony III 221 Nice two bedroom, bayside about 6 blocks to the Ocean. Features outdoor pool and attractive furniture. Unit has WIFI and two tv's. Lost Colony III 221 comes with following features and a...
Entrance Mural
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Ocean City Condo
3 BR / 2 BA / Sleeps 10 3 10 3 night min stay
Condo / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Watch sunrise and sunset from the condo! Watch ocean from the balcony, master bedroom and the living room! Enjoy the sound of the waves! Large condo, located directly on the beach in Ocean City, MD. Enjoy Sunset fr...
(5) Excellent (5 reviews)
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Ocean City Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Microwave • Air Conditioning
Enjoy the waves without shrinking your wallet. Spacious 2 & 3 bedroom units only one block from the beach! The condo is located on the ocean side in the Northern part of Ocean City. This side of Ocean City is great ...
(5) Very Good (5 reviews)
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
3 BR / 2 BA / Sleeps 9 3 9 3 night min stay
Condo / 3 Bedrooms / Sleeps 9
3 bedrooms 2 bathrooms Sleeps 9
High Speed Internet • Dishwasher • Microwave
About KING GEORGE CONDO 710D Boat dock in front of unit. Also features high speed internet. KING GEORGE CONDO 710 D comes with following features and amenities: central air conditioning, free wifi internet, wash...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Condo / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
About OUR PLACE @THE BEACH 304- B Beautifully remodeled two bedroom two bedroom condo with a bay front view. Close to the pool and near the entrance for a short walk to the beach. Three flat screen TV's with new floor...
Ocean City Maryland Vacation Rentals - Condo
1 / 20

Ocean City Condo
3 BR / 2 BA / Sleeps 10 3 10 7 night min stay
Condo / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
About FLYING CLOUD 807 Large end unit with great view of ocean. Also features a rear balcony offering a view of the bay. Very attractive unit. This building features wireless internet access for a fee. Amenities ...
Ocean City Maryland Vacation Rentals - Condo
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Ocean City Condo
1 BR / 1.5 BA / Sleeps 6 1 6 Min stay varies
Condo / 1 Bedroom / Sleeps 6
1 bedrooms 1.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This condo is in a really unique building called the Pyramid, located directly on the beach with a heated pool. The unit is meticulously maintained to offer renters a comfortable, clean vacation it offers 1 1/2 baths, ...
(14) Excellent (14 reviews)
Ocean City Maryland Vacation Rentals - Condo
1 / 12

Ocean City Condo
1 BR / 1 BA / Sleeps 3 1 3 7 night min stay
Condo / 1 Bedroom / Sleeps 3
1 bedrooms 1 bathroom Sleeps 3
Dishwasher • Microwave • Washer/Dryer
This one bedroom unit is very attractive. Fully equipped kitchen. Large private balcony with a view of the bay and pool. On bay side next to Convention Center and one block to the beach when you cross Coastal Hwy. Th...
(1) Excellent (1 review)
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About Eastern Shore

A beautiful coastal respite, Maryland’s Eastern Shore is the ideal place to escape from the hubbub of Washington, D.C. Choose from dozens of waterfront Eastern Shore vacation rentals, and plan your perfect getaway on the beach.

Climate

A true summer hotspot, Maryland’s Eastern Shore heats, with temperatures topping out around 90 degrees in the summer months of July and August. Winters tend to be moderate, with temperatures in the 40s. Those who want to enjoy fun in the sun should visit in the summer, while those looking for a quiet yet scenic respite should visit in the shoulder seasons of spring and fall.

Transit

The perfect location for an Atlantic road trip, Maryland’s eastern shore is best reached by car. Many visitors fly to one of the nearby Baltimore or Washington, D.C. airports and drive across the Chesapeake Bay Bridge to get to the area. Use your Eastern Shore vacation rental as a base for exploring, and travel from north to south on Highway 50, the main artery through the area.

Things to Do

If you’re seeking a tranquil spot on the shore, Cambridge and Easton offer small town charm with plenty of culture and nature to explore. During the day, make a trip to Blackwater National Wildlife Refuge, just south of Cambridge. Hike the Marsh Edge Trail or the Tubman Road Trail to see brackish marshes and bald eagles, or canoe one of the Water Trails for a new perspective of the Eastern Shore.
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If you’re a nature lover, don’t miss Easton’s Pickering Creek Audubon Center, a 400-acre working farm that features four miles of hiking trails, bird watching areas, canoeing, and kid-friendly activities. In the evening, catch a performance at Easton’s Avalon Theatre, a historic performance space that hosts a range of traditional and contemporary singers and musicians.

Learn more about the Eastern Shore’s seafaring history in St. Michaels, home of the Chesapeake Bay Maritime Museum. Here visitors can see a working boatyard, try their hand at catching crabs at the wharf, immerse themselves in the area’s oystering industry, and learn about the St. Michaels steamboat building history.

For some quality time on the sand, head east to Ocean City. This fun-filled beach town has everything from long stretches of sand to a family-friendly boardwalk and seasonal events. Swim in the Atlantic waves, shop for souvenirs along the Ocean City Boardwalk, and catch a summer concert.

Food

Thanks to its coastal location, Maryland’s Eastern Shore is a great place to find deliciously fresh seafood. For some of the freshest crab, try Hooked in Ocean City, which serves up everything from crab bisque to gourmet crab cakes. In St. Michaels, look no further than Waterman’s Crab House, which features crab pots and crab feasts with harbor views and live music. Other tasty and traditional regional fare includes fried clams, oyster fritters and Chicken Chesapeake. For dessert, treat the family to a slice of Smith Island Cake, a seven-layer cake that is also the official cake of Maryland.

Events

Although the warmer months may draw the largest crowds to the region, tourists willing to brave the colder months will still find plenty of fun, local festivals and events to enjoy, including:

  • WineFest at St. Michaels (April): A weekend festival that features local wine tastings, regional dishes from area chefs, and a variety of talented artists.
  • National Hard Crab Derby (September): The crab-themed event features crab races, crab cooking and picking contests, carnival rides, beauty pageants, live entertainment, a parade and much more. The festival runs for an entire weekend and is a unique way to celebrate the region.
  • Tilghman Day (October): As an annual festival celebrating Maryland’s seafood industry, this event includes oyster shucking and crab picking contests, as well as live music, vendors, and an auction. 
  • The Waterfowl Festival (November): Perfect for families that enjoy wildlife and the outdoors, this festival draws approximately 15,000 people annually and offers a variety of vendors and exhibitionists.


Whether you’re seeking a tranquil escape from the city or a fun beach getaway, the Chesapeake Bay has what you’re looking for. Book your Eastern shore condos before the season heats up, and enjoy beautiful views, fascinating history, and legendary food.