Eastern Maryland Vacation Packages 2026 from $649

Your Eastern Maryland Vacation

Leave all the planning up to us with an Eastern Maryland vacation package. With everything arranged before you leave, all you need to do is relax and experience this destination's wonders to the fullest. With so many things to do and see on a trip to Eastern Maryland, it can be tricky to know where to begin. Kick off your journey in Seaford at The Hen House and Seaford Sports Complex — two much-loved attractions here. Another top city worthy of a spot on your itinerary is Joppa. Don't miss White Marsh Mall and Gunpowder Falls State Park. When you're ready to stop dreaming and start packing, Expedia will help turn your Eastern Maryland vacation into reality.

The Latest Eastern Maryland vacation packages

Price found within the past 48 hours. Click for updated prices.

Club Quarters Hotel White House, Washington DC

Downtown Washington D.C.

Save 100% on your flight

$649

per person

Nov 13 - Nov 17

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9/10 Wonderful! (2,093 reviews)

Tudor Lux

$2,508

per person

Dec 2 - Dec 5

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Philadelphia (PHL)

No reviews

Casa De Miliki

South Philadelphia

$6,450

per person

Dec 13 - Dec 20

found 2 hours ago

Roundtrip flight included

San Juan (SJU) to Philadelphia (PHL)

No reviews

Tudor Place

Save 100% on your flight

$2,208

per person

Dec 2 - Dec 5

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Philadelphia (PHL)

No reviews

Orchard Way

Save 100% on your flight

$1,704

per person

Dec 2 - Dec 5

found 1 day ago

Roundtrip flight included

San Juan (SJU) to Philadelphia (PHL)

No reviews

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Where to stay in Eastern Maryland

Find the best Eastern Maryland areas and neighborhoods for the activities you enjoy most. Learn more about Eastern Maryland

A Ferris wheel, a roller coaster, and a building with a sign that reads 'Holy Roller.'

Downtown Ocean City

2 out of top 10 points of interest in this area

If you're spending some time in Downtown Ocean City, Ocean City Beach and Jolly Roger at the Pier are top sights worth seeing.

A crowded beach with people sunbathing, swimming, and playing in the water.

North Ocean City

1 out of top 10 points of interest in this area

A pretty shoreline, miniature golf, watersports and seafront accommodations make this a great spot for a fun-filled summer vacation.

A Ferris wheel, a carousel, and a food stall at a fair.

Midtown Ocean City

2 out of top 10 points of interest in this area

Relax on golden sands, dabble in watersports, enjoy family-friendly amusements and play mini golf at this attractive coastal suburb.

Ocean Pines

Boasting the largest concentration of retirees on the Eastern Shore, this community offers the Ocean Pines Golf Club, designed by Robert Trent Jones, and 13 parks, including White Horse Park. Enjoy golfing, park visits, and a peaceful atmosphere.

A marina with multiple sailboats docked.

West Ocean City

Discover fishing charters, boating, and marinas in this census-designated area, located across the Sinepuxent Bay from Ocean City. Shop at Outlets Ocean City and easily access the beach resort town via the Harry W. Kelley Memorial Bridge.

Stay near popular Eastern Maryland attractions

A boardwalk entrance with a sign reading "Boardwalk Maryland" and two lighthouse-style structures.

Ocean City Boardwalk

9.0/10 (11,302 reviews)

Discover a diverse collection of specialty stores, arcades, amusements, restaurants and bars on this classic wooden boardwalk on Ocean City’s waterfront.

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A coastal cityscape with a sandy beach, ocean waves, and high-rise buildings.

Ocean City Beach

9.2/10 (10,973 reviews)

Swim in the waves of the Atlantic Ocean, relax on soft white sands or stroll by the arcades and shops on the exciting boardwalk at this family-friendly city beach.

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A beach with people, umbrellas, and sand.

Maryland Beach

9.0/10 (5,506 reviews)

Sun, sand and surf lures visitors to the northernmost section of Ocean City’s 10-mile (16-kilometer) long Atlantic coastline.

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Roland E. Powell Convention Center

8.0/10 (2,358 reviews)

You can always find something exciting to see or do at this entertainment complex in the heart of Ocean City, with major music concerts and events.

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A wooden boardwalk by a body of water with binoculars and a bench.

Inlet Park

8.6/10 (1,457 reviews)

Admire the views from this boardwalk park, study an artistic totem pole, watch fishers, browse quirky shops and visit a museum about life saving.

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A carousel, a large statue, and a building with a neon sign.

Jolly Roger Amusement Park

8.2/10 (3,806 reviews)

From child-friendly attractions and a thrilling roller coaster to miniature golf, karting and waterslides, there’s no end to the entertainment at this theme park.

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Ripken Stadium

8.8/10 (165 reviews)

Catch an event at Ripken Stadium during your trip to Aberdeen. You can attend a baseball game while in the area.

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Salisbury University

8.4/10 (452 reviews)

Take a campus tour or just explore the area of Salisbury University, during your trip to Salisbury. While you're in the area, stroll along the beautiful beaches.

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Eastern Maryland Hotel Deals

Castle in the Sand

3701 Atlantic Avenue Ocean City MD

$84 nightly

$94 total

Oct 13 - Oct 14

Total with taxes and fees

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD

Fully refundableReserve now, pay when you stay

$64 nightly

$72 total

Nov 1 - Nov 2

Total with taxes and fees

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD

$108 nightly

$119 total

Oct 18 - Oct 19

Total with taxes and fees

8.8/10 Excellent! (2,842 reviews)

"Several family members stayed here for a wedding in the area. Our suites were very nice. The full size refrigerator and even the stove came in very handy. The living area, bathroom and bedroom were roomy and comfortable. Would definitely stay here again."

Reviewed on Oct 12, 2026

See all 7,956 properties in Eastern Maryland

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.