Eastern Maryland Vacations from ￥269,702

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The Latest Eastern Maryland Vacation Packages

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

The Windsor Suites

Center City
￥269,702
per person
Dec 23 - Dec 30
found 24 hours ago
Roundtrip flight included
Osaka (OSA) to Philadelphia (PHL)
8.8/10 Excellent! (3,295 reviews)
Hotel room was dirty. Dust everywhere, someone’s food still in fridge.

Reviewed on Oct 13, 2026

YOWIE (Hotel & Shop)

YOWIE (Hotel & Shop)

South Philadelphia
￥438,369
per person
Nov 14 - Nov 21
found 13 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Philadelphia (PHL)
9.8/10 Exceptional! (76 reviews)
The Rittenhouse Philadelphia

The Rittenhouse Philadelphia

Center City
￥442,191
per person
Dec 23 - Dec 30
found 24 hours ago
Roundtrip flight included
Osaka (OSA) to Philadelphia (PHL)
9.4/10 Exceptional! (1,004 reviews)
Chic & Cozy Philly Stay in City Center

Chic & Cozy Philly Stay in City Center

South Philadelphia
￥353,355
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip flight included
Osaka (OSA) to Philadelphia (PHL)
8.4/10 Very Good! (7 reviews)
Little trouble getting in but host was responsive despite the late hour. I would have appreciated a more accurate description of the parking situation. Not only is there no parking on site, there is no parking anywhere close. The place is nice and roomy.

Reviewed on Aug 2, 2026

Hyatt Centric Rittenhouse Square Philadelphia

Hyatt Centric Rittenhouse Square Philadelphia

Center City
￥306,869
per person
Dec 23 - Dec 30
found 24 hours ago
Roundtrip flight included
Osaka (OSA) to Philadelphia (PHL)
9.4/10 Exceptional! (1,773 reviews)
It was okay. Room was nice. Food was overpriced for what you get.

Reviewed on Oct 12, 2026

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.

Find hotels in Downtown Ocean City
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

North Ocean City is known for its stunning beaches, and you can see some sights in the area like Ocean City Beach and Carousel Ice Skating Rink.

Find hotels in North Ocean City
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

Midtown Ocean City is beloved for its stunning beaches. Take some time to explore sights in the area like Ocean City Beach and Seacrets Distilling Company.

Find hotels in Midtown Ocean City
A beach with a clear sky and calm sea.

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.

Find hotels in Ocean Pines
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.

Find hotels in West Ocean City

Find the Best Eastern Maryland Vacation Packages

Eastern Maryland Hotel Deals

Castle in the Sand

Castle in the Sand

3701 Atlantic Avenue Ocean City MD
￥11,993
￥13,433 total
Oct 14 - Oct 15
includes taxes & fees
Castle in the Sand
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
￥10,217
￥11,443 total
Nov 1 - Nov 2
includes taxes & fees
Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD
￥13,834
￥18,016 total
Oct 14 - Oct 15
includes taxes & fees
8.8/10 Excellent! (2,848 reviews)
"Our stay was excellent, definitely will go back!"

Reviewed on Oct 13, 2026

Princess Royale Oceanfront Resort
See all 8,000 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.

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.
See properties
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.
See properties
A stone wall with the text "Roland E. Powell Convention Center" and a landscaped area with trees and shrubs.

Roland E. Powell Convention Center

8.0/10 (2,358 reviews)
Learn about the events happening at Roland E. Powell Convention Center during your trip to Ocean City. Stroll along the beautiful beaches or discover the beautiful sunrises in this family-friendly area.
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A beach with people, umbrellas, and sand.

Maryland Beach

9.0/10 (5,506 reviews)
Why not spend a carefree afternoon at Maryland Beach during your travels in Ocean City? Stroll along the seaside in this family-friendly area, or check out its lively bars.
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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)
Explore the lovely green spaces of Inlet Park and enjoy the golf courses in Ocean City. Stroll along the beautiful beaches or discover the area's beautiful sunrises.
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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)
Bring your family to Jolly Roger Amusement Park and have a fun-filled day at this theme park in Ocean City. Amble around this family-friendly area's seaside, or seek out the golf courses.
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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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Frequently asked questions

How much does an Eastern Maryland vacation package cost?
Chart your own course with our Eastern Maryland vacation packages, which start from only ￥269,702. Pick the hotels and flights that fit your travel plans. Then, add on one or two tours or experiences for a one-of-a-kind getaway.
How do I get a cheap travel package to Eastern Maryland?
It's as simple as bundling. Flights, rental cars and hotels — combine whatever you need into an Eastern Maryland vacation package to save tons of cash. Score even more discounts when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the freedom to tailor your trip your way. We offer more than 550 partner airlines and 1,000,000 hotels worldwide, so that everyone has a chance to travel and live out those vacation fantasies.
What are the top hotels in Eastern Maryland?
For properties in Ocean City with comfy beds and friendly service, you can't go past Wingate by Wyndham Baltimore BWI Airport and Renaissance Baltimore Harborplace Hotel. If you're swinging by Selbyville as well, you can look forward to a wonderful night's sleep at Fenwick Inn or Hilton Garden Inn Ocean City Oceanfront.
How far in advance should I book my Eastern Maryland vacation?
It's hard to pick the perfect time for airfares, but we generally say the earlier, the better. Many international journeys on Expedia become available to compare up to a year in advance. If you're booking late, fear not. Bargain prices occasionally appear within a few weeks of departure dates.
What does an Expedia Eastern Maryland travel package include?
That depends on what type of escape you're thinking about. Eastern Maryland travel deals can include flights, hotels and car rentals. You can mix and match to find the bundle that suits your style and budget. You can also add on experiences and activities after you've booked to land even bigger discounts.
What should I know before booking an Eastern Maryland travel package?
When you book your hotels, flights and car rentals together, you'll walk away with incredible discounts. Whether you're organizing a beach break in a villa or want to stay in a fancy hotel in the city, Expedia can make it happen for less.
Can I choose my airline with an Eastern Maryland Expedia vacation package?
You can, and with more than 550 airlines to select from throughout the world, it's all about choice. Look through the available options and see which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my Eastern Maryland vacation package?
We understand — life sometimes gets in the way of your plans. If you've locked in an Eastern Maryland vacation package and have to change or cancel it, we can help. We suggest visiting our Customer Service Portal first for information. But in general, if you've booked your package in the last 24 hours, you may be able to cancel and rebook at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.