Eastern Shore Vacation Packages

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Your Eastern Shore Vacation

Plan a vacation package to Eastern Shore and travel on your own terms. You'll fall in love with its nature, family-friendly attractions and history. With so many things to see and do on a trip to Eastern Shore, it can be difficult to know where to begin. Kick off your journey in Ocean City at Ocean City Boardwalk and Ocean City Beach — two popular attractions here. Another top city worth adding to your itinerary is Salisbury. Don't miss Wicomico Youth and Civic Centre and Salisbury Zoo. Whether you're planning to travel for a week or a month, Expedia are here to help you customize your next Eastern Shore vacation.

Top Eastern Shore Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The LINE Hotel DC

The LINE Hotel DC

Northwest
CA $658
per person
Oct 16 - Oct 19
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (1,006 reviews)
Holiday Inn National Airport/Crystal City by IHG

Holiday Inn National Airport/Crystal City by IHG

Crystal City
CA $713
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very good! (1,945 reviews)
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

Southwest
CA $1,596
per person
Oct 6 - Oct 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,215 reviews)
We really enjoyed our stay. The staff was wonderful. The hotel was so clean and classy. We’d definitely go again.

Reviewed on Aug 14, 2026

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crystal City
CA $886
per person
Sep 14 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very good! (1,002 reviews)
The property was extremely clean and the staff was amazing. Elevators seemed to be jacked up for our whole stay. Great convenient location. Great water pressure and good ac which is important to us.

Reviewed on Aug 10, 2026

The Poppy Georgetown

The Poppy Georgetown

Northwest
CA $1,885
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Baltimore (BWI)
9.4/10 Exceptional! (589 reviews)

Where to stay in Eastern Shore

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

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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 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
A coastal cityscape at dusk with illuminated buildings and a marina.

Sunset Island

While there might not be top attractions in Sunset Island, you can explore the larger area and discover places like Seacrets Distilling Company and Seacrets.

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Ready to book your vacation to Eastern Shore?

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Eastern Shore Hotel Deals

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD
CA $188
CA $233 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (2,628 reviews)
"Our stay overall would be given 2.5/5 stars because of the following: - Hotel Wifi coverage on our iPhones was terrible in the Atrium area and kept dropping randomly in our room. - We found a number of items in our original room that were not cleaned including beetles crawling behind the toilet. ..."

Reviewed on Aug 14, 2026

Princess Royale Oceanfront Resort
Fenwick Inn

Fenwick Inn

13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
CA $112
CA $146 total
Sep 14 - Sep 15
includes taxes & fees
8.8/10 Excellent! (2,052 reviews)
"Rooms looked amazing with the new renovations but the WiFi was horrible in the room"

Reviewed on Aug 13, 2026

Fenwick Inn
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD
Fully refundableReserve now, pay when you stay
CA $207
CA $232 total
Sep 13 - Sep 14
includes taxes & fees
9/10 Wonderful! (3,776 reviews)
"I really enjoyed my stay there...although I was surprised about the $10 per day for parking...other than that, the restaurants, poolside bar, arcade, stores, etc... that they have within the hotel was awesome...one of the best hotels I stayed in OCMD...10th floor direct oceanfront ..."

Reviewed on Aug 14, 2026

Grand Hotel Ocean City Oceanfront
See all 7,712 properties in Eastern Shore
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.
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Stay near popular Eastern Shore attractions

A vibrant amusement park with a large red Ferris wheel, a yellow roller coaster, and various colorful rides.

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 wooden pier extending into the ocean with a person standing at the end.

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 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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A wooden pier extending into calm waters, a modern building with large windows, and a clear blue sky.

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 seaside or discover the beautiful sunsets in this family-friendly area.
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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 seaside or discover the area's beautiful sunrises.
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A swimming pool with people on inflatable rings, surrounded by a grassy area and teepees.

Frontier Town Water Park and Golf

9.0/10 (2 reviews)
Bring the kiddos to Frontier Town Water Park and Golf and have a fun-filled day at this theme park in Berlin. Stroll along the seaside in this family-friendly area, or seek out the golf courses.
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Frequently asked questions

How much does an Eastern Shore vacation package cost?
Get ready to book, because a getaway to Eastern Shore starts from an affordable CA $658. When you combine your hotels, flights and car rentals into a package, you'll pick up the biggest deals.
How do I get a cheap travel package to Eastern Shore?
It's as simple as bundling. Hotels, flights and rental cars — combine whatever you need into an Eastern Shore vacation package and save. Score even more discounts when you add extras such as sightseeing tours to your booking. But that's not the only good part. You have the freedom to tailor your vacation your way. We offer more than 550 airlines and 1,000,000 hotel options worldwide, so that everyone has a chance to travel and live out those vacation dreams.
What are the top hotels in Eastern Shore?
Wingate by Wyndham Baltimore BWI Airport and Renaissance Baltimore Harborplace Hotel know how to make their guests feel at home in Ocean City. If your travel plans also include Berlin, check out Fenwick Inn and Hilton Garden Inn Ocean City Oceanfront. Both are top picks with travelers.
How far in advance should I book my Eastern Shore vacation?
Savvy travelers often reserve their seats as early as possible. You can usually start comparing international airfares on Expedia up to a year before your intended flight. If you're late to book, don't worry. Bargain prices sometimes occur just weeks prior to departure.
What does an Expedia Eastern Shore travel package include?
It all comes down to what kind of getaway you're contemplating. Eastern Shore travel deals can include car rentals, hotels and flights. You can mix and match to create the package that suits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking an Eastern Shore travel package?
A travel package can be tailored to your budget and is a great way to make your hard-earned dollars stretch further. How much you include is your call. Rental cars, hotels and flights — choose any combination that suits your style.
Can I choose my airline with an Eastern Shore Expedia vacation package?
With a vacation package, you're the boss. Whether you're eager to fly to Eastern Shore in first class or coach, simply choose from the available airline options. Expedia has access to over 550 partner airlines across the world.
If I'm not able to travel, can I cancel my Eastern Shore vacation package?
Yes, you can. We understand that things don't always go to plan, so we're here to help if you have to make changes to your Eastern Shore vacation package. It may be possible to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

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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.