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.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

Downtown Washington D.C.
CA $711
per person
Dec 22 - Dec 27
found 3 hours ago
Roundtrip flight included
Toronto (YTZ) to Baltimore (BWI)
8.8/10 Excellent! (1,009 reviews)
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.
Save 100% on your flight
CA $962
per person
Dec 22 - Dec 27
found 3 hours ago
Roundtrip flight included
Toronto (YTZ) to Baltimore (BWI)
9/10 Wonderful! (1,249 reviews)
The Mayflower Hotel, Autograph Collection

The Mayflower Hotel, Autograph Collection

Downtown Washington D.C.
CA $885
per person
Nov 2 - Nov 5
found 1 hour ago
Roundtrip flight included
Montreal (YUL) to Baltimore (BWI)
8.8/10 Excellent! (1,005 reviews)
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

Downtown Washington D.C.
Save 100% on your flight
CA $1,010
per person
Dec 22 - Dec 27
found 3 hours ago
Roundtrip flight included
Toronto (YTZ) to Baltimore (BWI)
9/10 Wonderful! (2,044 reviews)
This hotels delivers consistently good value. Beds are comfortable (not soft), bathrooms are clean and water is hot, and coffee maker in room is great, plus lounge on 2nd floor. Good location also. Suggest requesting a higher floor as neighborhood can get noisy.

Reviewed on Sep 29, 2026

The Georgetown Inn

The Georgetown Inn

Northwest
Save 100% on your flight
CA $903
per person
Dec 10 - Dec 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (1,012 reviews)
As far as I am concerned, The Georgetown Inn is the only place in the district to stay! Centrally located on Wisconsin Avenue in historic Georgetown, it is within walking distance to numerous restaurants, plenty of shopping, and access to anywhere in the entire city. I highly recommend The Georgetown Inn to everyone who is visiting the Nation’s Capitol!

Reviewed on Sep 28, 2026

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 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
A group of horses grazing on a sandy beach with sparse vegetation.

Montego Bay

If you're spending some time in Montego Bay, Northside Park and Assawoman Bay are top sights worth seeing.

Find hotels in Montego Bay

Ready to book your vacation to Eastern Shore?

Choose your dates

Eastern Shore Hotel Deals

Fenwick Inn

Fenwick Inn

13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
CA $101
CA $134 total
Oct 14 - Oct 15
includes taxes & fees
Fenwick Inn
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD
CA $98
CA $109 total
Oct 28 - Oct 29
includes taxes & fees
Grand Hotel Ocean City Oceanfront
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

4801 Coastal Highway Ocean City MD
Fully refundable
CA $95
CA $124 total
Oct 5 - Oct 6
includes taxes & fees
8.4/10 Very good! (1,009 reviews)
"The room we checked into was horrible. Clearly there had been water damage in the bathroom, and there was damage around the exterior window. The electrical was dated. There was some weird substance around the air conditioner unit, and what looked like painted over mold/mildew on the bathroom ceiling. ..."

Reviewed on Sep 28, 2026

Princess Bayside Beach Hotel
See all 7,779 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 pier with people on it, a beach, and a roller coaster in the background.

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 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 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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A vibrant amusement park with a Ferris wheel, a prize factory, and various rides and attractions.

Jolly Roger at the Pier

8.4/10 (2,874 reviews)
The old classics get a new spin at this waterfront fun park, which has an exciting collection of wild rides, high-octane roller coasters and traditional amusements.
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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 Shore vacation package cost?
Get ready to book, because a getaway to Eastern Shore starts from an affordable CA $711. 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.