Eastern Shore Vacations from $275
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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 Center 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.
The Latest Eastern Shore vacation packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Laurel
West Laurel
Save 100% on your flight
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.2/10 Very Good! (1,000 reviews)
I really enjoyed my stay. Staff was excellent. It was quite and very comfortable
Reviewed on Jul 27, 2025
Hampton Inn & Suites Baltimore Inner Harbor
Downtown Baltimore
Save 100% on your flight
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
8.6/10 Excellent! (1,001 reviews)
Every employee we met was kind and helpful Honestly best sleep we all had in a while! Nice pool. Good breakfast. Nice spacious room. We could walk easily to the water and there is so much to do there! Will be back!
Reviewed on Aug 11, 2025
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See all available trips from Columbus to Eastern Shore
View all tripsWhere to stay in Eastern Shore
Find the best Eastern Shore areas and neighborhoods for the activities you enjoy most. Learn more about Eastern Shore
Downtown Ocean City
1 out of top 10 points of interest in this area
If you're spending some time in Downtown Ocean City, Ocean City Beach and Ripley's Believe It or Not! are top sights worth seeing.
Discover the most popular places to visit in Eastern Shore
Ocean City Boardwalk
4.5/5(1,896 reviews)
Discover a diverse collection of specialty stores, arcades, amusements, restaurants and bars on this classic wooden boardwalk on Ocean City’s waterfront.
Ocean City Beach
4.5/5(1,615 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.
Jolly Roger Amusement Park
4/5(318 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.
Eastern Shore Hotel Deals
Princess Royale Oceanfront Resort
Oceanfront on 91st Street, Ocean City, MD
$139 nightly
The price is $153 total per night from Sep 7 to Sep 8
$153 total
Sep 7 - Sep 8
Total includes taxes and fees
8.4/10 Very Good! (1,989 reviews)
"We love the gorgeous atrium pool!!"
Reviewed on Aug 9, 2025
Fenwick Inn
13801 Coastal Highway, Ocean City, MD
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $114 total per night from Sep 8 to Sep 9
$114 total
Sep 8 - Sep 9
Total includes taxes and fees
8.6/10 Excellent! (1,970 reviews)
"The hotel was nice. Close to many restaurants"
Reviewed on Aug 11, 2025
Grand Hotel Ocean City Oceanfront
2100 N Baltimore Ave, Ocean City, MD
$177 nightly
The price is $195 total per night from Sep 1 to Sep 2
$195 total
Sep 1 - Sep 2
Total includes taxes and fees
9/10 Wonderful! (3,089 reviews)
"Appreciated hanging out on our balcony to watch the sturgeon moon rise. Always so enjoy being so close to the ocean. I could go back and forth from the room to the beach so easily while my husband (who is not a sand lover) can relax while I play"
Reviewed on Aug 11, 2025
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.