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
Historic Inns of Annapolis
Hotel Indigo Baltimore Downtown by IHG
Pier 5 Hotel Baltimore
Hampton Inn & Suites Baltimore Inner Harbor
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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

Discover the most popular places to visit in Eastern Shore

Eastern Shore Hotel Deals

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
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

Princess Royale Oceanfront Resort
Fenwick Inn

Fenwick Inn

3 out of 5
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

Fenwick Inn
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
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

Grand Hotel Ocean City Oceanfront
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.