Eastern Shore Holidays

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Our guide on 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
Assateague Island National Seashore showing a park and a coastal town

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.

Find hotels in Downtown Ocean City

Eastern Shore Holiday

Our pick of the best Eastern Shore Hotel Deals

Fenwick Inn

Fenwick Inn

3 out of 5
13801 Coastal Highway, Ocean City, MD
Fully refundableReserve now, pay when you stay
The price is NZ$307 per night from 28 Sept to 29 Sept
NZ$307
28 Sept - 29 Sept
includes taxes & fees
8.6/10 Excellent! (1,984 reviews)
"Always enjoy our stay at Fenwick Inn. Family friendly with the pool, hot tub and splash pad. Close to the beach, food and attractions. We will be back again."

Reviewed on 19 Sept 2025

Fenwick Inn
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street, Ocean City, MD
8.6/10 Excellent! (2,174 reviews)
"It was a great place to stay for the Event that we were in town for."

Reviewed on 19 Sept 2025

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Princess Royale Oceanfront Resort
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
2100 N Baltimore Ave, Ocean City, MD
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (3,228 reviews)
"Clean room, beach Views definitely Family friendly would book again for sure"

Reviewed on 19 Sept 2025

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Grand Hotel Ocean City Oceanfront
See all 7,735 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.

Discover the most popular places to visit in Eastern Shore

Jolly Roger Amusement Park

Jolly Roger Amusement Park

Bring your family to Jolly Roger Amusement Park and enjoy this exciting theme park in Ocean City. Amble around this family-friendly area's seaside or seek out the golf courses.

Jolly Roger Amusement Park
Roland E. Powell Convention Center

Roland E. Powell Convention Center

Learn about the events happening in 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.

Roland E. Powell Convention Center
Blackwater National Wildlife Refuge

Blackwater National Wildlife Refuge

Discover a sanctuary for birds, reptiles, amphibians and mammals on Maryland's Eastern Shore in this beautiful area rich in wetlands, forest and meadows.

Blackwater National Wildlife Refuge

Frequently asked questions

Can I cancel my flight booking to Eastern Shore due to COVID-19?
Click through to our Customer Service Portal for important details about changing your flights because of COVID-19. Also, read over the terms and conditions of the carrier you're considering before booking your journey to Eastern Shore.
What's the best way to find cheap flights to Eastern Shore that have flexible change policies?
At Expedia, we've been channeling our inner gymnast to offer you the most flexible fares in town. Just click on "No change fee" directly under the "Flexible change policies" filter to find your dream flight to Eastern Shore.
What are some of the general tips for travellers to Eastern Shore during the COVID-19 outbreak?
With the continuation of COVID-19  travelling today comes with more challenges than in the past. Have a read over these worthwhile tips before hopping on your plane to Eastern Shore:
  • Understand what rules and restrictions apply to both your destination and origin. It may not be possible to travel depending on local circumstances, so make sure you check before you lock in your flight.
  • Keep your face mask on during airport screening. A TSA officer will require you to adjust your mask for ID purposes.
  • To decrease the risk of cross-contamination, place your boarding pass on the scanner yourself and then hold it up for inspection. Do not hand your boarding pass directly to a TSA agent.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag for X-ray screening.
  • Put any personal items (phone, keys and wallet) in your carry-on rather than a bin to reduce handling during screening.
  • Separate any food you're carrying for X-ray screening. Food items often trigger the alarm. Putting them in a clear plastic bag and into a bin reduces the need for a TSA agent to touch and inspect your belongings.

Which airlines fly to Eastern Shore?
Southwest Airlines offers flights into or near Eastern Shore, including 5336 that land at Baltimore Washington Intl. Thurgood Marshall Airport (BWI) each month. Figure out your holiday dates and then lock in your seat early for an awesome deal.
How can I find cheap tickets to Eastern Shore?
Book well ahead, travel on a cheaper day, use miles or points — there's no shortage of ways! One more is to make the most of Expedia's "flexible dates" function. Find an Eastern Shore flight, then compare the prices for nearby dates. In the last seven days, the best price for a flight to Eastern Shore was .
How much is a flight to Eastern Shore?
One-way flights from () sold for as little as in the last seven days. During this period, the price of a return journey to Eastern Shore varied between and . If you find a bargain, book immediately — these fares don't stick around for long.
What are the most popular airports to fly into in Eastern Shore?
Jet into Baltimore Washington Intl. Thurgood Marshall Airport (BWI) and sample the best that Eastern Shore has to offer. As the region's main point of entry, around 7430 flights touch down here each month.
When is the cheapest time to fly to Eastern Shore?
Departing on a Tuesday, followed by a Monday, is usually the best way to nab the cheapest flight. Steer clear of the weekend if you can, because Saturday is typically the most expensive day. Spend the funds you saved living it up in Eastern Shore instead!
How much is a plane ticket to Eastern Shore?
In the last seven days, plane fares ranged between and . Take a look at our unbeatable deals to Eastern Shore, pick your favourite and get ready for your next fun holiday!
Which airlines with flights to Eastern Shore employ COVID-19 cleanliness policies?
To minimize contact between travellers and cabin crew during the COVID-19 outbreak, many airlines have taken social distancing and other precautionary measures to the skies. These carriers include:
  • Southwest Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Spirit Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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