Eastern Maryland Vacations

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Where to stay in Eastern Maryland

Find the best Eastern Maryland areas and neighborhoods for the activities you enjoy most. Learn more about Eastern Maryland
The morning after a frigid snow storm went through this retirement community, icy streets and a cold sky with rows of houses and christmas decorations

Ocean Pines

4.5/5(5 area reviews)

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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Eastern Maryland Hotel Deals

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
The price is ₩97,753 per night from Apr 12 to Apr 13
₩97,753
₩109,471 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (3,474 reviews)
I stayed one night there and it’s my third time I reserved this hotel, so clean, big room , bed more comfortable, friendly staff.

Reviewed on Mar 31, 2026

Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
Fully refundableReserve now, pay when you stay
The price is ₩126,571 per night from Apr 7 to Apr 8
₩126,571
₩164,528 total
Apr 7 - Apr 8
includes taxes & fees
8.8/10 Excellent! (2,365 reviews)
Room was well appointed. Had newly renovated everything. The bones of this building are older, but everything is very nice.

Reviewed on Mar 30, 2026

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
The price is ₩94,262 per night from Apr 6 to Apr 7
₩94,262
₩128,279 total
Apr 6 - Apr 7
includes taxes & fees
8.8/10 Excellent! (2,033 reviews)
It was really nice

Reviewed on Mar 29, 2026

Fenwick Inn
See all 7,937 properties in Eastern Maryland
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 Maryland

Jolly Roger Amusement Park

Jolly Roger Amusement Park

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.

Jolly Roger Amusement Park
Maryland Beach

Maryland Beach

Why not spend a carefree afternoon at Maryland Beach during your travels in Ocean City? Stroll along the seaside in this family-friendly area, or check out its lively bars.

Maryland Beach
Jolly Roger at the Pier

Jolly Roger at the Pier

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.

Jolly Roger at the Pier

Frequently asked questions

Can I cancel my flight booking to Eastern Maryland due to COVID-19?
Our helpful Customer Service Portal is your one-stop shop for most travel queries, including about flight changes and cancellations due to COVID-19. For more peace of mind, we suggest reading through the terms and conditions of your preferred airline before booking your tickets.
What's the best way to find cheap flights to Eastern Maryland that have flexible change policies?
Search for your low-cost seats to Eastern Maryland, then check the "No change fee" box below the "Flexible change policies" filter. It's that simple. We appreciate that plans can change and flexibility matters, so you can book with confidence with Expedia.
What are some of the general tips for travelers to Eastern Maryland during the COVID-19 outbreak?
If it's your first time traveling during COVID-19, you'll notice new rules and restrictions in place. Take note of these tips and make your getaway to Eastern Maryland go off without a hitch:
  • Know the rules and restrictions in both your destination and origin. You may not be able to travel depending on local circumstances, so don't forget to check before you lock something in.
  • Keep your face mask on even during airport screening. A TSA officer will ask you to adjust your mask to verify your identity.
  • Do not hand your boarding pass directly to a TSA officer. Instead, you should place the pass on the reader and then hold it up so the agent can inspect it.
  • You're allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. This will need to be taken out for screening.
  • To reduce handling during the screening process, place items such as your keys, wallet, phone and belt into your carry-on instead of into the bins.
  • Separate any food you're carrying for screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA agent to handle and inspect your belongings.

Which airlines fly to Eastern Maryland?
Southwest Airlines is a leading airline servicing Eastern Maryland. Search for airfares to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) and you'll have 5336 Southwest Airlines flights each month to pick from.
How can I find cheap tickets to Eastern Maryland?
One of the easiest ways to get your hands on cheap tickets to Eastern Maryland is to be flexible with your travel dates. Search for your flights, then click "flexible dates" at the top of your results. It'll bring up the cheapest prices for nearby days. The best price for a flight to Eastern Maryland in the last seven days was . Booking ahead will generally help you score an even better deal.
How much is a flight to Eastern Maryland?
You could have purchased a round-trip airfare to Eastern Maryland from anywhere between and in the last seven days. For one-way journeys taking off from (), the lowest price during this period was .
What are the most popular airports to fly into in Eastern Maryland?
Start organizing your Eastern Maryland escape by booking a seat on one of the 7430 flights each month to Baltimore Washington Intl. Thurgood Marshall Airport (BWI). This is the region's primary gateway.
When is the cheapest time to fly to Eastern Maryland?
Take off for Eastern Maryland early on in the week and you'll usually be rewarded with lower-priced fares. Tuesday is typically the cheapest day to jump on a plane, followed closely by Monday. If you're eager to avoid the costliest flights, steer clear of Saturdays.
How much is a plane ticket to Eastern Maryland?
In the last seven days, plane tickets to Eastern Maryland fluctuated from to .
Which airlines with flights to Eastern Maryland employ COVID-19 cleanliness policies?
Social distancing is only one small part of new travel industry strategies to help combat COVID-19. From check-in to arrival, these airlines will carry you to your destination with comfort and confidence:
  • 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.

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