Eastern Maryland Vacation Packages

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Your Eastern Maryland Vacation

Leave all the planning up to us with an Eastern Maryland vacation package. With everything arranged before you leave, all you need to do is relax and experience this destination's wonders to the fullest. With so many things to do and see on a trip to Eastern Maryland, it can be tricky to know where to begin. Kick off your journey in Seaford at The Hen House and Seaford Sports Complex — two much-loved attractions here. Another top city worthy of a spot on your itinerary is Joppa. Don't miss White Marsh Mall and Gunpowder Falls State Park. When you're ready to stop dreaming and start packing, Expedia will help turn your Eastern Maryland vacation into reality.

Top Eastern Maryland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was CA $988, price is now CA $660 per person
CA $660
per person
Jul 26 - Jul 29
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (790 reviews)
The room I was in was a bit weird. the bed was in the middle of the room. and the lighting was very poor in the room mostly due to the way it was set up. I'd recommend they move the furniture around again cuz this was not working for them

Reviewed on Apr 30, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $2,257, price is now CA $1,481 per person
CA $1,481
per person
Jun 12 - Jun 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
Great staff and a he beds were very comfortable

Reviewed on Apr 21, 2026

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Price was CA $1,306, price is now CA $883 per person
CA $883
per person
Jun 14 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,137 reviews)
I loved the indoor pool. The sign outside is perfect for pictures

Reviewed on May 2, 2026

The Westin DC Downtown

The Westin DC Downtown

4 out of 5
Downtown Washington D.C.
Price was CA $958, price is now CA $677 per person
CA $677
per person
Jul 26 - Jul 29
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,006 reviews)
I would highly recommend this hotel to anyone. The staff are nice and helpful when we had questions. The staff at Root &Vine when we order pizza's to take back to our room. The sercurity guards in the lobby would always say hi and ask how you are doing. The room was amazing and we enjoyed the view from our room.

Reviewed on Apr 10, 2026

The Melrose Georgetown Hotel

The Melrose Georgetown Hotel

4 out of 5
Northwest
Price was CA $1,036, price is now CA $738 per person
CA $738
per person
Jun 14 - Jun 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,373 reviews)
Very nicely place located by George Town in walking distance of White House also

Reviewed on Apr 25, 2026

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
Wild horses hanging out on the beach, Assateague Island, Worcester County, Maryland.

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

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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 CA $115 per night from May 10 to May 11
CA $115
CA $129 total
May 10 - May 11
includes taxes & fees
9/10 Wonderful! (3,525 reviews)
Room was very clean and housekeeping emptied the garbage and restocked towels everday

Reviewed on May 3, 2026

Grand Hotel Ocean City Oceanfront
Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

3 out of 5
1 16th Street Ocean City MD
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from May 12 to May 13
CA $136
CA $152 total
May 12 - May 13
includes taxes & fees
9/10 Wonderful! (1,604 reviews)
Yes everything was amazing

Reviewed on May 3, 2026

Hyatt Place Ocean City / Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
The price is CA $403 per night from May 30 to May 31
CA $403
CA $473 total
May 30 - May 31
includes taxes & fees
8.8/10 Excellent! (2,413 reviews)
The property was in an ideal spot and did their thing for the mini vacation I had while attending a work conference!

Reviewed on May 3, 2026

Princess Royale Oceanfront Resort
See all 8,097 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.
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Discover the most popular places to visit in Eastern Maryland

Ocean City Boardwalk

Ocean City Boardwalk

4/5(15 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 Boardwalk
Ocean City Beach

Ocean City Beach

4.5/5(11 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.

Ocean City Beach
Northside Park

Northside Park

Enjoy the beautiful sunrises and explore Northside Park, a lovely green space in Ocean City. Wander the beautiful beaches and seaside in this family-friendly area.

Northside Park

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