Eastern Maryland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Holiday Inn Columbia East-Jessup by IHG

Holiday Inn Columbia East-Jessup by IHG

3 out of 5
Price was CA $1,374, price is now CA $994 per person
CA $994
per person
Sep 18 - Sep 23
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.6/10 Excellent! (1,011 reviews)
The staff were friendly and helpful. The room was clean and comfortable. There were lots of restaurants and stores near by. Check out was quick and easy.

Reviewed on Jun 24, 2026

Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was CA $1,653, price is now CA $1,133 per person
CA $1,133
per person
Sep 18 - Sep 23
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (1,000 reviews)
The staff was very friendly, and the shuttle service went above and beyond. However, my bill had a number of charges from some other guests' TV box on it. It took several calls to get my statement corrected, and I was told the TV boxes are sometimes moved to other rooms and then not reprogrammed. CHECK your TV when you arrive. If it does not have your name on it contact the front desk immediately.

Reviewed on Jun 26, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $1,577, price is now CA $1,120 per person
CA $1,120
per person
Sep 18 - Sep 23
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
6/10 (1 review)
DoubleTree by Hilton Baltimore North - Pikesville

DoubleTree by Hilton Baltimore North - Pikesville

4 out of 5
Price was CA $1,427, price is now CA $1,039 per person
CA $1,039
per person
Sep 18 - Sep 23
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8/10 Very good! (1,010 reviews)
I love everything about the property……

Reviewed on Jun 27, 2026

DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Price was CA $1,444, price is now CA $1,058 per person
CA $1,058
per person
Sep 18 - Sep 23
found 24 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.4/10 Very good! (1,168 reviews)
The front desk staff was amazing.

Reviewed on Jun 23, 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
A crowded beach with people sunbathing, swimming, and playing in the water.

North Ocean City

1 out of top 10 points of interest in this area

North Ocean City is known for its stunning beaches, and you can see some sights in the area like Ocean City Beach and Carousel Ice Skating Rink.

Find hotels in North Ocean City

Ready to book your vacation to Eastern Maryland?

 

Choose your dates

Eastern Maryland Hotel Deals

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
The price is CA $519 per night from Jul 27 to Jul 28
CA $519
CA $604 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (2,482 reviews)
"Staff very friendly and helpful, they went out of their way to help me and arrange a room on same floor as my family for our vacation"

Reviewed on Jun 27, 2026

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
The price is CA $408 per night from Jul 5 to Jul 6
CA $408
CA $457 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (3,648 reviews)
"This hotel is fantastic! All the shops and restaurants are great and everyone was so friendly and helpful. We are seniors and the location is perfect-- just far enough to walk to the Inlet and pretty quiet and family oriented.. I highly recommend this Hotel and when we come back it will be where ..."

Reviewed on Jun 27, 2026

Grand Hotel Ocean City Oceanfront
Fenwick Inn

Fenwick Inn

3 out of 5
13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Jul 1 to Jul 2
CA $226
CA $274 total
Jul 1 - Jul 2
includes taxes & fees
8.8/10 Excellent! (2,048 reviews)
"Good location near beach and shops. Disinfectant used in dog rooms was awful. Also one particularly loud dog unattended Breakfast very basic Nice rooftop bar and restaurant on grounds it might be nice hotel with pool splashpad for kids but too loud for us"

Reviewed on Jun 28, 2026

Fenwick Inn
See all 8,309 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Eastern Maryland attractions

A vibrant amusement park with a large red Ferris wheel, a yellow roller coaster, and various colorful rides.

Ocean City Boardwalk

9.0/5 (11,302 reviews)
Discover a diverse collection of specialty stores, arcades, amusements, restaurants and bars on this classic wooden boardwalk on Ocean City’s waterfront.
See properties

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.

Explore a world of travel with Expedia

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