Eastern Shore Vacation Packages

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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 Centre 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.

Top Eastern Shore Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,044, price is now CA $824 per person
CA $824
per person
Aug 23 - Aug 26
found 24 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
8.2/10 Very good! (1,001 reviews)
Property was very nice, room was very clean.

Reviewed on Jun 27, 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 1 day 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

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 1 day 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

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 1 day 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

Holiday Inn Express Hotel & Suites Columbia East - Elkridge by IHG

Holiday Inn Express Hotel & Suites Columbia East - Elkridge by IHG

2.5 out of 5
Price was CA $1,398, price is now CA $1,101 per person
CA $1,101
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Baltimore (BWI)
8.6/10 Excellent! (1,015 reviews)
Staff was helpful. A primary reasons we booked was because of the pool which was closed.

Reviewed on Jun 22, 2026

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
A Ferris wheel, a roller coaster, and a building with a sign that reads 'Holy Roller.'

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 Jolly Roger at the Pier are top sights worth seeing.

Find hotels in Downtown Ocean City

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Eastern Shore 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! (2,049 reviews)
"Making of the room."

Reviewed on Jun 28, 2026

Fenwick Inn
See all 7,970 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.
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Stay near popular Eastern Shore 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 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 travelers to Eastern Shore during the COVID-19 outbreak?
With the continuation of COVID-19, traveling 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 vacation 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 favorite and get ready for your next fun vacation!
Which airlines with flights to Eastern Shore employ COVID-19 cleanliness policies?
To minimize contact between travelers 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.

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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.