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.
Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Price was CA $960, price is now CA $758 per person
CA $758
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
No reviews
Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
Price was CA $1,455, price is now CA $992 per person
CA $992
per person
Jun 13 - Jun 17
found 1 hour ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
7.6/10 Good! (1,006 reviews)
Everything was amazing the only issue I had was Expedia over booked. Karen was such a help on the matter. She was friendly, patient, & accommodating. She helped to make my trip amazing so grateful for her!

Reviewed on Apr 16, 2026

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Price was CA $2,173, price is now CA $1,548 per person
CA $1,548
per person
Jun 19 - Jun 22
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9.8/10 Exceptional! (59 reviews)
We absolutely loved staying at this hotel. The room was clean, comfortable, and the decor was awesome. The hotel staff was very friendly and accommodating. The location is great, walking distance to cute coffee shops, restaurants, and shops. Overall, loved our stay!

Reviewed on Mar 22, 2026

Landing Furnished Apartments - Alexandria

Landing Furnished Apartments - Alexandria

4 out of 5
Old Town West
Price was CA $1,844, price is now CA $1,348 per person
CA $1,348
per person
Jun 11 - Jun 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
No reviews
The property was as listed and check in and checkout were both very easy. Communication was also very good as we received quick responses to all questions.

Reviewed on Apr 3, 2026

Elegant 2BR Apartment - Minutes to D.C.

Elegant 2BR Apartment - Minutes to D.C.

3.5 out of 5
Crystal City
Price was CA $1,944, price is now CA $1,489 per person
CA $1,489
per person
Jun 13 - Jun 17
found 1 hour ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9.8/10 Exceptional! (7 reviews)

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
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

Ready to book your vacation to Eastern Shore?

 

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Eastern Shore 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 $95 per night from Apr 21 to Apr 22
CA $95
CA $106 total
Apr 21 - Apr 22
includes taxes & fees
9/10 Wonderful! (3,527 reviews)
It was just what I needed. Ocean front 10th floor and quiet, sunny days and nights.

Reviewed on Apr 16, 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 CA $150 per night from Apr 30 to May 1
CA $150
CA $189 total
Apr 30 - May 1
includes taxes & fees
8.8/10 Excellent! (2,385 reviews)
We love staying here for staycations

Reviewed on Apr 15, 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 CA $78 per night from Apr 28 to Apr 29
CA $78
CA $107 total
Apr 28 - Apr 29
includes taxes & fees
8.8/10 Excellent! (2,038 reviews)
Great services

Reviewed on Apr 15, 2026

Fenwick Inn
See all 7,652 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Eastern Shore

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
Carousel Ice Skating Rink

Carousel Ice Skating Rink

Enjoy a trip to Carousel Ice Skating Rink and popular activities like golfing in Ocean City. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

Carousel Ice Skating Rink

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.