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 $1,308, price is now CA $956 per person
CA $956
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
Room was clean and nicely appointed. Very comfortable stay. Would definitely return.

Reviewed on May 9, 2026

Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Price was CA $4,331, price is now CA $2,868 per person
CA $2,868
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Baltimore (BWI)
9.2/10 Wonderful! (205 reviews)
My stay at the Rosewood Hotel was absolutely wonderful from start to finish. The level of service, attention to detail, and overall atmosphere made it a truly memorable experience. From the moment I arrived, the staff was warm, welcoming, and genuinely attentive. Check‑in was smooth and effortless, and I immediately felt like a valued guest. The room was beautifully designed—spacious, spotless, and thoughtfully arranged with luxurious touches throughout. The bed was incredibly comfortable, and the overall ambiance made it easy to relax. The hotel’s amenities were equally impressive. Whether enjoying the dining options, unwinding in the lounge areas, or simply taking in the elegant décor, everything felt refined and well-curated. Every interaction with the staff felt sincere, and the service consistently exceeded my expectations. Overall, my stay at the Rosewood was exceptional. I would highly recommend this hotel to anyone looking for comfort, luxury, and top‑tier hospitality. I’m already looking forward to returning!

Reviewed on Feb 19, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $1,632, price is now CA $1,157 per person
CA $1,157
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
8.8/10 Excellent! (1,002 reviews)
Great staff and a he beds were very comfortable

Reviewed on Apr 21, 2026

Club Wyndham National Harbor

Club Wyndham National Harbor

3.5 out of 5
Price was CA $3,019, price is now CA $2,171 per person
CA $2,171
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Baltimore (BWI)
8.4/10 Very Good! (481 reviews)
Everything was top notch would differently stay again

Reviewed on Mar 9, 2026

Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was CA $1,586, price is now CA $1,147 per person
CA $1,147
per person
Jul 14 - Jul 19
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
9/10 Wonderful! (799 reviews)
great stay, would come back!

Reviewed on May 11, 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
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 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 $109 per night from May 13 to May 14
CA $109
CA $122 total
May 13 - May 14
includes taxes & fees
9/10 Wonderful! (3,567 reviews)
Overall the experience was a good one. The room was relatively clean with the exception of a few things on the floor which i just picked up. The bar on the first floor is good. The staff was friendly

Reviewed on May 11, 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 $110 per night from May 18 to May 19
CA $110
CA $143 total
May 18 - May 19
includes taxes & fees
8.8/10 Excellent! (2,061 reviews)
The Fenwick Inn is a great hotel. The manager Madison is amazing. She is extremely helpful and professional. The entire staff at the Fenwick Inn are wonderful people. I highly recommend staying at the Fenwick Inn. The hotel is clean and the location is awesome. Walking distance to the beach shopping ...

Reviewed on May 6, 2026

Fenwick Inn
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 $148 per night from May 14 to May 15
CA $148
CA $165 total
May 14 - May 15
includes taxes & fees
9/10 Wonderful! (1,625 reviews)
Yes, great hotel, great staff, great location, great clean room. Olivia the front desk rep. was Awesome.

Reviewed on May 11, 2026

Hyatt Place Ocean City / Oceanfront
See all 7,764 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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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
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 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.