Eastern Shore Vacation Packages 2026 from $324

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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 Center 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.

The Latest Eastern Shore vacation packages

Price found within the past 48 hours. Click for updated prices.

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crystal City

Save 100% on your flight

$324

per person

Dec 27 - Dec 31

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.2/10 Very Good! (1,014 reviews)

Great room

Reviewed on Oct 7, 2026

Lyle Washington D.C.

Northwest

Save 100% on your flight

$457

per person

Nov 23 - Nov 28

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.4/10 Exceptional! (1,645 reviews)

Overall it was fine, the staff specifically was very helpful and pleasant! My only issue was the water pressure for my room on the 7th floor was particularly bad, and the shower was even worse. Also, the AC units in the room are quite odd and don’t actually cool to the temperature you set them too. Otherwise it’s a great location.

Reviewed on Oct 6, 2026

Kellogg Conference Hotel at Gallaudet University

Northeast

Save 100% on your flight

$359

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.4/10 Very Good! (1,011 reviews)

Phoenix Park Hotel

Northwest

Save 100% on your flight

$451

per person

Nov 11 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.4/10 Exceptional! (2,166 reviews)

Nice classic old hotel and very clean and well maintained. We enjoyed our stay and will definitely book again.

Reviewed on Oct 6, 2026

Hyatt Regency Washington on Capitol Hill

Northwest

Save 100% on your flight

$362

per person

Nov 22 - Nov 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.8/10 Excellent! (1,012 reviews)

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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

2 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.

A Ferris wheel, a carousel, and a food stall at a fair.

Midtown Ocean City

2 out of top 10 points of interest in this area

Relax on golden sands, dabble in watersports, enjoy family-friendly amusements and play mini golf at this attractive coastal suburb.

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.

A marina with multiple sailboats docked.

West Ocean City

Discover fishing charters, boating, and marinas in this census-designated area, located across the Sinepuxent Bay from Ocean City. Shop at Outlets Ocean City and easily access the beach resort town via the Harry W. Kelley Memorial Bridge.

A group of horses grazing on a sandy beach with sparse vegetation.

Montego Bay

If you're spending some time in Montego Bay, Northside Park and Assawoman Bay are top sights worth seeing.

Stay near popular Eastern Shore attractions

A boardwalk entrance with a sign reading "Boardwalk Maryland" and two lighthouse-style structures.

Ocean City Boardwalk

9.0/10 (11,302 reviews)

This historic three-mile boardwalk has delighted visitors with ocean views and carnival charm since 1902. Savor local favorites like Thrasher's French Fries while exploring vintage amusement rides at Trimper's.

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A coastal cityscape with a sandy beach, ocean waves, and high-rise buildings.

Ocean City Beach

9.2/10 (10,973 reviews)

This classic 10-mile stretch of Atlantic shoreline pairs pristine sand with a vibrant, attraction-filled boardwalk. Enjoy free beach access year-round, with seasonal festivals adding extra charm to your coastal getaway.

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Roland E. Powell Convention Center

8.0/10 (2,358 reviews)

This modern bayfront venue hosts Ocean City's premier events, from trade shows to concerts. Enjoy panoramic water views while attending diverse exhibitions in its state-of-the-art facilities.

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A wooden boardwalk by a body of water with binoculars and a bench.

Inlet Park

8.6/10 (1,457 reviews)

Gaze across the Atlantic toward Assateague Island from this peaceful coastal viewpoint. The park's wooden "Whispering Giant" sculpture honors Native American heritage while offering wildlife spotting.

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A carousel, a large statue, and a building with a neon sign.

Jolly Roger Amusement Park

8.2/10 (3,806 reviews)

This dual-location amusement park features ocean-view rides at the Pier and thrilling water attractions at 30th Street. Enjoy illuminated attractions and panoramic Atlantic views from the Giant Wheel.

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A vibrant amusement park with a Ferris wheel, a prize factory, and various rides and attractions.

Jolly Roger at the Pier

8.4/10 (2,874 reviews)

This lively boardwalk amusement park dazzles with iconic rides like the Giant Wheel and Looping Star Roller Coaster. Evening visits offer magical views when colorful lights illuminate against the Atlantic sky.

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Salisbury University

8.4/10 (452 reviews)

Salisbury University's picturesque campus blends historic and modern architecture. Explore the Patricia R. Guerrieri Academic Commons for panoramic views and check the event calendar for cultural performances.

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Eastern Shore Hotel Deals

Castle in the Sand

3701 Atlantic Avenue Ocean City MD

$71 nightly

$80 total

Oct 11 - Oct 12

Total with taxes and fees

8.8/10 Excellent! (1,001 reviews)

"I would actually call this theft by deception! Absolutely nothing like the pictures. The whole establishment is beyond dirty. The only reason we stayed is because we had planned to be here for a country festival in an extra few days for our wedding anniversary. Worst pic ever has to be the dirtiest ..."

Reviewed on Oct 6, 2026

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD

$64 nightly

$72 total

Nov 1 - Nov 2

Total with taxes and fees

9/10 Wonderful! (3,947 reviews)

"The property was well maintained and the amenities were convenient and made the stay go very well."

Reviewed on Oct 6, 2026

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD

$100 nightly

$110 total

Nov 1 - Nov 2

Total with taxes and fees

See all 7,682 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.

Find the Best Eastern Shore Vacation Packages

Things to do near Eastern Shore

The Eastern Shore of Maryland offers a fantastic getaway for outdoor enthusiasts and beach lovers. Visitors can enjoy popular activities like exploring the boardwalk, relaxing in recreational areas, and taking in the beautiful scenery. Don't miss friendly attractions, waterfront tours, and opportunities to observe coastal wildlife. Customized and bus tours are also available to enhance your experience and help you discover the unique charm of this picturesque region.

Shopping

For a great shopping experience on the Eastern Shore, visit Queenstown Premium Outlets, located 15 miles away, offering a variety of stores and family-friendly vibes. Also, check out Bay Country Shop, 16 miles away, and the Bay Bridge Market Place Shopping Center, 26 miles away, for more shopping options.

Recreation

Experience the magic of Avalon Theatre, just a mile away, where culture and entertainment blend beautifully. For relaxation, head to Talbot Massage, located only 0.6 miles away, offering soothing treatments. If you're into sports, enjoy a round of golf at Queenstown Harbor Golf Links, 15 miles from Eastern Shore.

Adventure

Experience the thrill of sailing at Annapolis Sailing School, located 26 miles from Eastern Shore, where adventure meets water sports. Explore the picturesque St Michaels Nature Trail, 9 miles away, offering serene outdoor vibes. For tennis enthusiasts, Tose Family Tennis Center, also 26 miles away, provides an exciting atmosphere for competitive play.

Nightlife

The nightlife on the Eastern Shore is vibrant and diverse. Visit the Green Turtle for a fun atmosphere with games and great food. For a more laid-back vibe, check out the Crab Claw Restaurant, where you can enjoy waterfront views and live music on weekends.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Eastern Shore

Discover the beauty of Eastern Shore, Maryland, perfect for outdoor enthusiasts and beach lovers alike. Explore national parks, marinas, and history museums that offer rich cultural experiences and family-friendly activities. Don't miss the coastal charms that make this region unique, providing a perfect backdrop for relaxation and adventure during your vacation.

Talbot County Visitor Center: Located a mile from Eastern Shore, this visitor center offers a wealth of information about local attractions and outdoor adventures. Enjoy family-friendly activities and explore the natural beauty of the area, making it a great starting point for your adventures.
Academy of the Arts: Also a mile away, this art museum showcases the vibrant culture of the Eastern Shore. It features a variety of exhibits that celebrate local artists and art forms, providing an enriching experience for art enthusiasts and casual visitors alike.
The Third Haven Friends Meeting House: Situated two miles from Eastern Shore, this historic site is a serene and contemplative space. It offers a glimpse into the Quaker heritage of the region, blending culture and history in a tranquil setting.

Best time to go to Eastern Shore

The best time to visit Eastern Shore is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	34.2°F (1.2000000000000002°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Average	Average
April	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Average	Average
May	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average	Average
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	78.3°F (25.700000000000003°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	77.7°F (25.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	70.9°F (21.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	50.9°F (10.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
December	39.9°F (4.4°C)	Light Rain	Mostly Sunny	Slightly Low	Average

Tips to save on your trip to Eastern Shore

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Eastern Shore.
Consider traveling to Eastern Shore during the low season (January to February and November) for more affordable options.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.