Eastern Shore Vacation Packages 2026 from $282

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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.

The Westin DC Downtown

Downtown Washington D.C.

Save 100% on your flight

$282

per person

Oct 9 - Oct 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.8/10 Excellent! (1,008 reviews)

Kellogg Conference Hotel at Gallaudet University

Northeast

Save 100% on your flight

$546

per person

Oct 9 - Oct 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

8.4/10 Very Good! (1,006 reviews)

I love that it’s located on university campus, great for family bringing students from out of state.

Reviewed on Aug 5, 2026

The River Inn

Northwest

Save 100% on your flight

$382

per person

Oct 9 - Oct 12

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9.4/10 Exceptional! (2,056 reviews)

Hotel Burg

Leesburg's Old and Historic District

Save 100% on your flight

$1,034

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Boston (BOS) to Baltimore (BWI)

9.6/10 Exceptional! (100 reviews)

Excellent service and hospitality. Beautiful and clean. Would come back here many times. Friendly and professional staff. It was a great experience.

Reviewed on Aug 4, 2026

Furnished Apartments

Ashton Heights

Save 100% on your flight

$745

per person

Sep 9 - Sep 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Baltimore (BWI)

9/10 Wonderful! (4 reviews)

Location is excellent. Walking distance to pretty much everything you need. Space was very comfortable, clean, and the bed was excellent for sleeping. Lots of light and windows. Host was helpful and able to accommodate my schedule needs too.

Reviewed on Apr 1, 2025

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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.

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 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.

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 coastal cityscape at dusk with illuminated buildings and a marina.

Sunset Island

While there might not be top attractions in Sunset Island, you can explore the larger area and discover places like Seacrets Distilling Company and Seacrets.

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

9.0/10 (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 wooden pier extending into the ocean with a person standing at the end.

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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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 wooden pier extending into calm waters, a modern building with large windows, and a clear blue sky.

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 swimming pool with people on inflatable rings, surrounded by a grassy area and teepees.

Frontier Town Water Park and Golf

9.0/10 (2 reviews)

This Western-themed water park combines thrilling slides and a lazy river with an Old West ambiance. Families can enjoy the 18-hole mini golf course with scenic waterfalls before cooling off in the splash pad.

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Eastern Shore Hotel Deals

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD

$151 nightly

$167 total

Sep 7 - Sep 8

Total with taxes and fees

8.8/10 Excellent! (2,623 reviews)

"The location on the beach was the best, easy walk. The indoor pool was nice but the temp in the pool needed to be higher because you couldn’t swim in it past 3 pm without it being freezing. The side corner balconies are very sketchy to sit on. The rooms themselves need a lot of maintenance done. ..."

Reviewed on Aug 8, 2026

Fenwick Inn

13801 Coastal Highway Ocean City MD

Fully refundableReserve now, pay when you stay

$102 nightly

$115 total

Sep 7 - Sep 8

Total with taxes and fees

8.8/10 Excellent! (2,071 reviews)

"Bringing my dogs was great. Breakfast was good too. My only complaint was that the floors were not clean well."

Reviewed on Aug 7, 2026

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD

Fully refundableReserve now, pay when you stay

$154 nightly

$172 total

Sep 7 - Sep 8

Total with taxes and fees

9/10 Wonderful! (3,749 reviews)

"I loved the conveniences of buying meals and souvenirs without traveling far."

Reviewed on Aug 8, 2026

See all 7,937 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.