Eastern Shore Vacations from ￥356,118

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The Latest Eastern Shore Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

Downtown Washington D.C.
￥356,118
per person
Nov 13 - Nov 18
found 14 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Baltimore (BWI)
9/10 Wonderful! (2,044 reviews)
This hotels delivers consistently good value. Beds are comfortable (not soft), bathrooms are clean and water is hot, and coffee maker in room is great, plus lounge on 2nd floor. Good location also. Suggest requesting a higher floor as neighborhood can get noisy.

Reviewed on Sep 29, 2026

Arlo Washington DC

Arlo Washington DC

Northwest
￥383,366
per person
Nov 13 - Nov 18
found 14 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Baltimore (BWI)
9.4/10 Exceptional! (2,000 reviews)
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

Downtown Washington D.C.
￥379,671
per person
Nov 13 - Nov 18
found 14 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Baltimore (BWI)
9/10 Wonderful! (1,249 reviews)
Hyatt Regency Washington on Capitol Hill

Hyatt Regency Washington on Capitol Hill

Northwest
￥422,821
per person
Nov 13 - Nov 18
found 14 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Baltimore (BWI)
8.8/10 Excellent! (1,004 reviews)
Holiday Inn Express Washington DC Downtown by IHG

Holiday Inn Express Washington DC Downtown by IHG

Downtown Washington D.C.
￥377,593
per person
Nov 13 - Nov 18
found 14 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Baltimore (BWI)
8.4/10 Very Good! (1,842 reviews)
Muy limpio y cómodo una excelente vista!!! Y el estacionamiento de buen tamaño para nuestra GMC yukon!! Volveríamos en un próximo viaje.

Reviewed on Sep 29, 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

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.

Find hotels in Downtown Ocean City
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

Midtown Ocean City is beloved for its stunning beaches. Take some time to explore sights in the area like Ocean City Beach and Seacrets Distilling Company.

Find hotels in Midtown Ocean City
A beach with a clear sky and calm sea.

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
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.

Find hotels in West Ocean City
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.

Find hotels in Montego Bay

Find the Best Eastern Shore Vacation Packages

Things to do near Eastern Shore

Shopping

Your shopping experience on the Eastern Shore will be delightful. Visit Easton Cycle and Sport for sports gear, explore the family-friendly Saint Michaels Village for unique gifts, and enjoy the Queenstown Premium Outlets for a mix of great deals and entertainment options, all within a short drive from Eastern Shore.

Recreation

Experience the charm of Avalon Theatre, just 1.6km away, where you can enjoy captivating performances in a romantic and cultural setting. For outdoor enthusiasts, Hog Neck Golf Course, 4.8km away, offers a scenic golfing experience. For ultimate relaxation, visit Talbot Massage, located only 966m away, to enjoy soothing body treatments.

Adventure

St. Michaels Nature Trail offers a scenic adventure with outdoor vibes, perfect for hiking and enjoying nature, located 14.5km from Eastern Shore. For water sports enthusiasts, the Annapolis Sailing School provides thrilling sailing experiences, 41.8km away, while the Tose Family Tennis Center offers exciting tennis activities, also 41.8km away.

Nightlife

The nightlife in Eastern Shore offers a mix of vibrant bars and cozy spots. For live music and craft cocktails, visit The Avalon Theatre, or enjoy a laid-back evening at The Greene Turtle for good food and drinks. Don't miss the lively atmosphere at the Ocean City Boardwalk.

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

Find the best attractions near Eastern Shore

Eastern Shore, Maryland, is an ideal destination for outdoor enthusiasts and families seeking scenic beach experiences. Visitors can explore urban parks, state parks, and marinas, all while enjoying the region's coastal charms. Whether you're interested in outdoor activities, cultural experiences, or simply relaxing in nature, Eastern Shore offers a variety of attractions that cater to every traveler’s needs.

  • Academy of the Arts: Immerse yourself in the vibrant culture at the Academy of the Arts, an art museum that showcases a diverse collection of local and regional artworks. Located just 1.6km from Eastern Shore, it offers a unique opportunity to appreciate the creativity and talent of the community.
  • Talbot County Visitor Center: Adventure awaits at the Talbot County Visitor Center, also 1.6km away. This center is perfect for families, featuring outdoor activities and resources to help you explore the stunning natural beauty of the Eastern Shore region.
  • The Third Haven Friends Meeting House: Step back in time at The Third Haven Friends Meeting House, a historic site located 3.2km from Eastern Shore. With its charming architecture and serene atmosphere, it provides a glimpse into the region's rich cultural heritage.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January34.2°F (1.2000000000000002°C)Light RainMostly SunnySlightly LowSlightly Low
February36.9°F (2.7°C)Light RainMostly SunnySlightly LowSlightly Low
March43.7°F (6.5°C)Light RainMostly SunnyAverageAverage
April54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
May63.7°F (17.6°C)Light RainMostly SunnyAverageAverage
June72.1°F (22.3°C)Light RainMostly SunnySlightly HighSlightly High
July78.3°F (25.700000000000003°C)Light RainMostly SunnySlightly HighAverage
August77.7°F (25.4°C)Light RainMostly SunnySlightly HighAverage
September70.9°F (21.6°C)Light RainMostly SunnyAverageSlightly High
October59.2°F (15.1°C)Light RainMostly SunnyAverageSlightly High
November50.9°F (10.5°C)Light RainMostly SunnyAverageSlightly Low
December39.9°F (4.4°C)Light RainMostly SunnySlightly LowAverage

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 during the off-peak season (typically January to February and November) for more affordable package holidays to Eastern Shore.
  • 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.

Eastern Shore Hotel Deals

Fenwick Inn

Fenwick Inn

13801 Coastal Highway Ocean City MD
Fully refundableReserve now, pay when you stay
￥11,182
￥14,875 total
Oct 14 - Oct 15
includes taxes & fees
Fenwick Inn
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD
￥10,862
￥12,164 total
Oct 28 - Oct 29
includes taxes & fees
Grand Hotel Ocean City Oceanfront
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

4801 Coastal Highway Ocean City MD
Fully refundable
￥10,848
￥14,090 total
Oct 7 - Oct 8
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)
"The room we checked into was horrible. Clearly there had been water damage in the bathroom, and there was damage around the exterior window. The electrical was dated. There was some weird substance around the air conditioner unit, and what looked like painted over mold/mildew on the bathroom ceiling. ..."

Reviewed on Sep 28, 2026

Princess Bayside Beach Hotel
See all 7,765 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.

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.
See properties
A pier with people on it, a beach, and a roller coaster in the background.

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 stone wall with the text "Roland E. Powell Convention Center" and a landscaped area with trees and shrubs.

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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Frequently asked questions

How much does an Eastern Shore vacation package cost?
Get ready to book, because a getaway to Eastern Shore starts from an affordable ￥356,118. When you combine your hotels, flights and car rentals into a package, you'll pick up the biggest deals.
How do I get a cheap travel package to Eastern Shore?
It's as simple as bundling. Hotels, flights and rental cars — combine whatever you need into an Eastern Shore vacation package and save. Score even more discounts when you add extras such as sightseeing tours to your booking. But that's not the only good part. You have the freedom to tailor your vacation your way. We offer more than 550 airlines and 1,000,000 hotel options worldwide, so that everyone has a chance to travel and live out those vacation dreams.
What are the top hotels in Eastern Shore?
Wingate by Wyndham Baltimore BWI Airport and Renaissance Baltimore Harborplace Hotel know how to make their guests feel at home in Ocean City. If your travel plans also include Berlin, check out Fenwick Inn and Hilton Garden Inn Ocean City Oceanfront. Both are top picks with travelers.
How far in advance should I book my Eastern Shore vacation?
Savvy travelers often reserve their seats as early as possible. You can usually start comparing international airfares on Expedia up to a year before your intended flight. If you're late to book, don't worry. Bargain prices sometimes occur just weeks prior to departure.
What does an Expedia Eastern Shore travel package include?
It all comes down to what kind of getaway you're contemplating. Eastern Shore travel deals can include car rentals, hotels and flights. You can mix and match to create the package that suits your needs. You can also add on experiences and activities after you've booked to score even bigger discounts.
What should I know before booking an Eastern Shore travel package?
A travel package can be tailored to your budget and is a great way to make your hard-earned dollars stretch further. How much you include is your call. Rental cars, hotels and flights — choose any combination that suits your style.
Can I choose my airline with an Eastern Shore Expedia vacation package?
With a vacation package, you're the boss. Whether you're eager to fly to Eastern Shore in first class or coach, simply choose from the available airline options. Expedia has access to over 550 partner airlines across the world.
If I'm not able to travel, can I cancel my Eastern Shore vacation package?
Yes, you can. We understand that things don't always go to plan, so we're here to help if you have to make changes to your Eastern Shore vacation package. It may be possible to cancel or amend your itinerary for free if you've booked in the last 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.

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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.