Eastern Shore Vacations from ¥137,061

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The Latest Eastern Shore Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Best Western Plus Laurel
DoubleTree by Hilton Hotel Laurel
Crowne Plaza College Park - Washington DC by IHG
Comfort Inn College Park North
Comfort Inn Laurel - Fort Meade

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

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

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
Fully refundable
The price is ¥14,321 per night from Feb 16 to Feb 17
¥14,321
¥18,333 total
Feb 16 - Feb 17
includes taxes & fees
8.6/10 Excellent! (2,328 reviews)
Staff was friendly and helpful room was spacious

Reviewed on Feb 3, 2026

Princess Royale Oceanfront Resort
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
9/10 Wonderful! (3,437 reviews)
The only place we stay when we go to Ocean City. Great location, plenty of parking, friendly staff, good food, 2 arcade areas! On the boardwalk, far enough from the inlet crowds, but a nice walk. Great beach location & views.

Reviewed on Feb 1, 2026

Grand Hotel Ocean City Oceanfront
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 ¥12,833 per night from Feb 19 to Feb 20
¥12,833
¥14,373 total
Feb 19 - Feb 20
includes taxes & fees
9/10 Wonderful! (1,576 reviews)
The staff were very courteous. The room was mostly clean (under the dresser was very dusty, and there was lots of trash), but otherwise the views were great, and the room was very comfortable. If I have the chance, I will return.

Reviewed on Feb 3, 2026

Hyatt Place Ocean City / Oceanfront
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.

Discover the most popular places to visit in Eastern Shore

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.