Eastern Shore Trips (flight + hotel)

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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
Beach at Assateague Island National Seashore in Maryland on a sunny spring day. Useful for backgrounds, negative space

Ocean Pines

You'll enjoy the beaches and live music in Ocean Pines. You might want to make time for a stop at Ocean Pines Golf and Country Club or River Run Golf Club.

Find hotels in Ocean Pines

Things to do near Eastern Shore

Shopping

For a delightful shopping experience on the Eastern Shore, visit Easton Cycle and Sport, just 966m away, or explore the charming Saint Michaels Village, situated 12.9km from Eastern Shore. If you're after bargains, the Queenstown Premium Outlets, 24.1km away, offers a fantastic selection for all the family.

Recreation

Experience the charm of Avalon Theatre, offering a delightful mix of romance and culture just 1.6km away. Enjoy the outdoor sports vibe at Hog Neck Golf Course, located three miles from Eastern Shore. For ultimate relaxation, indulge in soothing treatments at Talbot Massage, only 966m away.

Adventure

Explore the St Michaels Nature Trail, a scenic path 14.5km from Eastern Shore, perfect for hiking and enjoying the great outdoors. For water enthusiasts, the Annapolis Sailing School offers thrilling sailing experiences, located 41.8km away. Additionally, engage in exciting tennis matches at the Tose Family Tennis Center, also 41.8km away.

Nightlife

The Eastern Shore offers a vibrant nightlife with venues like the lively Sunset Grille, perfect for waterfront dining and cocktails. For a more laid-back vibe, visit the Greyhound Café, where you can enjoy local brews and live music, creating a welcoming atmosphere for everyone.

*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 captivating beauty of Eastern Shore, Maryland, perfect for outdoor enthusiasts and beach lovers alike. Explore urban parks, national state parks, and marinas, offering a delightful mix of family activities and cultural experiences. Embrace the region's coastal charms as you immerse yourself in its scenic landscapes and vibrant atmosphere, ensuring a memorable getaway in this lovely part of the United States.

  • Easton Rail Depot: A charming historic site, Easton Rail Depot offers a glimpse into the region's rich railway history. With its preserved architecture and cultural vibes, visitors can enjoy a leisurely stroll while appreciating the heritage of transportation in the area.
  • Academy of the Arts: This art museum showcases an impressive collection of local and regional artworks. It’s a cultural haven where art enthusiasts can immerse themselves in exhibitions, workshops, and events that celebrate creativity and artistic expression.
  • Talbot County Visitor Center: A hub for adventure, the Talbot County Visitor Center provides insights into outdoor activities and family-friendly attractions. Explore the beautiful landscapes, engage in local events, and discover the best of what the area has to offer.

Best time to go to Eastern Shore

The best time to visit Eastern Shore can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Eastern Shore falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature around Eastern Shore falls in January, 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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • 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.

Top hotels in Eastern Shore

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 P14,877 per night from Jun 17 to Jun 18
P14,877
P16,662 total
Jun 17 - Jun 18
includes taxes & fees
9/10 Wonderful! (3,656 reviews)
"My stay at the Grand Hotel Ocean City Oceanfront was a mix of pros and cons. On the positive side, the room was spacious and very clean, which I truly appreciated. However, the check-in experience was disappointing; the staff member who assisted me was unwelcoming and acted quite rudely, making me ..."

Reviewed on Jun 9, 2026

Grand Hotel Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
The price is P15,430 per night from Jun 17 to Jun 18
P15,430
P18,260 total
Jun 17 - Jun 18
includes taxes & fees
8.8/10 Excellent! (2,456 reviews)
"We had a nice stay. Room could have been cleaner but we had a nice time and the staff was very nice."

Reviewed on Jun 9, 2026

Princess Royale Oceanfront Resort
Howard Johnson by Wyndham Ocean City Oceanfront

Howard Johnson by Wyndham Ocean City Oceanfront

2 out of 5
2401 Atlantic Ave Ocean City MD
The price is P12,297 per night from Jun 15 to Jun 16
P12,297
P13,772 total
Jun 15 - Jun 16
includes taxes & fees
8.6/10 Excellent! (1,009 reviews)
"We loved our stay at the Howard Johnson! The room was perfect, pool was great, and staff was so accommodating!"

Reviewed on Jun 8, 2026

Howard Johnson by Wyndham Ocean City Oceanfront
See all 7,884 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.

Popular places to visit

Carousel Ice Skating Rink

Carousel Ice Skating Rink

Enjoy a trip to Carousel Ice Skating Rink and popular activities like golfing in Ocean City. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

Carousel Ice Skating Rink
Jolly Roger at the Pier

Jolly Roger at the Pier

The old classics get a new spin at this waterfront fun park, which has an exciting collection of wild rides, high-octane roller coasters and traditional amusements.

Jolly Roger at the Pier

Assateague Island Visitor Center

After visiting Assateague Island Visitor Center, make a plan to see the other sights and activities in Berlin. Wander the beaches and seaside while you're in the area.

Assateague Island Visitor Center

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.