Eastern Shore Holidays

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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
Wild horses hanging out on the beach, Assateague Island, Worcester County, Maryland.

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 Isle of Wight Bay.

Find hotels in Ocean Pines

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 Rp1.472.951 per night from 10 May to 11 May
Rp1.472.951
Rp1.649.705 total
10 May - 11 May
includes taxes & fees
9/10 Wonderful! (3,527 reviews)
Hotel was very clean throughout my stay and the room was big

Reviewed on 3 May 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 Rp1.733.700 per night from 12 May to 13 May
Rp1.733.700
Rp1.941.744 total
12 May - 13 May
includes taxes & fees
9/10 Wonderful! (1,605 reviews)
Yes everything was amazing

Reviewed on 3 May 2026

Hyatt Place Ocean City / Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
Oceanfront on 91st Street Ocean City MD
8.8/10 Excellent! (2,413 reviews)
The property was in an ideal spot and did their thing for the mini vacation I had while attending a work conference!

Reviewed on 3 May 2026

Get rates
Princess Royale Oceanfront Resort
See all 6,541 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.

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 travellers to Eastern Shore during the COVID-19 outbreak?
With the continuation of COVID-19, travelling 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 holiday 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 favourite and get ready for your next fun holiday!
What months are the cheapest to book a flight to Eastern Shore?
The most cost-effective month to book a top deal to Eastern Shore is February, whereas the most expensive is December. Try to avoid this month if you'd like to save money.
Which airlines with flights to Eastern Shore employ COVID-19 cleanliness policies?
To minimize contact between travellers 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.

How long is a flight to Eastern Shore?
Whether or not you'll have time to watch your favourite TV series from start to finish depends on where you're taking off from. To make planning your trip a little easier, here are the average flight times for some well-known domestic routes to Eastern Shore:
  • Atlanta, GA Airport (ATL-Hartsfield-Jackson Atlanta Intl.) to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) - 1 hour and 48 minutes
  • Chicago, IL Airport (ORD-O'Hare Intl.) to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) - 1 hour and 56 minutes
  • Orlando, FL Airport (MCO-Orlando Intl.) to Baltimore Washington Intl. Thurgood Marshall Airport (BWI) - 2 hours and 13 minutes

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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.