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Eastern Shore of Virginia Vacations from $428

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Your Eastern Shore of Virginia Vacation

With an Eastern Shore of Virginia vacation package, you can forget about the stress of planning and put all your energy into experiencing everything this thrilling destination has to offer. With so much to see and do on a trip to Eastern Shore of Virginia, it can be tricky to know where to start. Kick off your journey in Exmore at Chatham Vineyards and Northampton Shopping Center — two leading attractions here. Another city worthy of a spot on your itinerary is Greenbackville. Be sure not to miss Chincoteague National Wildlife Refuge and Maui Jack's Waterpark. Expedia has flights, hotels and everything else you need to help you organize your own tailored Eastern Shore of Virginia vacation today.

The Latest Eastern Shore of Virginia Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 13 - Jan 16

    John Yancey Oceanfront Inn + Flight

    Kill Devil Hills
    3 nights
    2.0 star property
    9.2/10 - Wonderful (1,961 reviews)
    "Very clean rooms and friendly staff."
    Reviewed November 3, 2026
    Roundtrip • San Antonio (SAT) - Norfolk (ORF)
    SAT - ORF • 1 stop ORF - SAT • 1 stop
    $543
    $428
    per traveler
    found 1 day ago
    John Yancey Oceanfront Inn
  • Jan 14 - Jan 18

    Boardwalk Resort and Villas + Flight

    Northeast Virginia Beach
    4 nights
    3.0 star property
    8.8/10 - Excellent (1,006 reviews)
    Roundtrip • New York (NYC) - Norfolk (ORF)
    JFK - ORF • Nonstop ORF - JFK • Nonstop
    $549
    $441
    per traveler
    found 1 day ago
    Boardwalk Resort and Villas
  • Dec 10 - Dec 13

    The Sitio + Flight

    Northeast Virginia Beach
    3 nights
    4.0 star property
    9.4/10 - Exceptional (86 reviews)
    "Amazing stay"
    Reviewed November 4, 2026
    Roundtrip • New York (JFK) - Norfolk (ORF)
    JFK - ORF • Nonstop ORF - JFK • Nonstop
    $913
    $745
    per traveler
    found 1 day ago
    The Sitio
  • Jan 14 - Jan 18

    Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia + Flight

    Northeast Virginia Beach
    4 nights
    4.0 star property
    8.2/10 - Very good (1,451 reviews)
    Roundtrip • New York (NYC) - Norfolk (ORF)
    JFK - ORF • Nonstop ORF - LGA • Nonstop
    $662
    $542
    per traveler
    found 1 day ago
    Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
  • Dec 18 - Dec 21

    Fenwick Shores, Tapestry Collection by Hilton + Flight

    Fenwick Island
    3 nights
    3.5 star property
    9.4/10 - Exceptional (881 reviews)
    "Fantastic experience. Top rate hotel. One of the best we have ever visited."
    Reviewed November 3, 2026
    Roundtrip • New York (NYC) - Salisbury (SBY)
    LGA - PHL • 1 stop PHL - JFK • 1 stop
    $528
    $448
    per traveler
    found 5 hours ago
    Fenwick Shores, Tapestry Collection by Hilton

Discover the most popular places to visit in Eastern Shore of Virginia

Eastern Shore of Virginia Hotel Deals

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

What's included in an Eastern Shore of Virginia vacation package?

An Eastern Shore of Virginia vacation package in Chincoteague lets you combine flights, hotel stays, and rental cars. Flights typically arrive at Norfolk International Airport (ORF). Most hotels in Chincoteague also offer free breakfast.


Exactly what's included will vary by hotel and package, so it's worth reviewing the details before you confirm your booking.

How can I save money on a Eastern Shore of Virginia vacation package?

When you bundle, you can save up to 30%*. To save money on a Eastern Shore of Virginia package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.

Which destinations should I consider for an Eastern Shore of Virginia vacation?

For an Eastern Shore of Virginia vacation, your choice of base depends on your preferred travel style:

  • Chincoteague: This is the main base for travelers seeking family-friendly attractions, outdoor activities, and romantic getaways, offering the most lodging choices in the region.
  • Cape Charles: Ideal for those who appreciate scenic views and beach-focused outdoor activities, with a good selection of accommodations.
  • Onancock: A quieter option for a relaxed trip, known for its scenic beauty and outdoor pursuits.
  • Exmore: A convenient base for families and outdoor enthusiasts, providing access to scenic views and various activities.

Is Eastern Shore of Virginia better suited for a beach vacation or a cultural trip?

The Eastern Shore of Virginia is primarily an outdoor and nature destination, with a strong focus on beaches and scenic views, making it ideal for a beach vacation.


Many of its constituent cities, such as Chincoteague and Cape Charles, are known for their beaches and outdoor activities. You can enjoy the sands of Cape Charles Beach or explore the natural beauty around Assateague Point.


While the region excels in natural attractions, it also offers cultural insights. Travelers can visit places like the Barrier Islands Center or the Eastern Shore Railway Museum to learn about local history and heritage. Overall, an Eastern Shore of Virginia vacation is best for those seeking coastal relaxation and outdoor adventures, with cultural experiences as a rewarding addition.

Which airport should I use for an Eastern Shore of Virginia vacation?

For an Eastern Shore of Virginia vacation, you have a few airport options that serve the wider region. Ronald Reagan Washington National Airport (DCA) in Washington, DC, and Norfolk International Airport (ORF) in Norfolk, VA, are the primary gateways. Both offer onward travel to the Eastern Shore, typically by car.

What are the top things to do in the Eastern Shore of Virginia?

An Eastern Shore of Virginia vacation is often centered around Chincoteague, which offers a variety of outdoor activities and family-friendly attractions:


Browse and book things to do in the Eastern Shore of Virginia on Expedia.

Can I change or cancel my Eastern Shore of Virginia vacation package if my plans change?

Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.

Do One Key members get extra savings when booking Eastern Shore of Virginia vacation packages?

Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.

Does Expedia offer Book Now, Pay Later Eastern Shore of Virginia vacation packages?

Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Eastern Shore of Virginia vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.

How do I find last-minute vacation packages to Eastern Shore of Virginia?

To find last-minute vacation packages to Eastern Shore of Virginia, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.

How does free cancellation work on Eastern Shore of Virginia vacation packages?

Free cancellation on a Eastern Shore of Virginia vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.

Is it cheaper to book a Eastern Shore of Virginia vacation as a package or separately?

An Expedia vacation package could land you great savings when compared to arranging flights and hotels separately. Better still, you can tailor your Eastern Shore of Virginia getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.

Why should I book my Eastern Shore of Virginia vacation package with Expedia?

Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.