Eastern Shore of Virginia Vacation Packages 2026 from $269

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.

Boardwalk Resort and Villas

Northeast Virginia Beach

Save 100% on your flight

$269

per person

Sep 29 - Oct 3

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.8/10 Excellent! (1,002 reviews)

Beautiful view, well kept property, extremely helpful reception personnel, easy access to beach, rood layout is exceptional.

Reviewed on Aug 23, 2026

Sea Ranch Resort

Save 100% on your flight

$453

per person

Oct 3 - Oct 10

found 24 hours ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.4/10 Very Good! (1,009 reviews)

The staff was very helpful and friendly. Our room was clean with an amazing view!

Reviewed on Aug 24, 2026

The Capes Hotel

Northeast Virginia Beach

Save 100% on your flight

$447

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.6/10 Excellent! (512 reviews)

Blackbeard's Lodge

Save 100% on your flight

$613

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.4/10 Very Good! (384 reviews)

Blackbeard's is an older hotel very conveniently located on the island. maintenance lacks. Ice maker broken, faucets are loose etc. The staff, Cynthia, was very helpful and responsive.

Reviewed on Aug 23, 2026

The Ocean Key Virginia Beach Resort

Northeast Virginia Beach

Save 100% on your flight

$330

per person

Sep 24 - Sep 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

7.6/10 Good! (1,601 reviews)

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Where to stay in Eastern Shore of Virginia

Find the best Eastern Shore of Virginia areas and neighborhoods for the activities you enjoy most. Learn more about Eastern Shore of Virginia

A town with historic buildings, a prominent church with a tall steeple, and a river in the background.

Historic Downtown Cape Charles

If you're spending some time in Historic Downtown Cape Charles, Cape Charles Beach and Central Park are top sights worth seeing.

A field of horses near a body of water with a crowd in the background.

Downtown Chincoteague

While visiting Downtown Chincoteague, you might make a stop by sights like Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.

Beautiful marshlands next the ocean full of life - Assateague, MD, USA

Piney Island

1 out of top 10 points of interest in this area

While visiting Piney Island, you might make a stop by sights like Maui Jack's Waterpark and Museum of Chincoteague.

Deep Hole

Deep Hole might not have many top sights, but Maui Jack's Waterpark and Captain Timothy Hill House are two attractions nearby that you can check out.

Snotty Ridge

While there might not be top attractions in Snotty Ridge, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Assateague Point.

Stay near popular Eastern Shore of Virginia attractions

A wooden boardwalk leading to a beach with a sandy shore and dunes.

Cape Charles Beach

9.2/10 (237 reviews)

This gentle Chesapeake Bay beach offers calm, shallow waters perfect for families with children. Enjoy spectacular sunsets from wooden viewing platforms before exploring Cape Charles' charming historic district shops.

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A weathered, rusted pier with multiple rusted bollards and a partially intact structure.

Kiptopeke State Park

8.8/10 (105 reviews)

Explore the unique concrete ship breakwaters that now serve as vibrant artificial reefs for marine life. Hike coastal trails or cast a line from the fishing pier while watching migratory birds along the Atlantic Flyway.

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A red and white lighthouse with a small adjacent building, surrounded by trees and a clear sky.

Assateague Lighthouse

9.2/10 (509 reviews)

Learn about the local history of Chincoteague when you take a trip to Assateague Lighthouse. While you're in the area, stroll along the beautiful beaches.

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Assateague Point

9.6/10 (685 reviews)

Commune with nature and explore the great outdoors at Assateague Point during your travels in Chincoteague. While you're in the area, stroll along the beautiful beaches.

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Oyster Farm Marina

Explore the waterfront in Cape Charles with a trip to Oyster Farm Marina. Wander the beautiful beaches in this relaxing area.

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Maui Jack's Waterpark

8.0/10 (82 reviews)

Splash into Hawaiian-themed fun at Maui Jack's Waterpark, featuring thrilling water slides and a relaxing lazy river. Reserve a private cabana for a premium family experience during your Chincoteague Island adventure.

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Bay Creek Golf Club

8.0/10 (45 reviews)

Two legendary golf courses designed by Palmer and Nicklaus showcase stunning Chesapeake Bay views. Enjoy meticulously maintained fairways while spotting coastal wildlife on this prestigious waterfront retreat.

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Barrier Islands Center

8.4/10 (28 reviews)

You can spend time studying the exhibits at Barrier Islands Center in Machipongo. While you're in the area, stroll along the beautiful beaches.

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Eastern Shore of Virginia Hotel Deals

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA

Fully refundableReserve now, pay when you stay

$109 nightly

$122 total

Sep 7 - Sep 8

Total with taxes and fees

Waterside Inn

3761 Main St Chincoteague VA

$99 nightly

$112 total

Sep 13 - Sep 14

Total with taxes and fees

9/10 Wonderful! (1,017 reviews)

"Thank you 😊"

Reviewed on Aug 23, 2026

Blufin Bungalows & Marina

2477 Main St Chincoteague VA

9.6/10 Exceptional! (314 reviews)

"Our family of four had a wonderful stay at the Bluefinn! WiFi could’ve been a little better but everything else was really awesome! The pool was clean, refreshing, and never too crowded. The bungalows were very clean and surprisingly roomy for their size! The beds were very comfortable-best sleep ..."

Reviewed on Aug 24, 2026

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See all 1,203 properties in Eastern Shore of Virginia

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.