Eastern Shore of Virginia Vacation Packages 2026 from $1,019

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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.

Beach Bum Inn

Downtown Ocean City

$1,019

per person

Oct 31 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

8.2/10 Very Good! (362 reviews)

Small but clean and super close to boardwalk!

Reviewed on Sep 28, 2026

Princess Royale Oceanfront Resort

North Ocean City

$1,104

per person

Oct 31 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

8.8/10 Excellent! (2,780 reviews)

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$1,098

per person

Oct 31 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

9/10 Wonderful! (3,908 reviews)

Miramar Condominiums

Downtown Ocean City

$1,286

per person

Oct 31 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

9.4/10 Exceptional! (34 reviews)

Hotel Monte Carlo Ocean City

Downtown Ocean City

$1,093

per person

Oct 31 - Nov 2

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

7.8/10 Good! (1,000 reviews)

I am incredibly disappointed with how this hotel handles emergencies and treats its customers. This past weekend, an intense Nor'easter hit Ocean City, causing severe coastal flooding, major road closures, and life-threatening beach hazards. The Ocean City Police Department explicitly warned travelers to stay off the flooded roads and avoid downtown entirely, and the Oceans Calling Festival was completely canceled due to the dangerous conditions. Despite local authorities declaring the area a hazard and urging people to stay away, this hotel refused to issue a refund simply because they chose to keep their doors open. Expecting families to risk their safety and drive into a flooded storm zone just to avoid losing their money is completely unacceptable. A reputable business should prioritize customer safety over profit during a documented weather emergency. I will never book with them again.

Reviewed on Sep 29, 2026

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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.

A coastal landscape with a clear blue sky, a calm sea, and a marshy area with water reflecting the sky.

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 Captain Timothy Hill House and Maui Jack's Waterpark are two attractions nearby that you can check out.

An aerial view of a coastal area with a long, narrow breakwater extending into the sea, a sandy beach, and a distant shoreline with sparse vegetation.

Kiptopeke

If you're spending some time in Kiptopeke, Kiptopeke State Park and Chesapeake Bay are top sights worth seeing.

Stay near popular Eastern Shore of Virginia attractions

A coastal town with a sandy beach, houses, and a lighthouse.

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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A tall red and white lighthouse with a black top, surrounded by trees and a small building.

Eastern Shore of Virginia National Wildlife Refuge

8.8/10 (69 reviews)

A critical stopover on the Atlantic Flyway, this refuge shelters over 400 bird species across diverse habitats. Witness the spectacular fall migration of songbirds and monarchs from trails and observation deck.

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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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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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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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Cape Charles Harbor

This historic maritime gateway offers spectacular Chesapeake Bay views and a vibrant waterfront atmosphere. Stroll the public pier at sunset, then explore the adjacent historic district with its charming local shops.

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