Eastern Shore of Virginia Vacation Packages 2026 from $254

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.

John Yancey Oceanfront Inn

Save 100% on your flight

$254

per person

Nov 9 - Nov 13

found 10 hours ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

9.2/10 Wonderful! (1,924 reviews)

The Sitio

Northeast Virginia Beach

Save 100% on your flight

$1,276

per person

Dec 4 - Dec 11

found 4 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.6/10 Exceptional! (61 reviews)

Beautiful property, friendly staff. Comfortable bed. Great stay! Will be back in the future as my son is military and he is stationed in Virginia Beach.

Reviewed on Sep 15, 2026

The Barclay Towers Resort Hotel

Northeast Virginia Beach

$660

per person

Dec 4 - Dec 11

found 4 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

8/10 Very Good! (1,015 reviews)

Some issues with the carpet being wet. Toilet didn't flush properly. Maintenance responded quickly for the carpet, but front desk didn't seem worried about the smell that remained and didn't offer to change our room. Coffee maker in lobby was broken and coffee supplies in the room weren't great. We were able to do a pre-check in so we could get a parking pass to be able to park in lot to go to the beach.

Reviewed on Sep 16, 2026

Boardwalk Resort and Villas

Northeast Virginia Beach

$790

per person

Nov 29 - Dec 6

found 18 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

8.8/10 Excellent! (1,006 reviews)

Very clean, convenient and affordable

Reviewed on Sep 17, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$316

per person

Oct 23 - Oct 26

found 9 hours ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.2/10 Very Good! (1,387 reviews)

It is a time share so they do not provide daily housekeeping. Clean linens are available in a hall closet

Reviewed on Sep 16, 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 Maui Jack's Waterpark and Captain Timothy Hill House 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 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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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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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

Waterside Inn

3761 Main St Chincoteague VA

$66 nightly

$74 total

Oct 18 - Oct 19

Total with taxes and fees

9/10 Wonderful! (1,001 reviews)

"While this property was surely not perfect, the total experience was. The rooms are dated, not very clean, functional and asky rooms have a beautiful water view with a little b balcony. Even the elevator has windows and a water view. The staff is very friendly and accommodating. the breakfast is ..."

Reviewed on Sep 16, 2026

Key West Cottages

4251 Main Street Chincoteague VA

$224 nightly

$252 total

Oct 18 - Oct 19

Total with taxes and fees

9.8/10 Exceptional! (639 reviews)

"This was the perfect relaxing get away! Clean and quiet! Already booked for next spring 2027!"

Reviewed on Sep 16, 2026

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA

Fully refundableReserve now, pay when you stay

$89 nightly

$100 total

Sep 27 - Sep 28

Total with taxes and fees

8.6/10 Excellent! (1,002 reviews)

"My second time staying here and it’s great! The staff are very helpful. Clean room and a great stay."

Reviewed on Sep 16, 2026

See all 1,192 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.