Eastern Shore of Virginia Vacation Packages 2026 from $156

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.

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$156

per person

Dec 4 - Dec 6

found 1 hour ago

Roundtrip flight included

Atlanta (ATL) to Salisbury (SBY)

9/10 Wonderful! (3,946 reviews)

John Yancey Oceanfront Inn

$213

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

9.2/10 Wonderful! (1,946 reviews)

Stay was awesome! Courteous staff and great experience! Totally recommend!

Reviewed on Oct 15, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Northeast Virginia Beach

$902

per person

Dec 26 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

8.2/10 Very Good! (1,425 reviews)

I booked this property pretty last minute to enjoy the oceanfront while I was in town for a family wedding. The property was clean and the front desk staff was very friendly. I didn’t use any of the amenities as I was off-site most of the days I was there. The oceanfront views are amazing, right on the boardwalk. The room was well stocked, had everything one could possibly need and then some whether you’re there for a night or a week. I won’t hesitate to stay here again should I need accommodations away from family.

Reviewed on Oct 12, 2026

The Sitio

Northeast Virginia Beach

$1,662

per person

Dec 26 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.6/10 Exceptional! (74 reviews)

My absolute favorite place to stay in Virginia Beach

Reviewed on Oct 13, 2026

Roanoke Island Inn

Historic Downtown Manteo

$411

per person

Dec 4 - Dec 6

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

10/10 Exceptional! (103 reviews)

Staff and owners were very welcoming. We accidentally left a few items, which they offered to mail to us. Our kids loved the koi pond.

Reviewed on Oct 11, 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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Eastern Shore of Virginia Hotel Deals

Waterside Inn

3761 Main St Chincoteague VA

$56 nightly

$63 total

Oct 21 - Oct 22

Total with taxes and fees

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA

Fully refundableReserve now, pay when you stay

$79 nightly

$89 total

Oct 18 - Oct 19

Total with taxes and fees

8.6/10 Excellent! (1,000 reviews)

"The room was semi clean and in a good spot but the bed linens were strange. The comforter felt like wax paper. The floors turned my socks black but the bathroom was clean. Our tub backed up with what smelled like sewage but they moved us right away. No carts to move all our luggage and food which ..."

Reviewed on Oct 12, 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! (659 reviews)

"The cottage was so cute and cozy. It had everything we needed plus more. Easy location that was quite and peaceful. The beds were very comfortable. This is a great place to get away and relax. The front desk employees were awesome!"

Reviewed on Oct 15, 2026

See all 1,189 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.