Eastern Shore of Virginia Vacation Packages 2026 from $189

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

$189

per person

Oct 30 - Nov 1

found 8 hours ago

Roundtrip flight included

Chicago (CHI) to Salisbury (SBY)

9/10 Wonderful! (3,884 reviews)

The Inn at Four Eleven York

West Freemason

$1,208

per person

Nov 23 - Nov 29

found 1 day ago

Roundtrip flight included

Chicago (MDW) to Norfolk (ORF)

10/10 Exceptional! (113 reviews)

Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away

$1,364

per person

Nov 24 - Nov 29

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

No reviews

Ocean View Inn

Cottage Line

$1,443

per person

Nov 23 - Nov 29

found 1 day ago

Roundtrip flight included

Chicago (MDW) to Norfolk (ORF)

6.2/10 (972 reviews)

Cloth cushions on very old chairs were badly stained. The room smelled old and moldy and there is mold in the shower. Pictures on the web must be 30 years old, as are the bedspreads, pillows, pillowcases, which were thin like crepe paper. No phone in the room. Wi Fi DID NOT WORK. This is a Bait And Switch, the room is not anything like the Web describes. We would not stay in a room that bad, and the old man at the desk just said "Call the third party" NO HELP. We deserve a full refund, but we're being told that we won't get that, losing 75% of our money.

Reviewed on Sep 11, 2026

Bethany Beach Ocean Suites Residence Inn by Marriott

Downtown Bethany Beach

$542

per person

Oct 16 - Oct 18

found 10 hours ago

Roundtrip flight included

Boston (BOS) to Salisbury (SBY)

9/10 Wonderful! (857 reviews)

The staff there were exceptional. The breakfast was excellent and the food was replenished regularly. Our only complaint was the mattress. Both my husband and I were extremely uncomfortable and had trouble sleeping.

Reviewed on Sep 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 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

$63 nightly

$70 total

Oct 12 - Oct 13

Total with taxes and fees

9/10 Wonderful! (1,002 reviews)

"Wonderful view and location. Nice pool."

Reviewed on Sep 11, 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! (1,001 reviews)

"I love to stay here because they have a huge outdoor kitchen that all guests are free to use. I hate being on the third floor and having to walk up and down the stairs."

Reviewed on Sep 8, 2026

Comfort Suites Chincoteague Island Bayfront Resort

4195 Main St Chincoteague VA

Fully refundable

$132 nightly

$149 total

Oct 12 - Oct 13

Total with taxes and fees

9.6/10 Exceptional! (1,002 reviews)

"Large clean room with excellent view. Comfortable bed. Walking distance to several restaurants. Would stay again"

Reviewed on Sep 10, 2026

See all 1,193 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.