Eastern Shore of Virginia Vacation Packages 2026 from $666

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

$666

per person

Nov 23 - Nov 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

8.8/10 Excellent! (1,006 reviews)

Staff and clean room

Reviewed on Oct 3, 2026

Beach Walk

Downtown Ocean City

$2,251

per person

Nov 15 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

7.6/10 Good! (126 reviews)

Do not know if it was Expedia or the place but the initial booking was a mess… the girl was trying to be helpful and stated that she would refund our first night but have not received any communications…. If you want “economy” in ever since of the word… no extra pillows walls are thin you can hear everyone’s conversations…. However the location is awesome… very convenient for walking to the inlet…. There is no elevator so pack light and they are held together by plywood

Reviewed on Oct 4, 2026

OCHG Beachviews

Downtown Ocean City

$1,187

per person

Nov 15 - Nov 18

found 23 hours ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

9.4/10 Exceptional! (10 reviews)

Miramar Condominiums

Downtown Ocean City

$1,385

per person

Nov 15 - Nov 18

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

9.4/10 Exceptional! (34 reviews)

The Colony at Virginia Beach

Northeast Virginia Beach

$983

per person

Nov 23 - Nov 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

9.2/10 Wonderful! (52 reviews)

Everything was clean and organized

Reviewed on Oct 4, 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 18 - Oct 19

Total with taxes and fees

9/10 Wonderful! (1,005 reviews)

"During the NorEaster that hit our stay was amazing! From the comfort of the room to the food that we enjoyed! Will definitely be back."

Reviewed on Oct 4, 2026

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA

Fully refundableReserve now, pay when you stay

$79 nightly

$89 total

Oct 11 - Oct 12

Total with taxes and fees

8.6/10 Excellent! (1,006 reviews)

"The property is a clean budget hotel. The rooms are large and the bathroom recently remodel. Location is right in the middle of town. Good value for chincoteague"

Reviewed on Oct 4, 2026

Key West Cottages

4251 Main Street Chincoteague VA

$215 nightly

$242 total

Oct 6 - Oct 7

Total with taxes and fees

9.8/10 Exceptional! (651 reviews)

"Perfect place for a weekend getaway or a week with family."

Reviewed on Oct 4, 2026

See all 1,186 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.