Eastern Shore of Virginia Vacation Packages 2026 from $258

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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.

Sandcastle Resort On The Beach

Northeast Virginia Beach

Save 100% on your flight

$258

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

7.8/10 Good! (1,032 reviews)

Todo estaba bien , recomendaría el hotel a otras personas !!!

Reviewed on Aug 10, 2026

Boardwalk Resort and Villas

Northeast Virginia Beach

Save 100% on your flight

$267

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.8/10 Excellent! (1,007 reviews)

This was our second stay at this resort and we love it. Hope to be back. The front desk crew is awesome!! They call and/or text checking on you and ur needs throughout your stay

Reviewed on Aug 10, 2026

Sea Ranch Resort

Save 100% on your flight

$457

per person

Sep 22 - Sep 29

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Norfolk (ORF)

8.4/10 Very Good! (1,009 reviews)

No phone or tv No help from front desk either The entire property needs an upgrade. Not worth the money.

Reviewed on Aug 11, 2026

Sea Scape Beach and Golf Villas

Sea Scape

Save 100% on your flight

$640

per person

Sep 19 - Sep 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

9.2/10 Wonderful! (177 reviews)

John Yancey Oceanfront Inn

$589

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

9.2/10 Wonderful! (1,920 reviews)

It was our first time staying there. The staff was very helpful, everytwas so clean and well-maintained.

Reviewed on Aug 10, 2026

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore of Virginia

View all trips

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.

Beautiful marshlands next the ocean full of life - Assateague, MD, USA

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.

Snotty Ridge

While there might not be top attractions in Snotty Ridge, you can explore the larger area and discover places like Robert N. Reed Downtown Waterfront Park and Assateague Point.

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

Oyster Farm Marina

Explore the waterfront in Cape Charles with a trip to Oyster Farm Marina. Wander the beautiful beaches in this relaxing area.

See properties

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.

See properties

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.

See properties

Eastern Shore of Virginia Hotel Deals

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA

Fully refundableReserve now, pay when you stay

$99 nightly

$111 total

Sep 8 - Sep 9

Total with taxes and fees

Blufin Bungalows & Marina

2477 Main St Chincoteague VA

$359 nightly

$403 total

Aug 20 - Aug 21

Total with taxes and fees

9.6/10 Exceptional! (306 reviews)

"We have never stayed in a cottage on the water before but we’d thought we’d try it. It wasn’t too bad you could feel some movement but nothing to get sick over. The rooms were very nicely decorated and comfortable. Pros: clean rooms, close to parking, pool etc., affordable, nice pool, close to the ..."

Reviewed on Aug 11, 2026

Waterside Inn

3761 Main St Chincoteague VA

$115 nightly

$129 total

Sep 7 - Sep 8

Total with taxes and fees

See all 1,200 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.