Eastern Shore of Virginia Vacation Packages 2026 from $402

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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

$402

per person

Sep 15 - Sep 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

9.2/10 Wonderful! (1,921 reviews)

White Marlin Inn

Downtown Ocean City

$1,076

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

5.4/10 (45 reviews)

I want to share that location is great because you’re only one block away from the boardwalk. On the other hand, the room was in poor condition. The AC was full of dust and debris and the wall around it. The ceiling had several wet stains and the smell was bad. It appeared that the room had not been cleaned for a while. The cleaning ladies didn’t appear to be very motivated. I had to request broom, dust pan and toilet tissue. There’s no microwave to warm up food. The parking fee was not included so I had per that separate per day. The check in staff were very nice and friendly.

Reviewed on Aug 8, 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)

9.4/10 Exceptional! (176 reviews)

Sea Breeze Inn

Downtown Ocean City

$1,245

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

6.4/10 (55 reviews)

Great location. Overall the room was fine. Everything was in decent shape - carpet, furniture, bedding, paint, bathroom tiles, etc. Bedside lamp didn’t work. Toilet seat was the wrong size (long seat, round toilet). Some mold in the shower. AC unit was super loud but cooled the room well. Bathroom window would not crank closed at all (crank mechanism was broken). A lot of street/alley noise entered the room from the bathroom window and AC window. It’s a case of getting what you pay for. The room was as I expected for what I paid.

Reviewed on Aug 8, 2026

Stonewood Inn & Suites Carrollton - Smithfield

$471

per person

Sep 18 - Sep 25

just found

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)

5.6/10 (196 reviews)

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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.

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 Maui Jack's Waterpark and Captain Timothy Hill House 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.

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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 rustic wooden structure with a rusted roof by a body of water.

Oyster Bay

9.2/10 (121 reviews)

Oyster Bay offers a serene waterfront retreat on Chincoteague Island with picturesque views. Enjoy fishing from private docks or kayaking while watching for local wildlife in this peaceful coastal haven.

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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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Oyster Farm Marina

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

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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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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 7 - Sep 8

Total with taxes and fees

8.6/10 Excellent! (1,009 reviews)

"place was okay for a one night stop over in a popular summer resort area. Easy access to good restaurants, nice pool, room was very basic and could use a re-fresh - it was clean but simple. Probably gets a lot of traffic during summer months. Staff was nice."

Reviewed on Aug 8, 2026

Blufin Bungalows & Marina

2477 Main St Chincoteague VA

$359 nightly

$403 total

Aug 13 - Aug 14

Total with taxes and fees

Key West Cottages

4251 Main Street Chincoteague VA

$242 nightly

$272 total

Sep 8 - Sep 9

Total with taxes and fees

9.8/10 Exceptional! (610 reviews)

"Our second stay. Well laid out. Small but very comfortable. Great get away. Very good location. Easy walk. Easy bike ride. Short drive to sea shore."

Reviewed on Aug 7, 2026

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.