Eastern Shore of Virginia Vacations from $635

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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.
Sea Ranch Resort

Sea Ranch Resort

$635
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (1,000 reviews)
If I were to rate this property based solely on location, I would give it five stars since it sits directly on the beach. Most rooms have balconies and we enjoyed several amazing sunrises, and time on the beach. Two of the three front desk personnel could have been friendlier. The place itself needs maintenance and updating. They do have a small restaurant which is convenient. The service and food were average. They offer nightly entertainment at a small venue that is attached and looks relatively new. The location is also great. It is near several attractions and good restaurants. With some TLC this place can easily be a five star property.

Reviewed on Sep 6, 2026

Blackbeard's Lodge

Blackbeard's Lodge

$817
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (397 reviews)
Very nice comfortable place to stay. Staff is very friendly and helpful.

Reviewed on Sep 4, 2026

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

$772
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.2/10 Wonderful! (1,927 reviews)
We had a really nice stay at the John Yancey Inn overall! The property and our room were very clean—honestly, probably one of the cleanest places we’ve stayed. The breakfast was also great and had a good variety. We really appreciated having a mini fridge and microwave in the room, and the bathroom was HUGE, especially the shower! There were a few things that kept the stay from feeling like a luxury hotel experience, though. The bed was extremely firm and uncomfortable for us, and we both woke up with back pain during our stay. The pillows also weren’t very comfortable. These things are obviously subjective, but after a long day at the beach, having a comfortable bed makes a big difference. We also noticed that the left side of the TV remote wasn’t working, including the power button and the “1” button, which was a little inconvenient. The biggest downside for us was the beach access. Unlike the other hotels/inns around us, there wasn’t a walkway or path from the property to the beach. You had to walk up and down the dunes, which was surprisingly difficult and inconvenient, especially when carrying beach chairs and other things. We were actually the only property we noticed without a dedicated path to the beach. Overall, we really appreciated how clean the property was, the great breakfast, the huge bathroom/shower, and the convenience of having a fridge and microwave. With a more comfortable bed and pillows and easier beach access, this would have been a much better expe

Reviewed on Sep 6, 2026

Pony Island Inn

Pony Island Inn

$917
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (499 reviews)
Best place to stay in Ocracoke Island: clean, great staff and centrally located to all of the things going on in the island. This is our third time staying here and we plan to come back next year.

Reviewed on Sep 4, 2026

Shutters on the Banks

Shutters on the Banks

$641
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.2/10 Wonderful! (1,973 reviews)
Good

Reviewed on Sep 5, 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.

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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.

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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.
Photo by Edith Shields

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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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

Waterside Inn

3761 Main St Chincoteague VA
$98 nightly
$110 total
Sep 27 - Sep 28
Total with taxes and fees
9/10 Wonderful! (1,004 reviews)
"Our room was clean and the bed was very comfortable. Our view of the bay was amazing on the balcony, with beautiful sunsets. The room was nice and spacious just a little musty smelling and we had ants and fruitflies to deal with. I know that's common on the island. We bought ant spray and a plug ..."

Reviewed on Sep 5, 2026

Waterside Inn
Chincoteague Inn

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
Chincoteague Inn
Comfort Suites Chincoteague Island Bayfront Resort

Comfort Suites Chincoteague Island Bayfront Resort

4195 Main St Chincoteague VA
Fully refundable
$133 nightly
$150 total
Oct 5 - Oct 6
Total with taxes and fees
Comfort Suites Chincoteague Island Bayfront Resort
See all 1,202 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.

Find the Best Eastern Shore of Virginia Vacation Packages

Eastern Shore of Virginia Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)

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