Eastern Shore of Virginia Vacations from $238

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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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

Northeast Virginia Beach
$238
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (1,006 reviews)
The Capes Hotel

The Capes Hotel

Northeast Virginia Beach
$339
per person
Nov 13 - Nov 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (555 reviews)
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

Northwest
$649
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (543 reviews)
This was one of the best hotels I've ever stayed in. The guest services/concierge desk personnel were friendly and helpful. Unfortunately the information they have for the hours that the kitchen is in operation is wrong. The website for both Kascades lounge, and Crown Plaza list the hours for dinner service as being from 4-10pm. I arrived at Kascades Lounge at 9:15pm and I was told that the kitchen had already been closed for 15 minutes. The housekeeping staff need to.leave the thermostat for the rooms alone while a guest is checked in. When I initially got to the room, the thermostat was set for 62° but it couldn't register the temperature well because it was definitely colder than that in the room. I personally set the temperature at 72° so that the room would be more comfortable for me, after the 1st night, I did what I needed to do throughout the day and when I returned to the room, the thermostat had been set back to 62° and the towels had not been refilled, I had to call and ask if someone could be sent up with fresh towels. I left some soft and energy drinks in the mini fridge so they would be cold when I wanted then, when I got into the room before the 2nd night, the mini fridge was empty and the drinks were nowhere to be found.

Reviewed on Sep 26, 2026

Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

Northeast Virginia Beach
$641
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8/10 Very Good! (1,514 reviews)
The Historic Cavalier Hotel and Beach Club, Autograph Collection

The Historic Cavalier Hotel and Beach Club, Autograph Collection

Northeast Virginia Beach
$1,232
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (405 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.

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.

Default Image

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.
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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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

Waterside Inn

3761 Main St Chincoteague VA
$56 nightly
$63 total
Oct 18 - Oct 19
Total with taxes and fees
9/10 Wonderful! (1,002 reviews)
"have stayed here several times over the years and have always enjoyed our stay. the front desk people are always kind and helpful. the rooms are always clean the beds comfortable, and you have great views from the balcony. the problem is no ramp up to the office so if you have limited mobility such ..."

Reviewed on Sep 25, 2026

Waterside Inn
Chincoteague Inn

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
$79 nightly
$89 total
Oct 1 - Oct 2
Total with taxes and fees
Chincoteague Inn
Key West Cottages

Key West Cottages

4251 Main Street Chincoteague VA
$224 nightly
$252 total
Oct 18 - Oct 19
Total with taxes and fees
9.8/10 Exceptional! (648 reviews)
"This is a 10/10 stay. Beautiful cottages, amazing views. Location is pristine! Must book!"

Reviewed on Sep 26, 2026

Key West Cottages
See all 1,189 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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