Name: Key West Cottages
Price range: $237 total

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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

$682

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.2/10 Wonderful! (1,955 reviews)

The Historic Cavalier Hotel and Beach Club, Autograph Collection

Northeast Virginia Beach

$1,567

per person

Dec 28 - Jan 2

found 11 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.4/10 Exceptional! (410 reviews)

The Inn at Four Eleven York

West Freemason

$1,158

per person

Dec 28 - Jan 2

found 13 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

10/10 Exceptional! (114 reviews)

We stayed for our honeymoon before embarking on our cruise to Bermuda out of Norfolk. The port was very close to the Inn. The Inn is beautiful and so romantic. The area around the Inn had several options for dining. The walkable area was so romantic with its old architecture and cobblestone streets. I would love to come and stay longer and experience their restaurants and the city of Norfolk. I would highly recommend the Inn to anyone wanting a place that is not a big box type hotel. If you want charm and romance this place is for you!!!!

Reviewed on Oct 20, 2026

Sea Ranch Resort

$707

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

8.4/10 Very Good! (1,005 reviews)

Ocean Pines Resort

$818

per person

Dec 28 - Jan 2

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

8.2/10 Very Good! (162 reviews)

Perfect location and enjoyable stay

Reviewed on Oct 11, 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.

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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Eastern Shore of Virginia Hotel Deals

Waterside Inn

3761 Main St Chincoteague VA

$56 nightly

$63 total

Nov 1 - Nov 2

Total with taxes and fees

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA

Fully refundableReserve now, pay when you stay

$79 nightly

$89 total

Oct 28 - Oct 29

Total with taxes and fees

Key West Cottages

4251 Main Street Chincoteague VA

$211 nightly

$237 total

Nov 25 - Nov 26

Total with taxes and fees

See all 1,181 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.