Name: Key West Cottages
Price range: $383 total
Rating: 9.8

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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

$405

per person

Oct 2 - Oct 5

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

8.6/10 Excellent! (1,003 reviews)

Great beach access; food at onsite restaurant was good; bed was totally uncomfortable and did not sleep well, and room smelled super musty/moldy.

Reviewed on Jul 11, 2026

The Colony at Virginia Beach

Northeast Virginia Beach

Save 100% on your flight

$768

per person

Aug 11 - Aug 15

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

9.4/10 Exceptional! (23 reviews)

Property was clean, and staff friendly.

Reviewed on Jul 6, 2026

The Burrus House Inn Waterfront Suites

Save 100% on your flight

$705

per person

Oct 2 - Oct 5

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.8/10 Exceptional! (31 reviews)

Lovely property on the water. Suites are spacious with wet bar/frig/microwave.

Reviewed on Jul 11, 2026

Ambassadors Inn & Suites

Northeast Virginia Beach

Save 100% on your flight

$1,576

per person

Sep 22 - Sep 26

found 19 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Norfolk (ORF)

6/10 (1,005 reviews)

clean room, and staff was very helpful

Reviewed on Jul 10, 2026

John Yancey Oceanfront Inn

$474

per person

Oct 2 - Oct 5

found 21 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.2/10 Wonderful! (1,912 reviews)

Great location, nice staff, good breakfast. Room included a refrigerator, microwave, stove, and even cooking utensils!

Reviewed on Jul 10, 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 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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Eastern Shore of Virginia Hotel Deals

Chincoteague Inn

4417 Deep Hole Road Chincoteague VA

Fully refundableReserve now, pay when you stay

$128 nightly

$144 total

Jul 26 - Jul 27

Total with taxes and fees

8.4/10 Very Good! (1,007 reviews)

"Very clean room, staff was nice and definitely great air conditioning!!!"

Reviewed on Jul 10, 2026

Blufin Bungalows & Marina

2477 Main St Chincoteague VA

$391 nightly

$439 total

Jul 12 - Jul 13

Total with taxes and fees

9.6/10 Exceptional! (285 reviews)

"Overall a good stay, a few hiccups at check-in but we would return."

Reviewed on Jul 10, 2026

Key West Cottages

4251 Main Street Chincoteague VA

$341 nightly

$383 total

Aug 4 - Aug 5

Total with taxes and fees

9.8/10 Exceptional! (595 reviews)

"Loved the pool! View on bay was beautiful! Cottages are cute!"

Reviewed on Jul 10, 2026

See all 1,194 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.