Name: Waterside Inn
Price range: $206 total
Rating: 9

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

Save 100% on your flight

$639

per person

Jul 18 - Jul 21

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9.2/10 Wonderful! (1,901 reviews)

Great stay, all was excellent except breakfast.

Reviewed on Jun 7, 2026

Sea Ranch Resort

Save 100% on your flight

$837

per person

Aug 14 - Aug 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

8.6/10 Excellent! (1,004 reviews)

The room was amazing with a front view of the ocean

Reviewed on Jun 8, 2026

Chincoteague Bay RV Resort & Cottages

Save 100% on your flight

$822

per person

Aug 15 - Aug 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

10/10 Exceptional! (1 review)

Just one issue, I had to use our own blanket, bedsheets, and pillowcase because there was so much hair. So, I’m not sure if they changed them. But overall, it was a great vacation.

Reviewed on May 20, 2026

Fenwick Shores, Tapestry Collection by Hilton

$2,042

per person

Aug 30 - Sep 4

found 1 day ago

Roundtrip non-stop flight included

New York (LGA) to Salisbury (SBY)

9.6/10 Exceptional! (764 reviews)

Paying 16 dollars to park in the parking lot

Reviewed on Jun 7, 2026

Hilton Norfolk The Main

Downtown Norfolk

Save 100% on your flight

$1,144

per person

Aug 15 - Aug 22

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Norfolk (ORF)

9/10 Wonderful! (1,006 reviews)

Beautiful location and good customer service! Will definitely come back!

Reviewed on Jun 6, 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

Aerial view Fredericksburg Virginia with Circuit Court building , historic business district, Baptist church, Chatham bridge over Rappahannock River

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.

Discover the most popular places to visit in Eastern Shore of Virginia

Cape Charles Beach

Why not spend a carefree afternoon at Cape Charles Beach during your travels in Cape Charles? Wander the parks or discover the sunsets in this relaxing area.

Kiptopeke State Park

You can take time to visit Kiptopeke State Park during your travels to Cape Charles. Wander the beautiful beaches in this relaxing area.

Sun Star Near Beacon at Assateague Lighthouse-Chincoteague NWR

Eastern Shore of Virginia National Wildlife Refuge

Explore the great outdoors at Eastern Shore of Virginia National Wildlife Refuge, a lovely green space in Cape Charles. Wander the beautiful beaches in this relaxing area.

Eastern Shore of Virginia Hotel Deals

Key West Cottages

4251 Main Street Chincoteague VA

$300 nightly

$337 total

Jun 29 - Jun 30

Total with taxes and fees

9.8/10 Exceptional! (575 reviews)

"The property was gorgeous- cottage was perfect. We booked one of the 1 bedroom cottages. It had a small cooktop, microwave, fridge, freezer, dishwasher and kitchen supplies. Comfortable living room area. Bedroom and bathroom were both comfortable and beautifully decorated. Lovely front porch to watch ..."

Reviewed on Jun 7, 2026

Blufin Bungalows & Marina

2477 Main St Chincoteague VA

$240 nightly

$270 total

Jun 15 - Jun 16

Total with taxes and fees

9.6/10 Exceptional! (264 reviews)

"Wonderful stay with beautiful views or on water bungalow had all we needed and more"

Reviewed on Jun 9, 2026

Waterside Inn

3761 Main St Chincoteague VA

$183 nightly

$206 total

Jun 14 - Jun 15

Total with taxes and fees

9/10 Wonderful! (1,005 reviews)

"Simplicity at its best. The rooms were clean the view spectacular. The staff was very nice and helpful and friendly everyone wore a smile and seemed like they enjoyed their life! And the young lady serving breakfast in the morning. Was a sweetheart and very kind and friendly. I'm going back!"

Reviewed on Jun 8, 2026

See all 1,179 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.