Eastern Shore of Virginia Holidays

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Our guide on 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

While visiting Historic Downtown Cape Charles, you might make a stop by sights like Cape Charles Beach and Central Park.

Find hotels in Historic Downtown Cape Charles

Eastern Shore of Virginia Holiday

Our pick of the best Eastern Shore of Virginia Hotel Deals

Waterside Inn

Waterside Inn

2 out of 5
3761 Main St Chincoteague VA
The price is NZ$110 per night from 12 Nov to 13 Nov
NZ$110
12 Nov - 13 Nov
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"No internet connection. Comfortable. Friendly hostess for breakfast."

Reviewed on 31 Oct 2026

Waterside Inn
Chincoteague Inn

Chincoteague Inn

2 out of 5
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
The price is NZ$168 per night from 2 Nov to 3 Nov
NZ$168
2 Nov - 3 Nov
includes taxes & fees
Chincoteague Inn
Key West Cottages

Key West Cottages

3 out of 5
4251 Main Street Chincoteague VA
The price is NZ$226 per night from 2 Dec to 3 Dec
NZ$226
2 Dec - 3 Dec
includes taxes & fees
9.8/10 Exceptional! (669 reviews)
"First time on the island and will definitely be back to Key West Cottages."

Reviewed on 31 Oct 2026

Key West Cottages
See all 1,180 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.

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.
See properties

Frequently asked questions

How much does an Eastern Shore of Virginia holiday package cost?
Be ready to book, because a trip to Eastern Shore of Virginia starts from an affordable . When you combine your flights, hotels and car rentals into a travel package, you'll walk away with the biggest deals.
How do I get a cheap travel package to Eastern Shore of Virginia?
One word: bundle. Hotels, rental cars and flights — combine whatever you need into an Eastern Shore of Virginia holiday package to save tons of cash. Score even more bargains when you include extras such as day tours to your booking. But that's not the only good part. You have the flexibility to tailor your trip your own way. We offer over 550 partner airlines and 1 000 000 properties globally, so that everyone has a chance to travel and fulfil those holiday fantasies.
What are the top hotels in Eastern Shore of Virginia?
Princess Royale Oceanfront Resort and Carousel Resort Hotel & Condominiums know how to make their guests feel welcome in Greenbackville. If your itinerary also includes Exmore, look up Holiday Inn Express and Suites Exmore, Eastern Shore, an IHG Hotel and Shore Stay Suites. Both are very popular with travellers.
How far in advance should I book my Eastern Shore of Virginia holiday?
Get rewarded with the widest variety and the lowest prices by booking your adventure to Eastern Shore of Virginia nice and early. Airlines typically advertise flights around a year in advance, so start locking things in ASAP. Having said that, Expedia is dedicated to providing you with the best deals around, so there's never a bad time to book your dream holiday!
What does an Expedia Eastern Shore of Virginia travel package include?
Flights, rental cars and hotels — we've got them well covered. With Expedia, you can create your Eastern Shore of Virginia package just the way you want. All you have to do is figure out just what you need. Once you've made your booking, you can add on fun things like activities and experiences. The more you bundle, the more you save!
What should I know before booking an Eastern Shore of Virginia travel package?
Tailor deals that fit your budget with an Expedia package. Airfares, hotels, rental cars — we're a one-stop shop for all of them. You'll save precious cash just by combining your bookings. Whether you're going on a winter adventure or sipping cocktails on a beach, your dream getaway is only a few clicks away.
Can I choose my airline with an Eastern Shore of Virginia Expedia holiday package?
With a holiday package, you're the boss. Whether you're hoping to fly to Eastern Shore of Virginia in economy or first class, simply select from the available airline options. Expedia has access to over 550 airline partners worldwide.
If I'm not able to travel, can I cancel my Eastern Shore of Virginia holiday package?
You can cancel your Eastern Shore of Virginia booking if your plans have changed. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. You may be able to change or cancel free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.