Eastern Shore of Virginia Holidays
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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
Historic Downtown Cape Charles
While visiting Historic Downtown Cape Charles, you might make a stop by sights like Cape Charles Beach and Central Park.
Downtown Chincoteague
While visiting Downtown Chincoteague, you might make a stop by sights like Robert N. Reed Downtown Waterfront Park and Chincoteague Channel.
Piney Island
While visiting Piney Island, you might make a stop by sights like Maui Jack's Waterpark and Museum of Chincoteague.
Deep Hole
When in Deep Hole, you can plan a visit to Captain Timothy Hill House and Maui Jack's Waterpark, some noteworthy sights in the nearby area.
Kiptopeke
While visiting Kiptopeke, you might make a stop by sights like Kiptopeke State Park and Chesapeake Bay.
Top hotels in Eastern Shore of Virginia
Waterside Inn
3761 Main St Chincoteague VA
S$84
20 Oct - 21 Oct
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Not worth what I paid for a night ($131) First room they gave me smelled terrible, musty and moldy. Couch and bedding smelled of mildew, maybe it was the carpet too but I wasn't daring enough to smell it. I at first thought it was because the ac was on and the filter was bad, so I turned it off and ..."
Reviewed on 9 Oct, 2026
Chincoteague Inn
4417 Deep Hole Road Chincoteague VA
Fully refundableReserve now, pay when you stay
S$114
12 Oct - 13 Oct
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"The property is a clean budget hotel. The rooms are large and the bathroom recently remodel. Location is right in the middle of town. Good value for chincoteague"
Reviewed on 4 Oct, 2026
Key West Cottages
4251 Main Street Chincoteague VA
S$278
12 Oct - 13 Oct
includes taxes & fees
9.8/10 Exceptional! (656 reviews)
"Clean, quiet, and convenient."
Reviewed on 9 Oct, 2026
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
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.
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.
Photo by Edith Shields
Assateague Lighthouse
9.2/10 (509 reviews)
Learn about the local history of Chincoteague when you spend time at Assateague Lighthouse. While you're in the area, stroll along the beautiful beaches.
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.
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.
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.
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.
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.
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
