Chesapeake City County Holidays

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Your Chesapeake City County Holiday

Leave the planning to us with a Chesapeake City County holiday package. With everything organised before you leave home, the only thing left for you to do is relax and experience this destination's beauty and culture. Not sure where your first stop should be? Chesapeake is among the most popular cities to visit during a trip to Chesapeake City County. Expedia has hotels, flights and all your other travel needs to help you put together your very own customised Chesapeake City County holiday today.

Top destinations in Chesapeake City County

Colorful sunset over riverside resort in Cambridge Maryland USA
FlightsFlightsHotelsHotels

Chesapeake

Chesapeake

Top Chesapeake City County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Price was £1,500, price is now £1,299 per person
£1,299
per person
8 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Norfolk (ORF)
8.2/10 Very Good! (1,502 reviews)
Loved it will be back for sure

Reviewed on 22 May 2026

The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Price was £1,609, price is now £1,350 per person
£1,350
per person
8 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Norfolk (ORF)
7.6/10 Good! (1,511 reviews)
Is a good place to stay just for a night. Reasonable price for what you get for!

Reviewed on 17 May 2026

The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was £1,826, price is now £1,576 per person
£1,576
per person
8 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Norfolk (ORF)
10/10 Exceptional! (107 reviews)
The building and the staff were great! Such a cute property and a really nice room. Only downside was that it was pretty loud due to traffic noise outside (and an early morning party in the parking lot next door). But the staff and amenities were really top notch, and breakfast was very tasty both days!

Reviewed on 26 Apr 2026

Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
Northeast Virginia Beach
Price was £1,621, price is now £1,435 per person
£1,435
per person
8 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Norfolk (ORF)
8/10 Very Good! (1,359 reviews)
Staff excellent! Could use continental breakfast

Reviewed on 20 May 2026

Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was £1,594, price is now £1,420 per person
£1,420
per person
8 Aug - 13 Aug
found 1 day ago
Return direct flight included
London (LON) to Norfolk (ORF)
8.8/10 Excellent! (1,014 reviews)
I’m staying every trip! Perfect place

Reviewed on 23 May 2026

Chesapeake City County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Top Sights
Chesapeake City Park, Lake Drummond and Oak Grove Lake Park

Top hotels in Chesapeake City County

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is £92 per night from 7 Jun to 8 Jun
£92
7 Jun - 8 Jun
includes taxes & fees
8/10 Very Good! (1,051 reviews)
"The hotel was clean, but older and not updated. The Jacuzzi in the pool area was not functional, and the outlet in my bathroom was not functioning so no use of hairdryer or other electric small appliances. Of the three Wyndham properties I stayed in on my travels, this was the most expensive but ..."

Reviewed on 24 May 2026

Wingate by Wyndham Chesapeake
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is £82 per night from 25 May to 26 May
£82
25 May - 26 May
includes taxes & fees
7.8/10 Good! (1,828 reviews)
"Stayed in the Jr. Executive Suite and loved the additional space the room offered. There are few photos but the 2nd floor suite (there are only 2 but the 2nd floor is the one I stayed in) has 2 separate balconies, ocean view, party over patio area, view is basically dead center of hotel with panoramic ..."

Reviewed on 24 May 2026

Wyndham Virginia Beach Oceanfront
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is £172 per night from 31 May to 1 Jun
£172
31 May - 1 Jun
includes taxes & fees
9.4/10 Exceptional! (2,280 reviews)
"It was perfect , clean and beautifull"

Reviewed on 23 May 2026

Hyatt Place Virginia Beach / Oceanfront
See all 3,456 properties in Chesapeake City County
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.
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Frequently asked questions

How much does a Chesapeake City County travel package cost?
Browse and book everything in one place with our Chesapeake City County travel packages, which start from only £1,299. Choose the hotels and flights that suit your travel plans. Then, add on a couple of experiences or tours to cap off your unique escape.
If I'm not able to travel, can I cancel my Chesapeake City County travel package?
We get that life doesn't always go according to plan. If you've locked in a Chesapeake City County travel package and have to cancel or change it, we're here to help. We suggest checking out our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to cancel or amend your itinerary for free. If it's been more than 24 hours, your airline, hotel or car rental company may impose a fee.
How do I get a cheap travel package to Chesapeake City County?
One word: bundle. Hotels, rental cars and flights — combine whatever you need into a Chesapeake City County holiday package to save loads of cash. Score even better deals when you include extras such as sightseeing tours to your booking. But that's not the only good part. You have the freedom to customize your holiday your own way. We offer more than 550 partner airlines and 1,000,000 hotels throughout the world, so that everyone has an opportunity to travel and live out those holiday dreams.
Does Expedia offer Book Now, Pay Later Chesapeake City County holidays?
Expedia has teamed up with online lender Klarna to make your next trip a bit easier on the wallet. Paying in instalments means you can spread the costs of your dream holiday, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying small amounts each month sounds right for you, pick this option during the checkout process.
  • Pay in instalments holidays: If you'd prefer to pay off your getaway across multiple transactions, holidays paid in instalments might be the right option for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan with Klarna.

What are the top hotels in Chesapeake City County?
Chesapeake is one place that most travellers to Chesapeake City County put on their itinerary. For a memorable stay here, have a look at Holiday Inn Express Chesapeake - Norfolk, an IHG Hotel and Red Roof Inn Chesapeake Conference Centre.
How far in advance should I book my Chesapeake City County holiday?
While not all air carriers release ticket prices early, you can normally compare international fares on Expedia up to a year in advance. This is when you can score some fantastic bargains. If you're booking last minute, you may still be in luck. Low prices occasionally emerge a few weeks prior to departure.
What does an Expedia Chesapeake City County travel package include?
Expedia has everything you need to lock in Chesapeake City County trip, but what your package looks like is your choice. Select from a combination of rental cars, hotels and flights. In search of some experiences or tours to keep you on the move? Once you've made your booking, you can add them too. Whatever your style or budget, there's a travel package to match your needs.
What should I know before booking a Chesapeake City County travel package?
You can save big by combining your airfares, hotels and rental cars. Once you've made your booking, add on fun stuff like tours and activities. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Chesapeake City County Expedia travel package?
Most definitely. Expedia has more than 550 partner airlines to pick from across the world. With all that choice, finding the perfect carrier to take you to Chesapeake City County will be a cinch.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.