Chesapeake Vacations

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Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Greenbrier Mall

Greenbrier East

4/5(438 area reviews)

While visiting Greenbrier East, you might make a stop by sights like Greenbrier Mall and Jillian's Billiards.

Find hotels in Greenbrier East

Find the Best Chesapeake Vacation Packages

Chesapeake Hotel Deals

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is ₩275,914 per night from Jun 29 to Jun 30
₩275,914
₩320,016 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
"Great stay! Will be coming again."

Reviewed on Jun 25, 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
3 out of 5
1801 Atlantic Ave, Virginia Beach, VA
Fully refundable
The price is ₩310,199 per night from Jul 2 to Jul 3
₩310,199
₩359,451 total
Jul 2 - Jul 3
includes taxes & fees
8.2/10 Very Good! (2,167 reviews)
Good hotel, but watch the price.
"Check-in was great. We arrived a little ahead of time and our room was ready, so we got in and hit the beach earlier than we thought for the day. Parking on-site was fine and included. Great beach proximity. Our room was on the first floor across from the elevator. People are loud and dumb at all ..."

Reviewed on Jun 25, 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Schooner Inn
Schooner Inn
2 out of 5
215 Atlantic Ave, Virginia Beach, VA
8.6/10 Excellent! (3,183 reviews)
"Very clean and great view"

Reviewed on Jun 24, 2025

Get rates
Schooner Inn
See all 3,395 properties in Chesapeake
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.

Frequently asked questions

How much does a Chesapeake vacation package cost?
You'll find cheap prices on Expedia for your Chesapeake escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Chesapeake costs.
What are the cheapest months to go to Chesapeake?
If you'd like to book a cheap Chesapeake vacation package, consider planning a trip in January, February and November. You'll generally find better prices on accommodations and flights during these months --- perfect for travelers wishing to save money.
How many days is enough for Chesapeake?
Chesapeake vacations can be as short or long as you like, but to get a real feel for this destination, we reckon 2 days is about right. With this timeframe, you can fit in top sights like Chesapeake City Park and Oak Grove Lake Park along with lesser-known spots. Don't forget to visit neighborhoods such as Greenbrier East and Greenbrier West either. If you're smart with your time, you can even take a day trip from Chesapeake too.
Is it worth booking a vacation package to Chesapeake?
Well known for its nature, adventure sports and hiking, a Chesapeake vacation has something for everyone. Be sure to check out major sights like Portlock Galleries at SoNo and Oak Grove Lake Park, and consider renting a car for day trips to experience even more.
How to find the best Chesapeake package deals?
Begin your search for a Chesapeake package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesapeake package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chesapeake adventure off to a flying start.
Is it cheaper to book a Chesapeake vacation as a package?
You can enjoy significant savings on your next Chesapeake retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chesapeake?
Land amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Chesapeake break.
How to plan a trip to Chesapeake?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you like can all impact your decision on when to visit Chesapeake.
  2. Set a budget: Factor in costs such as flights, food and transportation when working out how much to set aside for your trip to Chesapeake. Then, pick a property that fits your budget, whether that's a wallet-friendly stay or a swankier retreat.
  3. Decide your trip length: Consider how much time you want to spend discovering Chesapeake. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Chesapeake vacation package that brings all your bookings together.

Discover the most popular places to visit in Chesapeake

Lake Drummond

5/5(1 review)

Commune with nature and explore the great outdoors at Lake Drummond during your travels in Chesapeake. Stroll along the beautiful beaches in this romantic area, or check out its top-notch restaurants.

Lake Drummond
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.