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

1 out of top 10 points of interest in this area
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

STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is ￥7,736 per night from Aug 26 to Aug 27
￥7,736
￥9,190 total
Aug 26 - Aug 27
includes taxes & fees
6.6/10 (524 reviews)
Great for one night!
"Great for one night to attend the jazz festival in Norfolk. The very large dumpsters lowered my rating."

Reviewed on Aug 23, 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
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 ￥18,750 per night from Sep 1 to Sep 2
￥18,750
￥21,857 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (2,267 reviews)
"Amazing stay. We have a special needs child and staff was very understanding and kind."

Reviewed on Aug 25, 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
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 ￥12,365 per night from Sep 21 to Sep 22
￥12,365
￥14,515 total
Sep 21 - Sep 22
includes taxes & fees
8.2/10 Very Good! (1,089 reviews)
Pleasant stay
"I really enjoyed myself at this hotel. It was very clean. The staff was very friendly and very knowledgeable. I will be returning back soon."

Reviewed on Aug 24, 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
See all 3,420 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.

What to do in Chesapeake

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

￥16,462
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

￥5,983
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
Picture 15 for Activity Virginia Beach: Neptune Ghosts Haunted Walking Tour

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

￥3,547
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
See all activities in Chesapeake

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.

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