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
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South Norfolk

South Norfolk might not have many top sights, but Chesapeake Conference Center and Greenbrier Mall are two attractions nearby that you can check out.

Find hotels in South Norfolk

Find the Best Chesapeake Vacation Packages

Chesapeake Hotel Deals

Holiday Inn Express Chesapeake - Norfolk by IHG
Holiday Inn Express Chesapeake - Norfolk by IHG
2.5 out of 5
721 Conference Center Drive, Chesapeake, VA
Fully refundable
The price is SAR 409 per night from Apr 28 to Apr 29
SAR 409
SAR 474 total
includes taxes & fees
28 Apr - 29 Apr
8.6/10 Excellent! (1,001 reviews)
"We liked everything"

Reviewed on 21 April 2025

Holiday Inn Express Chesapeake - Norfolk by IHG
TRU by Hilton Chesapeake, VA
TRU by Hilton Chesapeake, VA
2.5 out of 5
1570 CROSSWAYS BLVD, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is SAR 379 per night from May 18 to May 19
SAR 379
SAR 439 total
includes taxes & fees
18 May - 19 May
8.8/10 Excellent! (174 reviews)
"Nice hotel"

Reviewed on 23 April 2025

TRU by Hilton Chesapeake, VA
Wingate by Wyndham Chesapeake
Wingate by Wyndham Chesapeake
2.5 out of 5
817 Greenbrier Circle, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is SAR 353 per night from Apr 29 to Apr 30
SAR 353
SAR 409 total
includes taxes & fees
29 Apr - 30 Apr
8/10 Very Good! (1,001 reviews)
Don’t skip this hotel!!
"We loved our stay. The breakfast is where this hotel shines. My daughter who is only a morning herbal tea drinker was impressed there was something other than black tea. This is now our new monthly hotel when we go for hockey games!"

Reviewed on 21 April 2025

Wingate by Wyndham Chesapeake
See all 3,359 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 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

Greenbrier Mall

Greenbrier Mall

4/5(260 reviews)

You can browse for the perfect souvenirs at Greenbrier Mall during your visit to Chesapeake. Stroll along the beautiful beaches or attend a sporting event in the area.

Greenbrier Mall
Chesapeake Square Mall

Chesapeake Square Mall

4/5(76 reviews)

You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Chesapeake Square Mall
Chesapeake Conference Center

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theater scene.

Chesapeake Conference Center