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

2 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 Chesapeake City Park.

Find hotels in Greenbrier East

Find the Best Chesapeake Vacation Packages

Chesapeake Hotel Deals

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 AED 259 per night from Apr 3 to Apr 4
AED 259
AED 302 total
includes taxes & fees
3 Apr - 4 Apr
8/10 Very Good! (1,010 reviews)
"The hot tub and heated pool year round is the reason we come. The staff is okay, not the friendliest... The room is okay, some have a little wear and tear. Breakfast is bomb too! 👌😁Usually eggs, biscuits and gravy, waffles you make yourself, cereal, bagels, and fruit. Solid 4."

Reviewed on 21 February 2025

Wingate by Wyndham Chesapeake
SpringHill Suites by Marriott Chesapeake Greenbrier
SpringHill Suites by Marriott Chesapeake Greenbrier
3 out of 5
1446 Crossways Blvd, Chesapeake, VA
The price is AED 345 per night from Mar 9 to Mar 10
AED 345
AED 401 total
includes taxes & fees
9 Mar - 10 Mar
8.2/10 Very Good! (1,001 reviews)
"N/a."

Reviewed on 2 March 2025

SpringHill Suites by Marriott Chesapeake Greenbrier
Holiday Inn Express Chesapeake - Norfolk, an IHG Hotel
Holiday Inn Express Chesapeake - Norfolk, an IHG Hotel
2.5 out of 5
721 Conference Center Drive, Chesapeake, VA
Fully refundable
The price is AED 345 per night from Mar 16 to Mar 17
AED 345
AED 401 total
includes taxes & fees
16 Mar - 17 Mar
8.6/10 Excellent! (1,002 reviews)
Gr8
"Front desk check in was one of the best Missing hard boiled eggs, guessing due to shortage"

Reviewed on 25 February 2025

Holiday Inn Express Chesapeake - Norfolk, an IHG Hotel
See all 3,445 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