Chesapeake Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

Photo by Kaylee Spinhirn
    deals illustration

    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Chesapeake

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

Greenbrier

4 out of top 10 points of interest in this area

While visiting Greenbrier, you might make a stop by sights like Greenbrier Mall and Chesapeake Arboretum.

Find hotels in Greenbrier

Top hotels in Chesapeake

Red Roof Inn Chesapeake Conference Center
Red Roof Inn Chesapeake Conference Center
2 out of 5
724 Woodlake Dr, Chesapeake, VA
Fully refundableReserve now, pay when you stay
The price is ฿2,743 per night from 16 Jul to 17 Jul
฿2,743
฿3,219 total
16 Jul - 17 Jul
includes taxes & fees
6.8/10 (1,000 reviews)
"The room overall was is decent shape and was clean. It was a little dated but a great value for the price. The only thing I was say negatively is that the tub is REALLY slick and was a fall hazard and there was a gap under the door for creepy crawlers."

Reviewed on 3 Jul 2025

Red Roof Inn Chesapeake Conference Center
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 ฿2,088 per night from 20 Jul to 21 Jul
฿2,088
฿2,466 total
20 Jul - 21 Jul
includes taxes & fees
6.4/10 (444 reviews)
"Beautiful and comfortable upgraded rooms!"

Reviewed on 10 Jul 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
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 ฿3,557 per night from 20 Jul to 21 Jul
฿3,557
฿4,156 total
20 Jul - 21 Jul
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"Great stay"

Reviewed on 10 Jul 2025

Wingate by Wyndham Chesapeake
See all 3,426 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.

Popular places to visit

Lake Drummond

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

Lake Drummond

What to do in Chesapeake

Wetland Zip Tour

Wetland Zip Tour

฿2,137
per adult
98% of travellers recommend
Wetland Zip Tour
Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

฿4,544
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

฿1,321
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
See all activities in Chesapeake

Frequently asked questions

How much does a Chesapeake holiday 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 holiday to Chesapeake costs.
What are the cheapest months to go to Chesapeake?
If you'd like to book a cheap Chesapeake holiday package, consider planning a trip in January, February and November. You'll generally find better prices on accommodation and flights during these months --- perfect for travellers wishing to save money.
How many days is enough for Chesapeake?
Chesapeake holidays 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 neighbourhoods 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 holiday package to Chesapeake?
Well known for its nature, adventure sports and hiking, a Chesapeake holiday 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 holiday as a package?
You can enjoy significant savings on your next Chesapeake retreat by booking a customised holiday 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 holiday 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, favourite 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 holiday 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.