Chesapeake Holidays

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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
A wooden pier extending into a calm lake, surrounded by dense trees.

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

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 1.659.676 ₫ per night from 15 Jul to 16 Jul
1.659.676 ₫
1.961.164 ₫ total
15 Jul - 16 Jul
includes taxes & fees
7.2/10 Good! (879 reviews)
"This is an inexpensive hotel stay. It is an old facility more renovations would make it nicer (ie replace shower calking, laminated floors. The sheets were clean, investment in new towels. It is wall air-conditioning and due to heat (heatwave"

Reviewed on 10 Jul 2026

STUDIOS & SUITES 4 LESS CHESAPEAKE
Hyatt Studios Chesapeake

Hyatt Studios Chesapeake

2 out of 5
101 Volvo Parkway Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is 4.604.605 ₫ per night from 27 Jul to 28 Jul
4.604.605 ₫
5.347.884 ₫ total
27 Jul - 28 Jul
includes taxes & fees
7.8/10 Good! (28 reviews)
"Great location"

Reviewed on 11 Jul 2026

Hyatt Studios Chesapeake
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
The price is 3.975.653 ₫ per night from 28 Jul to 29 Jul
3.975.653 ₫
4.819.688 ₫ total
28 Jul - 29 Jul
includes taxes & fees
7.8/10 Good! (1,891 reviews)
"Clean room beach view balcony laid back not to many people"

Reviewed on 10 Jul 2026

Wyndham Virginia Beach Oceanfront
See all 3,468 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.

Stay near popular Chesapeake attractions

A CVS store with a large archway and a red star logo.

Greenbrier Mall

8.4/10 (837 reviews)
This regional shopping centre features over 100 stores and eateries, plus a Cinema Café for dining during films. Families enjoy the supervised soft play area and convenient amenities while shopping.
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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.

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