Chesapeake Holidays

Photo by Kaylee Spinhirn

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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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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 S$129 per night from 7 Aug to 8 Aug
S$129
7 Aug - 8 Aug
includes taxes & fees
7/10 Good! (1,001 reviews)
"It was affordable and within a good range of everything needed. The staff was welcoming."

Reviewed on 28 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 S$81 per night from 3 Aug to 4 Aug
S$81
3 Aug - 4 Aug
includes taxes & fees
6.4/10 (484 reviews)
"Great"

Reviewed on 31 Jul, 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
Holiday Inn & Suites Virginia Beach North Beach by IHG

Holiday Inn & Suites Virginia Beach North Beach by IHG

3 out of 5
3900 Atlantic Avenue, Virginia Beach, VA
Fully refundable
The price is S$283 per night from 1 Sept to 2 Sept
S$283
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (1,011 reviews)
"Great place to stay next to board walk and walking distance to stores!"

Reviewed on 30 Jul, 2025

Holiday Inn & Suites Virginia Beach North Beach by IHG
See all 3,457 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

S$160
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

S$52
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

S$41
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.