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
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Greenbrier West

2 out of top 10 points of interest in this area

While visiting Greenbrier West, you might make a stop by sights like Oak Grove Lake Park and Rivercrest Play Area.

Find hotels in Greenbrier West

Top hotels in 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 S$106 per night from 2 Jan to 3 Jan
S$106
includes taxes & fees
2 Jan - 3 Jan,2025
7.8/10 Good! (1,001 reviews)
"A great blessing"

Reviewed on 9 Dec,2024

Wingate by Wyndham Chesapeake
Delta Hotels by Marriott Virginia Beach Waterfront
Delta Hotels by Marriott Virginia Beach Waterfront
4 out of 5
2800 Shore Drive, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
The price is S$169 per night from 6 Jan to 7 Jan
S$169
includes taxes & fees
6 Jan - 7 Jan,2025
8.4/10 Very Good! (1,109 reviews)
"Booked last minute for a tournament overnight and enjoyed the service and staff."

Reviewed on 27 Dec,2024

Delta Hotels by Marriott Virginia Beach Waterfront
Schooner Inn
Schooner Inn
2 out of 5
215 Atlantic Ave, Virginia Beach, VA
The price is S$112 per night from 12 Jan to 13 Jan
S$112
includes taxes & fees
12 Jan - 13 Jan,2025
8.6/10 Excellent! (2,833 reviews)
"We had a very nice time. Thanks"

Reviewed on 23 Dec,2024

Schooner Inn
See all 3,443 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 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.

What to do in Chesapeake

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

S$165
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Ziplining and Climbing at The Adventure Park at Virginia Aquarium

Ziplining and Climbing at The Adventure Park at Virginia Aquarium

S$87
per adult
Ziplining and Climbing at The Adventure Park at Virginia Aquarium
Visit Norfolk's Perk Up Pass

Visit Norfolk's Perk Up Pass

S$23
per adult
Visit Norfolk's Perk Up Pass
See all activities in Chesapeake

* 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.