Chesapeake Vacations from $210

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Your Chesapeake Vacation

Lock in a Chesapeake vacation package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. Greenbrier Mall, Oak Grove Lake Park and Chesapeake City Park are among the popular attractions you'll want to explore. Your perfect Chesapeake vacation is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.

The Latest Chesapeake vacation packages

Price found within the past 48 hours. Click for updated prices.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier East
Price was $256, price is now $210 per person
$210
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
17.2/10 Exceptional! (326 reviews)
We stayed one day and it got the job done. That said…the room is TINY and the breakfast is beat.

Reviewed on Nov 15, 2025

The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $806, price is now $604 per person
$604
per person
Jan 23 - Jan 25
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
8.2/10 Very Good! (1,476 reviews)
We love the homey feeling of the room. The whole apartment aka hotel room was the best. Can't wait to cone back during the warmer season. Thanks for making my birthday

Reviewed on Oct 12, 2025

The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $445, price is now $376 per person
$376
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
20/10 Exceptional! (98 reviews)
Loved our stay at the Inn. Super comfortable bed with top quality linens. Staff was very friendly and accommodating. Convenient to all the wedding activities that we were in town for. Breakfast was delicious.

Reviewed on Oct 26, 2025

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
Northeast Virginia Beach
Price was $421, price is now $366 per person
$366
per person
Dec 26 - Dec 28
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
16.8/10 Exceptional! (1,431 reviews)
It was very nice and clean. My friends and I enjoyed 419.

Reviewed on Nov 15, 2025

Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $304, price is now $264 per person
$264
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
17.2/10 Exceptional! (1,005 reviews)
We had a pretty decent stay. We stayed in the studio which was a smaller size than we expected. Nonetheless, we still had a good stay. It was a very convenient area as far as food and activities. Our concierge was also great as well. We will definitely be back.

Reviewed on Nov 13, 2025

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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

1 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 Jillian's Billiards.

Find hotels in Greenbrier East

Discover the most popular places to visit in Chesapeake

Greenbrier Mall

Greenbrier Mall

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

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

What to do in Chesapeake

Virginia Zoo

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

$40
per adult
80% of travellers recommend
Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin
View of the water and the Spirit of Norfolk Dinner Cruise ship

City Cruises Norfolk: Signature Dinner Cruise

$172
per adult
72% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
Wetland Zip Tour

Wetland Zip Tour

$65
per adult
98% of travellers recommend
Wetland Zip Tour
See all activities in Chesapeake

Chesapeake Hotel Deals

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $99 total per night from Nov 18 to Nov 19
$99 total
Nov 18 - Nov 19
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
The staff was pleasant and friendly the room was clean and breakfast was excellent

Reviewed on Nov 14, 2025

Comfort Suites Chesapeake - Norfolk
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
$61 nightly
The price is $73 total per night from Nov 17 to Nov 18
$73 total
Nov 17 - Nov 18
Total with taxes and fees
6.6/10 (635 reviews)
I think my favorite part is the TV. Lol. Front desk attendants are very nice and polite. Housekeeping seems friendly. Overall nice place to stay.

Reviewed on Nov 12, 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
$79 nightly
The price is $93 total per night from Nov 23 to Nov 24
$93 total
Nov 23 - Nov 24
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Great

Reviewed on Nov 6, 2025

Wingate by Wyndham Chesapeake
See all 3,425 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.

Find the Best Chesapeake Vacation Packages

Chesapeake Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Population
235,400
Max Temp Winter
50ºF
Max Temp Summer
85ºF
Top Sights
Portlock Galleries at SoNo, Jillians Billiards and Chesapeake City Park

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Frequently asked questions

How much does a Chesapeake vacation package cost?
You'll find cheap prices from $210 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?
December, January and February are great times to look for cheap Chesapeake vacation packages. Choosing to travel in less busy months means you can typically find lower prices on flights and accommodations.
How many days is enough for Chesapeake?
Chesapeake vacations can be short or long, but to really get a feel for this destination, we'd say 2 days is about right. In this timeframe, you can visit major attractions like Chesapeake City Park and Oak Grove Lake Park as well as underrated spots. Don't miss out on cool neighborhoods such as Greenbrier East and Greenbrier West either. If you're smart with your time, you can even schedule a day trip outside of Chesapeake too.
Is it worth booking a vacation package to Chesapeake?
Chesapeake has all the ingredients you need for a fantastic break — history, nature and hiking are just the start. Whether you want to visit sights like Oak Grove Lake Park and Portlock Galleries at SoNo, or take the path less traveled, you'll have plenty to see and do on your Chesapeake vacation.
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 when to get away: Check your diary and get your bags packed. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Chesapeake.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and dining out to activities and flights. Your hotel will likely be the biggest expense during your trip to Chesapeake.
  3. Use Expedia's trip planning tool to discover Chesapeake: Research every aspect of your trip to Chesapeake with this handy planner. Invite family or friends to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Determine how many days away: Start by making a list of all the activities and attractions you want to experience in Chesapeake. Then, estimate how long you'll need for each, as well as any travel time.
  5. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Chesapeake vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Take a look at our dedicated travel guide to find some fun things to do in Chesapeake. Book tickets or make reservations before you go to save time and avoid the stress of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Chesapeake vacation packages?
Your Chesapeake getaway should be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.