Chesapeake Vacations from $296

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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.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $441, price is now $296 per person
$296
per person
Nov 8 - Nov 12
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,006 reviews)
The only thing that I would recommend is changing the sleep sofa! It was terrible we were not able to sleep in it . This would be my new location since I visit VA beach yearly

Reviewed on Aug 20, 2025

Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $469, price is now $309 per person
$309
per person
Nov 8 - Nov 12
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,661 reviews)
Property needs some updating but was very clean and staff was friendly and helpful.

Reviewed on Aug 22, 2025

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $439, price is now $319 per person
$319
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,005 reviews)
Conveniently located and easy access to beach. safe surroundings and great for families.

Reviewed on Aug 22, 2025

The Capes Hotel

The Capes Hotel

3 out of 5
Northeast Virginia Beach
Price was $413, price is now $302 per person
$302
per person
Sep 27 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (357 reviews)
Great place to stay. Room was clean. Staff was friendly and helpful. We will come again.

Reviewed on Aug 19, 2025

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $722, price is now $536 per person
$536
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,753 reviews)
Wonderful friendly helpful staff. Good breakfast. Comforting facilities.

Reviewed on Aug 23, 2025

Don't see what you're looking for?
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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

4/5(260 reviews)

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

4/5(76 reviews)

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

Deck area aboard the Spirit of Norfolk Dinner Cruise in Virginia

Spirit of Norfolk Signature Dinner Cruise

$139
per adult
72% of travellers recommend
Spirit of Norfolk Signature Dinner Cruise
Picture 15 for Activity Virginia Beach: Neptune Ghosts Haunted Walking Tour

Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours

$24
per adult
Buried Beneath the Boardwalk: Neptune Ghouls and Ghost Tours
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
See all activities in Chesapeake

Chesapeake Hotel Deals

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
$53 nightly
The price is $63 total per night from Sep 9 to Sep 10
$63 total
Sep 9 - Sep 10
Total with taxes and fees
6.6/10 (514 reviews)
"The room was clean and the bed was excellent. The blanket was more like a sheet than a blanket. But overall it was a peaceful stay."

Reviewed on Aug 21, 2025

STUDIOS & SUITES 4 LESS CHESAPEAKE
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA

3 out of 5
1801 Atlantic Ave, Virginia Beach, VA
Fully refundable
$128 nightly
The price is $149 total per night from Sep 1 to Sep 2
$149 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (2,253 reviews)
"Good"

Reviewed on Aug 22, 2025

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $99 total per night from Sep 21 to Sep 22
$99 total
Sep 21 - Sep 22
Total with taxes and fees
8.2/10 Very Good! (1,080 reviews)
"I didn't care that you couldn't park right on this property. The pool was cloudy for most of our stay but the hotel was clean"

Reviewed on Aug 21, 2025

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection
See all 3,420 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.

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Frequently asked questions

How much does a Chesapeake vacation package cost?
You'll find cheap prices from $296 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.