Chesapeake City County Vacations & Trips from $298

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Your Chesapeake City County Vacation

Leave the planning to us with a Chesapeake City County vacation package. With everything organized before you leave home, the only thing left for you to do is relax and experience this destination's beauty and culture. Not sure where your first stop should be? Chesapeake is among the most popular cities to visit during a trip to Chesapeake City County. Expedia has hotels, flights and all your other travel needs to help you put together your very own customized Chesapeake City County vacation today.

Top destinations in Chesapeake City County

A golf course, a large building complex, and a marina by a river.

Chesapeake

Chesapeake

The Latest Chesapeake City County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

Northeast Virginia Beach
Save 100% on your flight
$298
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (1,002 reviews)
The stuffs are just awesome. Always presenting themselves with a nice smile. We had a very minor issue in our room. The maintenance was there with in 10 mins. Overall, we really enjoyed our stay.

Reviewed on Aug 21, 2026

Sea Ranch Resort

Sea Ranch Resort

Save 100% on your flight
$496
per person
Sep 22 - Sep 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.4/10 Very Good! (1,009 reviews)
Cleanliness was definitely lacking, there were stains on the curtains, dead bugs (on headboard and dead fly on outside table). Rust was also an issue, the balcony and door to balcony was riddled with rust. Main elevator was down, we were able to use staff elevator, however it was tiny. Also, at one point I leaned on the handrail while I was chatting with someone and nearly fell off the fourth floor. One of the posts to the handrail was extremely loose, which we called the front desk and let them know (they put caution tape on for the 2 days, still there when we left). I felt icky staying here and will not return.

Reviewed on Aug 19, 2026

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Northeast Virginia Beach
Save 100% on your flight
$405
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.4/10 Very Good! (1,486 reviews)
Very peaceful and calming!

Reviewed on Aug 22, 2026

Blackbeard's Lodge

Blackbeard's Lodge

Save 100% on your flight
$613
per person
Oct 3 - Oct 10
just found
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.4/10 Very Good! (384 reviews)
Great place , friendly infomative staff. Classic original hotel.

Reviewed on Aug 22, 2026

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

Save 100% on your flight
$332
per person
Oct 2 - Oct 4
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9.2/10 Wonderful! (1,920 reviews)
Had the best stay!! We did have issues with all the stairs with my elderly mother. Staff was able to move us to the first floor the next day after checkin. Loved the beach access and parking. Very close to so many things in the area.

Reviewed on Aug 22, 2026

Find the Best Chesapeake City County Vacation Packages

Chesapeake City County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norfolk Intl. Airport (ORF)
Top Sights
Chesapeake City Park, Oak Grove Lake Park and Lake Drummond

Chesapeake City County Hotel Deals

Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

5700 Atlantic Ave Virginia Beach VA
Fully refundableReserve now, pay when you stay
$100 nightly
$117 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (2,018 reviews)
"Daytime staff were friendly and helpful, nighttime staff seemed as if he was high and didnt care to help with any issue at all. Room had odor of cat pee and their only offer of help was to "spray the room" while we went out for a few hours. The barn doors for the master bedroom were off track and ..."

Reviewed on Aug 22, 2026

Wyndham Virginia Beach Oceanfront
Ocean Resort

Ocean Resort

Atlantic Avenue,2417 Virginia Beach VA
Fully refundableReserve now, pay when you stay
$101 nightly
$118 total
Sep 20 - Sep 21
Total with taxes and fees
7.8/10 Good! (1,710 reviews)
"I recommend this property the staff was very nice and helpful. The hotel was around a lot of shops and restaurants."

Reviewed on Aug 22, 2026

Ocean Resort
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

4453 Bonney Rd Virginia Beach VA
Fully refundable
$93 nightly
$109 total
Sep 7 - Sep 8
Total with taxes and fees
Crowne Plaza Virginia Beach Town Center by IHG
See all 3,494 properties in Chesapeake City County
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 City County attractions

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

Greenbrier Mall

8.4/10 (837 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.
See properties
A building with a clock tower, surrounded by pink flowers and greenery.

Chesapeake Square Mall

8.2/10 (429 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.
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A modern building with a curved glass facade and a sign reading "Chesapeake Conference Center."

Chesapeake Conference Center

7.8/10 (169 reviews)
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.
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A wooden bridge over a calm river surrounded by dense forest.

Chesapeake City Park

8.2/10 (180 reviews)
Chesapeake City Park is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? Stroll along the area's beautiful beaches or experience its acclaimed theater scene.
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A solitary tree in a swampy area with water around its base.

Lake Drummond

7.8/10 (12 reviews)
Commune with nature and explore the great outdoors at Lake Drummond during your travels in Chesapeake. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.
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A wooden pier extending into a calm lake, surrounded by dense trees.
Photo by Kaylee Spinhirn

Oak Grove Lake Park

7.6/10 (39 reviews)
After visiting Oak Grove Lake Park, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music or attend a sporting event.
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Chesapeake Arboretum

7.6/10 (76 reviews)
Enjoy an outing to Chesapeake Arboretum during your stay in Chesapeake. Amble around the area's beautiful beaches or attend a sporting event.
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Dismal Swamp Canal

Dismal Swamp Canal is just one of the places to see in Chesapeake, so why not enjoy the other things to explore during your travels? While in this family-friendly area, you can enjoy the coffeehouses.
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What to do in Chesapeake City County

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

Norfolk's Combo Tickets - Virginia Zoo & Battleship Wisconsin

$43
per adult
100% 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

$103
per adult
76% of travellers recommend
City Cruises Norfolk: Signature Dinner Cruise
View of Spirit of Norfolk

City Cruises Norfolk: Signature Brunch Cruise

$97
per adult
88% of travellers recommend
City Cruises Norfolk: Signature Brunch Cruise
See all activities in Chesapeake City County
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