Deals on vacations and trips to Chesapeake City County

Save when you book Chesapeake City County, VA package deals

Choose two or more items and save on your trip:

Search vacation packages deals in Chesapeake City County's top destinations

Colorful sunset over riverside resort in Cambridge Maryland USA

Chesapeake

Vacations
Chesapeake

Chesapeake City County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Price was $709, price is now $509 per person
$509
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Families will appreciate the playground and barbecue grills. There's an outdoor pool on site, and a terrace and a picnic area are also provided.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $990, price is now $673 per person
$673
per person
May 13 - May 17
found 5 hours ago
Roundtrip non-stop flight included
Cedar Rapids (CID) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A business center, express check-out, and laundry facilities are also on offer.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $2,084, price is now $1,446 per person
$1,446
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Family-friendly amenities include a children's pool and kid-friendly dining, along with kayaking.
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier East
Save 100% on your flight
Price was $805, price is now $574 per person
$574
per person
May 28 - Jun 3
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Norfolk (ORF)
A gym is featured at this hotel, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A 24-hour business center, express check-in, and express check-out are also on offer.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $977, price is now $731 per person
$731
per person
May 22 - May 25
found 14 hours ago
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference center. Enjoy the gym and perks like free self parking.

Top Chesapeake City County hotels deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle Chesapeake VA
Free Cancellation
Reserve now, pay when you stay
$82 nightly
The price is $96 total per night
$96 total
Mar 29 - Mar 30
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront)

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

3 out of 5
1801 Atlantic Ave Virginia Beach VA
$108 nightly
The price is $127 total per night
$127 total
Mar 22 - Mar 23
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free on-the-go breakfast each morning.
Pool
Breakfast included
Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

3 out of 5
1101 Atlantic Ave Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $109 total per night
$109 total
Apr 7 - Apr 8
Total with taxes and fees
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Guests will appreciate free perks like free self parking and WiFi in public areas.
Pool
Parking included
Hilton Vacation Club Ocean Beach Club Virginia Beach

Hilton Vacation Club Ocean Beach Club Virginia Beach

3.5 out of 5
3401 Atlantic Ave Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
$92 nightly
The price is $108 total per night
$108 total
Mar 24 - Mar 25
Total with taxes and fees
This smoke-free hotel features 2 indoor pools, an outdoor pool, and a restaurant. Enjoy the 24-hour gym and perks like free WiFi. There's a beach bar on site, and laundry facilities and concierge services are also provided.
Pool
Free WiFi
Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave Virginia Beach VA
$59 nightly
The price is $70 total per night
$70 total
Mar 24 - Mar 25
Total with taxes and fees
A seasonal outdoor pool, free self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. A safe deposit box is provided and the front desk is staffed around-the-clock.
Pool
Parking included
Hyatt Place Virginia Beach / Oceanfront

Hyatt Place Virginia Beach / Oceanfront

3 out of 5
3601 ATLANTIC AVENUE Virginia Beach VA
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $147 total per night
$147 total
Mar 24 - Mar 25
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Enjoy the seasonal outdoor pool and free buffet breakfast each morning.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Chesapeake City County
View all properties
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.

Photos of local treasures

Browse Chesapeake City County vacation photos for more inspiration

Greenbrier Mall
Greenbrier Mall
Greenbrier Mall
Chesapeake Conference Center
Chesapeake Conference Center

Frequently asked questions

How much are vacation packages to Chesapeake City County?
Starting from as low as $509, hotel and flight packages are the perfect way to stretch your travel budget. Chesapeake City County, here you come!
Where can I get the best vacation package deals for Chesapeake City County?
You'll come across an excellent range of Chesapeake City County package deals on Travelocity. With as many as 400 airlines and 1,000,000 properties worldwide, arranging the ultimate escape will be simple.
Why should I book my Chesapeake City County vacation bundle via Travelocity?
You'll not only enjoy big savings, but you'll also have access to our 24/7 customer support, top-notch service and a Price Match Guarantee. Explore every nook-and-cranny across the world, discover hidden treasures and create unforgettable memories — we'll take care of the important details.
Can I save money on my Chesapeake City County car rental if I combine it with a hotel or flight?
Certainly. And our Chesapeake City County vacation packages are the ideal way to do it. In just a few clicks you can save cash and time by booking everything in one place. Collect the keys to your rental car and feel the freedom of the open road. Need to fill your itinerary? Add a few tours to your package and make savings on those too.
Which airport is best for Chesapeake City County?
Traveling to Chesapeake City County will see you step off the plane at Norfolk Intl. Airport (ORF) or Newport News - Williamsburg Intl. Airport (PHF).
What is there to do in Chesapeake City County?
Chesapeake City County boasts hidden gems at every corner, however make sure you plan a trip to Chesapeake City Park and Chesapeake City Hall while you're in town. These two attractions shouldn't be missed.

Explore More Ways to Travel with Travelocity