Deals on vacations and trips to Chesapeake City County

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Chesapeake

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Chesapeake

Chesapeake City County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $806, price is now $524 per person
$524
per person
Apr 29 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $1,413, price is now $837 per person
$837
per person
Apr 29 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
A full-service spa, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Enjoy the 2 hot tubs and perks like free WiFi.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $824, price is now $527 per person
$527
per person
Apr 30 - May 4
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $1,105, price is now $717 per person
$717
per person
Apr 29 - May 5
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $2,798, price is now $1,894 per person
$1,894
per person
Apr 26 - May 1
found 10 hours ago
Roundtrip flight included
Boston (BOS) 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.

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 19 - Mar 20
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.
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
$125 nightly
The price is $146 total per night
$146 total
Mar 17 - Mar 18
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.
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
Free Cancellation
$107 nightly
The price is $125 total per night
$125 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.
Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave Virginia Beach VA
$60 nightly
The price is $72 total per night
$72 total
Mar 15 - Mar 16
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.
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
$81 nightly
The price is $95 total per night
$95 total
Mar 15 - Mar 16
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.
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
Mar 29 - Mar 30
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.
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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
Greenbrier Mall
Chesapeake Conference Center

Frequently asked questions

How much are vacation packages to Chesapeake City County?
Starting from as low as $524, 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.

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