Deals on vacations and trips to Chesapeake City County

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Chesapeake Square Mall

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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 $331, price is now $281 per person
$281
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Hilton Norfolk The Main

Hilton Norfolk The Main

4 out of 5
Downtown Norfolk
Save 100% on your flight
Price was $813, price is now $652 per person
$652
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
This hotel features 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking. You'll appreciate the a rooftop terrace, bar/lounge, and convenience store.
Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $1,686, price is now $1,383 per person
$1,383
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
The Sanderling

The Sanderling

4 out of 5
Price was $754, price is now $632 per person
$632
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $1,032, price is now $865 per person
$865
per person
Oct 4 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Norfolk (ORF)
A restaurant and a bar/lounge are featured at this bed & breakfast. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A terrace, a garden, and a snack bar/deli are also on offer.

Top Chesapeake City County hotels deals

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
Free Cancellation
$128 nightly
The price is $149 total per night
$149 total
Sep 1 - Sep 2
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, Ascend Hotel Collection

Surfbreak Virginia Beach Oceanfront, Ascend Hotel Collection

3 out of 5
1101 Atlantic Ave, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $99 total per night
$99 total
Sep 21 - Sep 22
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
Wyndham Virginia Beach Oceanfront

Wyndham Virginia Beach Oceanfront

3 out of 5
5700 Atlantic Ave, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
$97 nightly
The price is $113 total per night
$113 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A bar/lounge, a 24-hour front desk, and a terrace are also provided.
Pool
Pet friendly
DoubleTree by Hilton Virginia Beach

DoubleTree by Hilton Virginia Beach

4 out of 5
1900 Pavilion Dr, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
$108 nightly
The price is $127 total per night
$127 total
Sep 4 - Sep 5
Total with taxes and fees
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-out are also provided.
Pool
Pet friendly
Hyatt Place Virginia Beach Town Center

Hyatt Place Virginia Beach Town Center

3 out of 5
335 Independence Blvd, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $157 total per night
$157 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Pet friendly
Oceans 2700

Oceans 2700

2.5 out of 5
2700 Pacific Avenue, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $89 total per night
$89 total
Sep 2 - Sep 3
Total with taxes and fees
A seasonal outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
Pool
Parking included
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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

Chesapeake Square Mall
Chesapeake Square Mall
Chesapeake Conference Center
Chesapeake Conference Center
Chesapeake Conference Center

Frequently asked questions

How much are vacation packages to Chesapeake City County?
Starting from as low as $281, 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.