Book Exclusive Chesapeake City County Vacation Packages

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Chesapeake City County flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Sunrise Inn By OYO Newport News US-60

Sunrise Inn By OYO Newport News US-60

2.5 out of 5
North Newport News
Price was CA $1,091, price is now CA $956 per person
CA $956
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
Stay at this hotel in Newport News. Enjoy free WiFi, free parking, and room service. Popular attractions Bounce House and Newport News Park are located nearby.
The Lodge at Kiln Creek Resort

The Lodge at Kiln Creek Resort

3.5 out of 5
Central Newport News
Price was CA $2,039, price is now CA $1,785 per person
CA $1,785
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
Book a stay at this golf hotel in Newport News. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Patrick Henry Mall and Hampton Roads Iceplex are located nearby.
Sonesta Simply Suites Hampton

Sonesta Simply Suites Hampton

3 out of 5
Price was CA $1,206, price is now CA $1,082 per person
CA $1,082
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Hampton. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hampton Coliseum and Boo Williams Sportplex are located nearby.
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
Central Newport News
Price was CA $1,145, price is now CA $1,029 per person
CA $1,029
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
Book a stay at this beach hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bounce House and Patrick Henry Mall are located nearby.
The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Price was CA $1,078, price is now CA $972 per person
CA $972
per person
Nov 20 - Nov 23
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.

Top Chesapeake City County hotels deals

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd Chesapeake VA
Free cancellation
The price is CA $117 per night
CA $117
CA $138 total
Nov 15 - Nov 16
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Pool
Breakfast 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
The price is CA $101 per night
CA $101
CA $160 total
Nov 3 - Nov 4
includes taxes & fees
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, 2 indoor pools, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
Pool
Free WiFi
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
The price is CA $120 per night
CA $120
CA $141 total
Oct 18 - Oct 19
includes taxes & fees
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
Pool
Parking included
Hilton Vacation Club Oceanaire Virginia Beach

Hilton Vacation Club Oceanaire Virginia Beach

3.5 out of 5
3421 Atlantic Ave Virginia Beach VA
Free cancellation
Reserve now, pay when you stay
The price is CA $114 per night
CA $114
CA $174 total
Oct 18 - Oct 19
includes taxes & fees
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
Pool
Free WiFi
Sundial Inn

Sundial Inn

2 out of 5
308 21st St Virginia Beach VA
Free cancellation
Reserve now, pay when you stay
The price is CA $53 per night
CA $53
CA $87 total
Oct 18 - Oct 19
includes taxes & fees
Stay at this motel in Virginia Beach. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and First Landing State Park are located nearby.
Pool
Parking included
Crowne Plaza Virginia Beach Town Center by IHG

Crowne Plaza Virginia Beach Town Center by IHG

3.5 out of 5
4453 Bonney Rd Virginia Beach VA
Free cancellation
The price is CA $107 per night
CA $107
CA $126 total
Nov 12 - Nov 13
includes taxes & fees
Book a stay at this business-friendly hotel in Virginia Beach. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Veterans United Home Loans Amphitheater at Virginia Beach and Virginia Beach Sportsplex are located nearby.
Pool
Free WiFi
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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.

Stay near popular Chesapeake City County attractions

A large building with a prominent arched entrance and a green roof.

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

Photos of local treasures

Browse Chesapeake City County vacation photos for more inspiration

A large building with a prominent arched entrance and a green roof.
A building with a large arched entrance, surrounded by trees and a parking lot.
A building with a large arched entrance, a sign reading "Dillard's," and well-maintained landscaping.
A modern building with a curved facade and a sign reading "Chesapeake Conference Center".
A modern building with a curved glass facade and a sign reading "Chesapeake Conference Center."

Frequently asked questions

How much are vacation packages to Chesapeake City County?
Starting from as low as CA $956, 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.