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.
James River Inn & Suites

James River Inn & Suites

2.5 out of 5
Briarfield
Price was CA $1,068, price is now CA $977 per person
CA $977
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Stay at this hotel in Newport News. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Hampton Coliseum and Virginia War Museum are located nearby.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Price was CA $1,857, price is now CA $1,510 per person
CA $1,510
per person
Dec 27 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
Book a stay at this beach aparthotel 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.
The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was CA $2,714, price is now CA $2,373 per person
CA $2,373
per person
Dec 27 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
Stay at this B&B in Norfolk. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Waterside District and Pagoda and Oriental Garden are located nearby.
Residence Inn by Marriott Norfolk Airport

Residence Inn by Marriott Norfolk Airport

3 out of 5
Price was CA $1,634, price is now CA $1,464 per person
CA $1,464
per person
Dec 27 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Norfolk. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Waterside District and Norfolk Premium Outlets are located nearby.
Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

Holiday Inn Express Hotel & Suites Norfolk Airport by IHG

2.5 out of 5
Price was CA $1,542, price is now CA $1,411 per person
CA $1,411
per person
Dec 27 - Jan 3
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Norfolk (ORF)
Book a stay at this business-friendly hotel in Norfolk. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Waterside District and Greenbrier Mall are located nearby.

Top Chesapeake City County hotels deals

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
Oct 18 - Oct 19
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
Free cancellation
The price is CA $114 per night
CA $114
CA $134 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 $175 total
Oct 19 - Oct 20
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 $54 per night
CA $54
CA $88 total
Nov 2 - Nov 3
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
Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave Virginia Beach VA
The price is CA $86 per night
CA $86
CA $101 total
Nov 4 - Nov 5
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 convenient parking in our reviews. Popular attractions Virginia Beach Boardwalk and Sandbridge Beach 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 9 - Nov 10
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.
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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 $977, 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.