Chesapeake City County Vacation Packages 2025/2026 from $278

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

Chesapeake

Vacations

Chesapeake City County flight + hotel vacation packages

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

Beach Quarters Resort

Northeast Virginia Beach

$278

per person

Nov 14 - Nov 17

found 21 hours ago

Roundtrip non-stop flight included

New York (NYC) to Norfolk (ORF)

This hotel features an indoor pool and a gym. Enjoy the outdoor tennis court and perks like free WiFi. There's a seasonal outdoor pool on site, and a 24-hour front desk and a rooftop terrace are also provided.

Sanderling Resort Residences

Save 100% on your flight

$1,007

per person

Dec 18 - Dec 22

just found

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.

The Sanderling

Save 100% on your flight

$1,303

per person

Dec 16 - Dec 23

found 12 hours ago

Roundtrip flight included

Boise (BOI) 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.

Ocean Sands Beach Boutique Inn - Stay At the Beach

$454

per person

Dec 16 - Dec 23

found 12 hours ago

Roundtrip flight included

Boise (BOI) 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 onsite laundry facilities and in-room childcare. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area.

Boardwalk Resort and Villas

Northeast Virginia Beach

$281

per person

Nov 14 - Nov 17

found 21 hours ago

Roundtrip non-stop flight included

New York (NYC) 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.

Top Chesapeake City County hotels deals

Delta Hotels by Marriott Virginia Beach Waterfront Suites

2800 Shore Drive, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$98 nightly

$115 total

Oct 26 - Oct 27

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 conveniences like a 24-hour front desk and laundry facilities.

Pool

Pet friendly

Schooner Inn

215 Atlantic Ave, Virginia Beach, VA

$57 nightly

$68 total

Nov 3 - Nov 4

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

Oceans 2700

2700 Pacific Avenue, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$64 nightly

$76 total

Oct 14 - Oct 15

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

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$67 nightly

$79 total

Oct 26 - Oct 27

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

3401 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$106 nightly

$124 total

Nov 2 - Nov 3

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

Hyatt Place Virginia Beach Town Center

335 Independence Blvd, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$125 total

Nov 2 - Nov 3

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

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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.

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Frequently asked questions

How much are vacation packages to Chesapeake City County?

Starting from as low as $278, 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.