Chesapeake Vacation Packages 2025/2026 from $404

Chesapeake flight + hotel vacation packages

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

Boardwalk Resort and Villas

Northeast Virginia Beach

$404

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) 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.

The Capes Hotel

Northeast Virginia Beach

$434

per person

Sep 26 - Sep 28

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Norfolk (ORF)

A restaurant and an indoor pool are featured at this hotel. WiFi in public areas is free. Self parking and a safe deposit box are also offered on site.

Sanderling Resort Residences

Save 100% on your flight

$3,201

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) 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.

Four Sails Resort

Northeast Virginia Beach

$492

per person

Oct 22 - Oct 26

found 1 day ago

Roundtrip non-stop flight included

Indianapolis (IND) to Norfolk (ORF)

This condo resort features an indoor pool, a gym, and a restaurant. Enjoy the sauna and perks like free self parking and free WiFi. A picnic area and laundry facilities are also provided.

John Yancey Oceanfront Inn

$696

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) 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.

Top Chesapeake hotels deals

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy, Chesapeake, VA

Free Cancellation

Reserve now, pay when you stay

$59 nightly

$69 total

Aug 24 - Aug 25

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Staff at the 24-hour front desk can provide around-the-clock assistance.

Parking included

Free WiFi

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA

1801 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$128 nightly

$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

1101 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$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

5700 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$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

1900 Pavilion Dr, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$131 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

335 Independence Blvd, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$148 total

Aug 25 - Aug 26

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.

Popular places to visit

Greenbrier Mall

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.

Chesapeake Square Mall

You can find the perfect gifts to bring home at Chesapeake Square Mall during your trip to Chesapeake. Discover the top-notch restaurants and acclaimed theater scene in this family-friendly area.

Chesapeake Conference Center

After visiting Chesapeake Conference Center, make a plan to see the other sights and activities in Chesapeake. Experience the area's great live music and acclaimed theater scene.

Frequently asked questions

How much are vacation packages to Chesapeake?

Travelocity provides package deals to Chesapeake, including flights and hotels, from an impressive $404. With all the extra cash, you could book some cool tours or perhaps even tack on a few extra nights to your getaway.

How long should my Chesapeake vacation be?

There are no strict rules when it comes to how long you should spend in Chesapeake, but most travelers decide to stay around 3 nights. Got some flexibility with your departure date? Consider extending your trip by another night or two. That way, you'll have ample time to check out the area's hidden treasures as well.

Where can I get the best vacation package deals for Chesapeake?

Travelocity is here to help you find an awesome Chesapeake package deal. With no less than 400 partner airlines and 1,000,000 properties worldwide, you're bound to find the perfect mix.

Why should I purchase my Chesapeake vacation bundle with Travelocity?

Nothing beats the feeling of knowing you've bagged the best price in town — that's our Price Match Guarantee. Add to that our impressively broad range of destinations and 24/7 team of customer service professionals and you've got the blueprint for a hassle-free vacation.

Can I save on my Chesapeake car rental if I book it with my hotel or flight?

With a Chesapeake vacation package, you can combine your hotel, flight and car bookings and save a nice amount. If you're eager to see the best of this fabulous city, why not check out Busch Gardens Williamsburg? This well-known sight is 40 mi from Chesapeake. With a rental car, you'll be there in no time.

Which airport is best for Chesapeake?

Many tourists arrive at Norfolk Intl. Airport (ORF). After you've stepped off the plane and grabbed your bags, you'll need to head 10 mi southwest to reach central Chesapeake. Newport News - Williamsburg Intl. Airport (PHF) is another option, 30 mi from the heart of the city.

What is there to do in Chesapeake?

Chesapeake is full of places to discover, such as Chesapeake City Park and Chesapeake City Hall. These well-known attractions are at the top of most people's must-see lists.

Where should I stay when visiting Chesapeake?

Many visitors opt to check in to the Hyatt Place Chesapeake. It's an excellent base for your Chesapeake vacation.