Chesapeake Vacation Packages 2025/2026 from $439

Chesapeake flight + hotel vacation packages

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

Sea Ranch Resort

Save 100% on your flight

$439

per person

Oct 14 - Oct 21

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference center. Enjoy the gym and perks like free self parking.

Boardwalk Resort and Villas

Northeast Virginia Beach

Save 100% on your flight

$595

per person

Oct 14 - Oct 21

found 7 hours ago

Roundtrip flight included

Boston (BOS) 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.

Sea Scape Beach and Golf Villas

Sea Scape

Save 100% on your flight

$612

per person

Oct 14 - Oct 21

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

2 outdoor pools, an indoor pool, and an outdoor tennis court are all featured at this smoke-free condo. Bring the family and enjoy the mini golf, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.

Outer Banks Beach Club

Save 100% on your flight

$527

per person

Oct 14 - Oct 21

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

2 outdoor pools, 3 hot tubs, and an indoor pool are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Guests will appreciate free perks like free self parking and WiFi in public areas.

The Burrus House Inn Waterfront Suites

Save 100% on your flight

$1,736

per person

Oct 14 - Oct 21

found 7 hours ago

Roundtrip flight included

Boston (BOS) to Norfolk (ORF)

This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A snack bar/deli, express check-in, and express check-out are also on offer.

Top Chesapeake hotels deals

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd, Chesapeake, VA

Free Cancellation

Reserve now, pay when you stay

$80 nightly

$94 total

Oct 5 - Oct 6

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and free internet in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Pool

Breakfast included

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy, Chesapeake, VA

Free Cancellation

Reserve now, pay when you stay

$59 nightly

$69 total

Sep 8 - Sep 9

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

Schooner Inn

215 Atlantic Ave, Virginia Beach, VA

$80 nightly

$94 total

Oct 1 - Oct 2

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

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

1801 Atlantic Ave, Virginia Beach, VA

Free Cancellation

$114 nightly

$134 total

Sep 28 - Sep 29

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, an Ascend Collection Hotel

1101 Atlantic Ave, Virginia Beach, VA

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$99 total

Oct 5 - Oct 6

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

Holiday Inn & Suites Virginia Beach North Beach by IHG

3900 Atlantic Avenue, Virginia Beach, VA

Free Cancellation

$143 nightly

$166 total

Sep 28 - Sep 29

Total with taxes and fees

This smoke-free hotel features 3 restaurants, 3 outdoor pools, and an indoor pool. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's fun for all ages with a lazy river and a free kid's club, and families will appreciate the onsite laundry facilities.

Pool

Hot Tub

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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 $439. 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.