Deals on vacations and trips to Chesapeake

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Chesapeake flight + hotel vacation packages

Sanderling Resort

Sanderling Resort

4 out of 5
Save 100% on your flight
per person
May 23 - May 28
Roundtrip flight included
New York (JFK) 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. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.
Turtle Cay Resort

Turtle Cay Resort

2.5 out of 5
Northeast Virginia Beach
per person
May 22 - May 25
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
2 outdoor pools, 2 spa tubs, and a gym are all featured at this smoke-free hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A business center, a terrace, and a lobby fireplace are also on offer.
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
per person
May 22 - May 25
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
This hotel features an indoor pool and a gym. There's fun for all ages with a children's pool and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the outdoor tennis court and perks like free WiFi.
Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
per person
May 22 - May 25
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
This hotel features an indoor pool and a gym. Enjoy the spa tub and perks like free self parking and free WiFi. A business center, express check-out, and laundry facilities are also on offer.
Ocean 27

Ocean 27

2.5 out of 5
Northeast Virginia Beach
per person
May 22 - May 25
Roundtrip flight included
New York (JFK) to Norfolk (ORF)
A seasonal outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace and luggage storage are also provided.
Prices and availability subject to change. Additional terms may apply.

Top Chesapeake hotels deals

Comfort Suites Chesapeake - Norfolk

Comfort Suites Chesapeake - Norfolk

2.5 out of 5
1550 Crossways Blvd, Chesapeake, VA
Free Cancellation
Reserve now, pay when you stay
The price is $93 per night
$93
per night
May 5 - May 6
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.
Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

2.5 out of 5
817 Greenbrier Circle, Chesapeake, VA
Free Cancellation
Reserve now, pay when you stay
The price is $127 per night
$127
per night
Apr 21 - Apr 22
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the spa tub and free perks like continental breakfast and free self parking.
Fairfield Inn and Suites By Marriott Chesapeake

Fairfield Inn and Suites By Marriott Chesapeake

2.5 out of 5
1560 Crossways Blvd, Chesapeake, VA
Free Cancellation
Reserve now, pay when you stay
The price is $98 per night
$98
per night
Apr 28 - Apr 29
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Delta Hotels by Marriott Virginia Beach Waterfront

Delta Hotels by Marriott Virginia Beach Waterfront

4 out of 5
2800 Shore Drive, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
The price is $144 per night
$144
per night
Apr 21 - Apr 22
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.
Schooner Inn

Schooner Inn

2 out of 5
215 Atlantic Ave, Virginia Beach, VA
The price is $140 per night
$140
per night
May 6 - May 7
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.
Costa Azul Suites Virginia Beach by Red Collection

Costa Azul Suites Virginia Beach by Red Collection

2.5 out of 5
2604 Atlantic Avenue, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
The price is $73 per night
$73
per night
Apr 23 - Apr 24
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
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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

Image for Greenbrier Mall

Greenbrier Mall

4/5(260 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.

Greenbrier Mall
Image for Chesapeake Square Mall

Chesapeake Square Mall

4/5(76 reviews)

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 Square Mall
Image for Chesapeake Conference Center

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.

Chesapeake Conference Center

Frequently asked questions

How much are vacation packages to Chesapeake?
With vacation packages available for just $374, you won’t need to max out the credit card for your visit to Chesapeake. Travelocity is here to help. Bundle your flights, hotels and tours into a convenient package and score some serious discounts. The more you book, the bigger the savings.
How long should my Chesapeake vacation be?
There are no firm rules when it comes to how long you should spend in Chesapeake, but the majority of people opt to stay for around 2 nights. Got some wiggle room in your travel dates? Extend your vacation by a couple more nights. Then you’ll have plenty of time to check out the area’s off-the-beaten-path gems as well.
Where can I get the best vacation package deals for Chesapeake?
Check out Travelocity. With access to 400 airlines and a massive 1,000,000 worldwide properties, creating the perfect Chesapeake package deal couldn’t be simpler.
Why should I purchase my Chesapeake vacation bundle via Travelocity?
Because we believe in crafting stress-free vacation experiences. From flights and hotels to car rentals and activities, our packages make traveling a breeze. Our customer support team is on hand 24/7 to ensure you’ll never roam alone. We also have a Price Match Guarantee, so you can secure your getaway knowing you’ve landed the best deal around. If you find a lower price, we’ll match it!
Will I save money on my Chesapeake car rental if I combine it with hotels and flights?
Certainly — combine your flight, car and hotel into a Chesapeake vacation package and you can save a ton. With so much to see and do in Chesapeake, that set of wheels will make exploring a joy. Once you’re in the driver’s seat, crank up the tunes and make your way to Busch Gardens Williamsburg, a must-see sight about 40 mi from Chesapeake.
What is the best time of year to go to Chesapeake?
Consider visiting in March, May and August if you want to be in the thick of the action. While they’re the busiest months of the year, the buzzing energy that comes with the peak period is tough to resist. If you’re chasing a calmer pace, December, January and February will fit your plans better. Don’t want to pay big bucks for your digs? Avoid booking a room in , when prices skyrocket. Search for someplace more affordable in instead.
Which airport is best for Chesapeake?
One of your best options is Norfolk Intl. Airport (ORF), roughly 10 mi northeast of the hustle and bustle of downtown Chesapeake. You also have Newport News - Williamsburg Intl. Airport (PHF), 30 mi away from central Chesapeake).
What is there to do in Chesapeake?
Chesapeake is full of places to explore, including Greenbrier Mall and Chesapeake Square Mall. These renowned attractions top most people’s travel itineraries.
Where should I stay when visiting Chesapeake?
The Hyatt Place Chesapeake is recommended by many travelers. Book soon to avoid missing out.