
Deals on vacations and trips to Chesapeake
Save when you book Chesapeake package deals
Chesapeake flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.

Sea Ranch Resort
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop 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.

Ocean Pines Resort
Save 100% on your flight
per person
Jul 10 - Jul 17
found 1 day ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
This vacation home features an indoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Guests will appreciate free perks like free self parking and WiFi in public areas.

Four Sails Resort
Northeast Virginia Beach
Save 100% on your flight
per person
Jun 16 - Jun 20
found 16 hours ago
Roundtrip flight included
New York (NYC) 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
Save 100% on your flight
per person
Jun 8 - Jun 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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

Wingate by Wyndham Chesapeake
817 Greenbrier Circle, Chesapeake, VA
Free Cancellation
Reserve now, pay when you stay
The price is $126 per night
$126
includes taxes & fees
$109 per night
May 26 - May 27
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 hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub

TRU by Hilton Chesapeake, VA
1570 CROSSWAYS BLVD, Chesapeake, VA
Free Cancellation
Reserve now, pay when you stay
The price is $117 per night
$117
includes taxes & fees
$101 per night
May 11 - May 12
A gym is featured at this hotel, along with free self parking. Guests will appreciate free perks like buffet breakfast and WiFi in public areas. A 24-hour business center, express check-in, and express check-out are also on offer.
Breakfast included
Pet friendly

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
1801 Atlantic Ave, Virginia Beach, VA
Free Cancellation
The price is $139 per night
$139
includes taxes & fees
$119 per night
May 7 - May 8
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. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Pool
Breakfast included

Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
The price is $112 per night
$112
includes taxes & fees
$96 per night
May 5 - May 6
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

Delta Hotels by Marriott Virginia Beach Waterfront
2800 Shore Drive, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
The price is $131 per night
$131
includes taxes & fees
$112 per night
May 28 - May 29
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

Hyatt Place Virginia Beach / Oceanfront
3601 ATLANTIC AVENUE, 36TH AND ATLANTIC, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
The price is $187 per night
$187
includes taxes & fees
$161 per night
May 11 - May 12
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 free buffet breakfast each morning.
Pool
Breakfast included
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
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.

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 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.
Photos of local treasures
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