![](https://forever.travel-assets.com/flex/flexmanager/images/2020/11/06/TVLY-MSJE-DTG-Hero-Image.jpg?impolicy=fcrop&w=900&h=225&q=mediumHigh)
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.
![Outer Banks Motor Lodge](https://images.trvl-media.com/lodging/14000000/13280000/13278900/13278815/bcd3c70a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
![Sanderling Resort](https://images.trvl-media.com/lodging/1000000/920000/913900/913817/ea67a802_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Sanderling Resort
Save 100% on your flight
per person
Jul 18 - Jul 21
found 1 day ago
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 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.
![Sea Ranch Resort](https://images.trvl-media.com/lodging/2000000/1340000/1336400/1336351/60d8c129_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Sea Ranch Resort
Save 100% on your flight
per person
Jul 26 - Jul 29
found 13 hours ago
Roundtrip non-stop flight included
Cincinnati (CVG) 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.
![Wingate by Wyndham Chesapeake](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/492f9c98_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Wingate by Wyndham Chesapeake
Save 100% on your flight
per person
Aug 24 - Aug 31
found 1 day ago
Roundtrip flight included
Newark (EWR) to Norfolk (ORF)
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.
![John Yancey Oceanfront Inn](https://images.trvl-media.com/lodging/1000000/20000/10700/10663/a961c50d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
John Yancey Oceanfront Inn
Save 100% on your flight
per person
Jul 18 - Jul 21
found 1 day ago
Roundtrip flight included
New York (NYC) 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](https://images.trvl-media.com/lodging/2000000/1520000/1513300/1513238/492f9c98_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Wingate by Wyndham Chesapeake
817 Greenbrier Circle, Chesapeake, VA
Free Cancellation
Reserve now, pay when you stay
The price is $135 per night
$135
per night
Jun 20 - Jun 21
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.
Pool
Hot Tub
![Fairfield Inn and Suites By Marriott Chesapeake](https://images.trvl-media.com/lodging/1000000/20000/16100/16036/w4000h2664x0y0-e0d94c23_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Fairfield Inn and Suites By Marriott Chesapeake
1560 Crossways Blvd, Chesapeake, VA
The price is $125 per night
$125
per night
Jun 30 - Jul 1
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.
Pool
Breakfast included
![Schooner Inn](https://images.trvl-media.com/lodging/2000000/1720000/1711400/1711317/63d70eef_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Schooner Inn
215 Atlantic Ave, Virginia Beach, VA
The price is $190 per night
$190
per night
Jul 8 - Jul 9
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
![Delta Hotels by Marriott Virginia Beach Waterfront](https://images.trvl-media.com/lodging/41000000/40900000/40896500/40896449/edcf023a_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Delta Hotels by Marriott Virginia Beach Waterfront
2800 Shore Drive, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
The price is $329 per night
$329
per night
Jun 19 - Jun 20
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
![Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA](https://images.trvl-media.com/lodging/1000000/10000/5400/5363/bc12dcdb_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
1801 Atlantic Ave, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
The price is $220 per night
$220
per night
Jun 23 - Jun 24
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](https://images.trvl-media.com/lodging/1000000/10000/8200/8175/e69f3e87_y.jpg?impolicy=fcrop&w=420&h=224&q=medium)
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave, Virginia Beach, VA
The price is $159 per night
$159
per night
Jun 23 - Jun 24
This hotel features a restaurant, a seasonal outdoor pool, and a bar/lounge. Guests will appreciate free perks like valet parking and WiFi in public areas. Free self parking, a business center, and a terrace are also offered.
Pool
Pet friendly
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
Browse Chesapeake vacation photos for more inspiration
![Chesapeake Square Mall](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/481000/481121-Chesapeake-Square-Mall.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh)
Frequently asked questions
Top all inclusive vacation packages with airfare
Book a vacation to Chesapeake
Most popular
Hotels
Hotels in LexingtonHotels in DanvilleHotels in FredericksburgHotels in ChincoteagueHotels in WilliamsburgHotels in WinchesterHotels in AlexandriaHotels in Virginia BeachHotels in RoanokeHotels in ManassasHotels in LynchburgHotels in NorfolkHotels in WoodbridgeHotels in BlacksburgHotels in LeesburgHotels in Newport NewsHotels in HamptonBeach Resorts & Hotels in Virginia BeachHotels in Charlottesville
Flights
Cars
Packages