
Deals on vacations and trips to Chesapeake
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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
Aug 15 - Aug 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
Aug 15 - Aug 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.

John Yancey Oceanfront Inn
Save 100% on your flight
per person
Aug 15 - Aug 19
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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.


Four Sails Resort
Northeast Virginia Beach
Save 100% on your flight
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
New York (JFK) 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.
Top Chesapeake hotels deals

Holiday Inn & Suites Virginia Beach North Beach by IHG
3900 Atlantic Avenue, Virginia Beach, VA
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

Country Inn & Suites by Radisson, Virginia Beach (Oceanfront), VA
1801 Atlantic Ave, Virginia Beach, VA
Free Cancellation
Reserve now, pay when you stay
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
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
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

Aqua Vista Resort Hotel
1719 Atlantic Ave, Virginia Beach, VA
Free Cancellation
A seasonal outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
Pool
Parking 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 acclaimed theater scene and great live music.
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Top all inclusive vacation packages with airfare
- Flights to Norfolk - Virginia Beach
- Visit Chesapeake Central Library
- Flights to Portsmouth
- Hotels near Greenbrier Mall
- Visit Commodore Theatre
- Visit Portsmouth Naval Shipyard Museum
- Hotels in Portsmouth
- Hotels in Norfolk
- Cheap Hotels in Portsmouth
- Oceanfront Hotels in Virginia Beach
- Car rentals in Portsmouth
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