Book Exclusive Chesapeake Vacation Packages
Chesapeake flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Comfort Suites Airport
Central Newport News
per person
Jun. 7 - Jun. 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Book a stay at this beach hotel in Newport News. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bounce House and Patrick Henry Mall are located nearby.
John Yancey Oceanfront Inn
Save 100% on your flight
per person
Jun. 4 - Jun. 10
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Norfolk (ORF)
Book a stay at this beach hotel in Kill Devil Hills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Wright Brothers National Memorial and Destination Fun are located nearby.
The Lodge at Kiln Creek Resort
Central Newport News
per person
Jun. 12 - Jun. 18
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Stay at this 3.5-star golf hotel in Newport News. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Patrick Henry Mall and Hampton Roads Iceplex are located nearby.
Shutters on the Banks
per person
Jun. 4 - Jun. 10
found 5 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Norfolk (ORF)
Stay at this 3.5-star beach hotel in Kill Devil Hills. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Wright Brothers National Memorial and Stop-N-Shop Beach Shop are located nearby.
Comfort Inn & Suites Hampton near Coliseum
Coliseum Central
per person
Jun. 7 - Jun. 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Norfolk (ORF)
Stay at this 3-star business-friendly hotel in Hampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hampton Coliseum and Buckroe Beach and Park are located nearby.
Top Chesapeake hotels deals
Holiday Inn Express Chesapeake - Norfolk by IHG
721 Conference Center Drive, Chesapeake, VA
Free cancellation
The price is CA $131 per night
CA $131
CA $152 total
includes taxes & fees
May 4 - May 5
Stay at this hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Pool
Breakfast included
Wingate by Wyndham Chesapeake
817 Greenbrier Circle, Chesapeake, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $145 per night
CA $145
CA $168 total
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Pool
Hot tub
TRU by Hilton Chesapeake, VA
1570 CROSSWAYS BLVD, Chesapeake, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $139 per night
CA $139
CA $162 total
includes taxes & fees
May 18 - May 19
Stay at this hotel in Chesapeake. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Greenbrier Mall and Waterside District are located nearby.
Breakfast included
Pet-friendly
Wyndham Virginia Beach Oceanfront
5700 Atlantic Ave, Virginia Beach, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $123 per night
CA $123
CA $155 total
includes taxes & fees
May 4 - May 5
Book a stay at this beach hotel in Virginia Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and Virginia Beach Fishing Pier are located nearby.
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 CA $222 per night
CA $222
CA $258 total
includes taxes & fees
May 12 - May 13
Stay at this 3-star beach hotel in Virginia Beach. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Virginia Beach Boardwalk and Virginia Beach Fishing Pier are located nearby.
Pool
Breakfast included
Hilton Virginia Beach Oceanfront
3001 Atlantic Ave, Virginia Beach, VA
Free cancellation
Reserve now, pay when you stay
The price is CA $252 per night
CA $252
CA $294 total
includes taxes & fees
May 26 - May 27
Stay at this 4-star beach resort in Virginia Beach. Enjoy an outdoor pool, a beach locale, and 3 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Virginia Beach Boardwalk and Virginia Beach Fishing Pier are located nearby.
Pool
Free WiFi
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
3.5/5(4 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
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
