Chesapeake Vacation Packages

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Your Chesapeake Vacation

Lock in a Chesapeake vacation package and concentrate on what matters — enjoying yourself. No more planning headaches, just a lot more free time to uncover what's special about this lively city, such as its rich history and family-friendly attractions. Make your trip to Chesapeake even more fun by including some sightseeing. Greenbrier Mall, Oak Grove Lake Park and Chesapeake City Park are among the popular attractions you'll want to explore. Your perfect Chesapeake vacation is just clicks away. Search flights, hotels and more on Expedia for a trip that's tailored just for you.

Top Chesapeake Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Budget Inn Norfolk Va
Buckroe Bungalow Buckroe Bungalow Escape to the Beach 2mins Away
Magnuson Hotel Virginia Beach
The Speakeasy Downtown Newport News
Hampton Inn & Suites Newport News (Oyster Point)

Where to stay in Chesapeake

Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake

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Chesapeake Hotel Deals

Wingate by Wyndham Chesapeake

Wingate by Wyndham Chesapeake

3 out of 5
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from May 17 to May 18
CA $133
CA $156 total
May 17 - May 18
includes taxes & fees
8/10 Very Good! (1,031 reviews)
Breakfast should be at least until 11. In the bathtub, there should be a mat or bathmats inside the bathtub, as the bathtub was extremely slippery.

Reviewed on May 10, 2026

Wingate by Wyndham Chesapeake
STUDIOS & SUITES 4 LESS CHESAPEAKE

STUDIOS & SUITES 4 LESS CHESAPEAKE

2 out of 5
2222 S Military Hwy Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $86 per night from May 28 to May 29
CA $86
CA $102 total
May 28 - May 29
includes taxes & fees
7/10 Good! (799 reviews)
very clean and friendly employee

Reviewed on May 9, 2026

STUDIOS & SUITES 4 LESS CHESAPEAKE
TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
1570 CROSSWAYS BLVD Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from May 17 to May 18
CA $156
CA $185 total
May 17 - May 18
includes taxes & fees
8.6/10 Excellent! (448 reviews)
Everything was great I love the pancake maker

Reviewed on May 9, 2026

TRU by Hilton Chesapeake, VA
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.

What to do in Chesapeake

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.