Chesapeake Holidays
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Where to stay in Chesapeake
Find the best Chesapeake areas and neighborhoods for the activities you enjoy most. Learn more about Chesapeake
Deep Creek South
1 out of top 10 points of interest in this area
While visiting Deep Creek South, you might make a stop by sights like Deep Creek Park and The Crossings at Deep Creek Shopping Center.
Top hotels in Chesapeake
Wingate by Wyndham Chesapeake
817 Greenbrier Circle Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is 2.846.448 ₫ per night from 1 Jun to 2 Jun
2.846.448 ₫
3.326.128 ₫ total
1 Jun - 2 Jun
includes taxes & fees
8/10 Very Good! (1,053 reviews)
"Poor cleaning, dry blood stained covers, the house keeper only took out the trash. The manager was not helpful and not accommodating of us asking for extra towels and actual clean covers and that the housekeeper didn't clean. While not their fault but the elevator was down. No wifi or more power ..."
Reviewed on 25 May 2026
STUDIOS & SUITES 4 LESS CHESAPEAKE
2222 S Military Hwy Chesapeake VA
Fully refundableReserve now, pay when you stay
The price is 1.665.172 ₫ per night from 28 May to 29 May
1.665.172 ₫
1.967.657 ₫ total
28 May - 29 May
includes taxes & fees
7/10 Good! (817 reviews)
"Floor was sticky and ceiling fan box in the bathroom broke. The bed was clean with flat blankets and flat pillows. Basically had my crocs on and stayed in the bed. The room smelled of cigarette smoke even though I asked for a nonsmoking room. Loud people cooking at night but I’m a heavy sleeper so ..."
Reviewed on 23 May 2026
YourSpace Hotels Chesapeake
2137 Starmount Parkway Chesapeake VA
The price is 3.415.738 ₫ per night from 31 May to 1 Jun
3.415.738 ₫
3.980.809 ₫ total
31 May - 1 Jun
includes taxes & fees
9.6/10 Exceptional! (92 reviews)
"Great place for a short stay that had all of the things we needed!"
Reviewed on 25 May 2026
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
You can search for that perfect souvenir 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 search for that perfect souvenir at Chesapeake Square Mall during your visit to Chesapeake. Discover the top-notch restaurants and acclaimed theatre 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 theatre scene and great live music.
