Chesapeake City Vacations

Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*

Choose two or more items and save on your trip:

Top Hotel Deals

Quality Inn Newark - Wilmington

Quality Inn Newark - Wilmington

2.5 out of 5
65 Geoffrey Dr Newark DE
21.8 km from city center
Book a stay at this business-friendly hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Christiana Mall and Hale-Byrnes ...
Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr Newark DE
21.78 km from city center
Stay at this hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Great Wolf Lodge Perryville

Great Wolf Lodge Perryville

2 out of 5
1240 Chesapeke Overlook Parkway Perryville MD
23.77 km from city center
Stay at this hotel in Perryville. Enjoy free WiFi, 4 restaurants, and water park access (surcharge). Popular attractions Hollywood Casino and Garrett Island ...
Embassy Suites by Hilton Newark Wilmington South

Embassy Suites by Hilton Newark Wilmington South

3.5 out of 5
654 S College Ave Newark DE
15.03 km from city center
Book a stay at this business-friendly hotel in Newark. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Sonesta ES Suites Wilmington - Newark

Sonesta ES Suites Wilmington - Newark

3 out of 5
240 Chapman Rd Newark DE
18.57 km from city center
Stay at this hotel in Newark. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
Red Roof Inn & Suites Newark - University

Red Roof Inn & Suites Newark - University

2 out of 5
1119 S College Avenue Newark DE
14.18 km from city center
Stay at this hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
Best Western Plus Newark/Christiana Inn

Best Western Plus Newark/Christiana Inn

2.5 out of 5
875 Pulaski Highway Bear DE
17.99 km from city center
Book a stay at this business-friendly hotel in Bear. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Woodspring Suites Wilmington Riverfront

Woodspring Suites Wilmington Riverfront

2.5 out of 5
600 A Street Wilmington DE
31.5 km from city center
Stay at this hotel in Wilmington. Enjoy free WiFi, free parking, and a 24-hour fitness center. Popular attractions Tubman-Garrett Riverfront Park and Christina ...
Red Roof Inn PLUS+ Wilmington - Newark

Red Roof Inn PLUS+ Wilmington - Newark

2.5 out of 5
415 Stanton Christiana Road Newark DE
22.03 km from city center
Stay at this hotel in Newark. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Ramada by Wyndham Newark/Wilmington

Ramada by Wyndham Newark/Wilmington

3 out of 5
280 Chapman Rd Newark DE
19.14 km from city center
Book a stay at this business-friendly hotel in Newark. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Baymont by Wyndham Newark at University of Delaware

Baymont by Wyndham Newark at University of Delaware

2.5 out of 5
630 S College Ave Newark DE
15.1 km from city center
Book a stay at this business-friendly hotel in Newark. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
Hilton Wilmington/Christiana

Hilton Wilmington/Christiana

4 out of 5
100 Continental Dr Newark DE
21.62 km from city center
Book a stay at this business-friendly hotel in Newark. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hyatt Place Wilmington Riverfront

Hyatt Place Wilmington Riverfront

3 out of 5
760 Justison Street Wilmington DE
30.72 km from city center
Book a stay at this business-friendly hotel in Wilmington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Red Roof Inn Perryville

Red Roof Inn Perryville

2 out of 5
61 Heather Lane Perryville MD
23.17 km from city center
Book a stay at this business-friendly inn in Perryville. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Hollywood Casino and Garrett ...
Motel 6 Newark, DE

Motel 6 Newark, DE

2 out of 5
100 Mcintosh Plaza Newark DE
19.31 km from city center
Stay at this motel in Newark. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Christiana Mall and Christiana Skating Center are ...
Don't see what you're looking for?
See all available properties in Chesapeake City
View all properties
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.

Top Flight Deals

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Wed, Aug 12 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$76 Roundtrip, found 17 hours ago
$76
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Aug 25, priced at $76 found 17 hours ago
Southwest Airlines
Tue, Aug 11 - Wed, Aug 12
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$143 Roundtrip, found 6 hours ago
$143
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Tue, Aug 11 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Aug 12, priced at $143 found 6 hours ago
Delta
Tue, Jul 7 - Tue, Jul 14
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Delta flight, departing Tue, Jul 7 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 14, priced at $157 just found
JetBlue Airways
Fri, Jul 24 - Mon, Jul 27
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$207 Roundtrip, found 23 hours ago
$207
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Fri, Jul 24 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Jul 27, priced at $207 found 23 hours ago
American Airlines
Tue, Jul 21 - Tue, Jul 28
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$209 Roundtrip, found 3 days ago
$209
Roundtrip
found 3 days ago
Select American Airlines flight, departing Tue, Jul 21 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jul 28, priced at $209 found 3 days ago