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

Inn At The Canal Bed & Breakfast

Inn At The Canal Bed & Breakfast

3.5 out of 5
104 Bohemia Avenue Chesapeake City MD
0.59 km from city center
Book a stay at this business-friendly B&B in Chesapeake City. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Pell Gardens and Chesapeake ...
Sonesta Select Newark Christiana Mall

Sonesta Select Newark Christiana Mall

3 out of 5
48 Geoffrey Dr Newark DE
21.82 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. ...
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 Gallaher ...
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 ...
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 ...
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 ...
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 ...
Comfort Inn & Suites Newark - Wilmington

Comfort Inn & Suites Newark - Wilmington

2.5 out of 5
3 Concord Ln Newark DE
19.22 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 ...
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 ...
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 ...
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 WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the ...
Extended Stay America Suites Newark Christiana Wilmington

Extended Stay America Suites Newark Christiana Wilmington

2.5 out of 5
333 Continental Dr Newark DE
21.23 km from city center
Stay at this hotel in Newark. Enjoy free breakfast, free WiFi, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
Red Roof Inn & Suites Wilmington - New Castle

Red Roof Inn & Suites Wilmington - New Castle

2 out of 5
1612 North DuPont Highway New Castle DE
27.65 km from city center
Book a stay at this business-friendly hotel in New Castle. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Wilmington Riverwalk ...
Holiday Inn Express & Suites Wilmington-Newark by IHG

Holiday Inn Express & Suites Wilmington-Newark by IHG

2.5 out of 5
1201 Christiana Rd Newark DE
19.33 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 ...
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 ...
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, Dec 17 - Thu, Jan 1
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 1 day ago
$60
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Dec 17 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Jan 1, priced at $60 found 1 day ago
Spirit Airlines
Tue, Jan 13 - Sat, Jan 31
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Jan 31, priced at $70 found 1 day ago
Delta
Tue, Jan 20 - Sat, Feb 7
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$217 Roundtrip, found 6 days ago
$217
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jan 20 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, Feb 7, priced at $217 found 6 days ago
American Airlines
Tue, Dec 16 - Tue, Jan 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$261 Roundtrip, found 1 day ago
$261
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 16 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Jan 6, priced at $261 found 1 day ago
United
Thu, Dec 25 - Thu, Jan 8
DEN
Denver Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$321 Roundtrip, found 1 day ago
$321
Roundtrip
found 1 day ago
Select United flight, departing Thu, Dec 25 from Denver Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Thu, Jan 8, priced at $321 found 1 day ago