Flights To Caroline County - Cheap Flights Starting at

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Kellogg Conference Hotel at Gallaudet University
3.0-star property

Kellogg Conference Hotel at Gallaudet University

Jul 26 - Jul 31

5 night stay

Regina (YQR) to Baltimore (BWI)

Air Canada • Non-stop roundtrip • Coach
Price was CA $1,828, price is now CA $1,323 per person
CA $1,323
per person
found 1 day ago
Sofitel Washington DC Lafayette Square
5.0-star property

Sofitel Washington DC Lafayette Square

Jul 26 - Jul 31

5 night stay

Regina (YQR) to Baltimore (BWI)

Air Canada • Non-stop roundtrip • Coach
Price was CA $2,161, price is now CA $1,541 per person
CA $1,541
per person
found 1 day ago
Kimpton Banneker Hotel by IHG
4.5-star property

Kimpton Banneker Hotel by IHG

Jul 26 - Jul 31

5 night stay

Regina (YQR) to Baltimore (BWI)

Air Canada • Non-stop roundtrip • Coach
Price was CA $1,882, price is now CA $1,373 per person
CA $1,373
per person
found 1 day ago
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Travelers ❤️ These Caroline County 🏨

Bally's Dover Casino Resort

Bally's Dover Casino Resort

4 out of 5
1131 N Dupont Hwy Dover DE
Book a stay at this business-friendly hotel in Dover. Enjoy free WiFi, free parking, and 5 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dover Downs Casino and Dover International Speedway are located nearby.
8.8/10 Excellent! (3,571 reviews)
"There were a lot of food options, but they’re all terrible writing"

Reviewed on May 22, 2026

Opens in a new windowBally's Dover Casino Resort
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dorchester County Historical Society and Bay Country Shop are located nearby.
8.8/10 Excellent! (1,000 reviews)
"Wonderful stay for a long weekend"

Reviewed on May 22, 2026

Opens in a new windowHyatt Regency Chesapeake Bay
Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

2 out of 5
1703 E Lebanon Rd Dover DE
Book a stay at this business-friendly hotel in Dover. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dover Downs Casino and Dover International Speedway are located nearby.
8.2/10 Very Good! (1,005 reviews)
"Waited over 45 minutes to check in, only to be asked to wait even longer so the receptionist could take a PERSONAL phone call… then told a room wasn’t available even though I showed my reservation confirmation, room secured but tried not to offer the same rate & wouldn’t offer any discount for the ..."

Reviewed on May 21, 2026

Opens in a new windowMicrotel Inn & Suites by Wyndham Dover
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Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Chesapeake Bay Maritime Museum and 1879 Hooper Straight Lighthouse are located nearby.
9.6/10 Exceptional! (387 reviews)
"We enjoyed a wonderful, stress-free four days at the inn and the surrounding area. Highly recommend it."

Reviewed on May 22, 2026

Opens in a new windowInn at Perry Cabin
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.

Frequently asked questions

How much is the cheapest flight to Caroline County?
The next trip you take doesn't have to make a huge dent in your finances. In the last seven days, the cheapest roundtrip flight to Caroline County cost . Find a good deal and spend the dollars you save on fantastic experiences. This price was available on Travelocity for flights to Caroline County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Caroline County?
Make sure you leave clear in your calendar, because it's the most affordable month to make your way to Caroline County. That's according to Travelocity's direct flight demand between January and December last year. With more money in your wallet, you can go on a spending spree, go for a fancy meal or do something special.
How can I check my flight status to Caroline County?
Whether you'd like to confirm the status of your flight to Caroline County or make some changes, you'll find all the important info on our handy portal, Trips. Click on "Trips" at the top of our homepage, then sign in or open a new account. Another helpful way to manage and view your booking is with the Travelocity app. Get useful travel alerts right when you need them and share updates with any friends or family flying with you.
How do I find the best deals on flights to Caroline County?
Score an amazing deal with Travelocity — our "Flexible dates" search option makes it a lot easier. Enter the travel dates you want, then click the flexible dates box above your search results to compare prices with the surrounding days. was the most affordable price for a roundtrip flight to Caroline County in the last seven days on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Caroline County with Travelocity?
Where to start! With cheap flights to Caroline County, hotels, rental cars, activities and more, you'll discover all you need for an awesome getaway with Travelocity. Lock in your cheap family flights and take advantage of our round-the-clock customer support and free cancellations on select airlines if you need. Our aim is to offer stress-free travel when you book with us so that you can spend less time on the planning and more time building memories with your travel crew.
How much is a flight to Caroline County on average?
In the last seven days, roundtrip flights to Caroline County were priced between and . No matter your bank balance, we have some amazing deals to help you stick within budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.