Deals on vacations and trips to Caroline County

Save when you book Caroline County, MD package deals

Choose two or more items and save on your trip:

Caroline County flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel AKA Washington Circle

Hotel AKA Washington Circle

4 out of 5
Downtown Washington D.C.
Price was $847, price is now $608 per person
$608
per person
Apr 22 - Apr 25
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This aparthotel features a restaurant, a gym, and a bar/lounge. WiFi in public areas is free. Valet parking, limo/town car service, and dry cleaning are also offered.
Placemakr Buzzard Point

Placemakr Buzzard Point

2.5 out of 5
Southwest
Save 100% on your flight
Price was $1,047, price is now $710 per person
$710
per person
Apr 25 - May 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A 24-hour gym, self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A communal living room and luggage storage are also provided.
Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Save 100% on your flight
Price was $1,697, price is now $1,213 per person
$1,213
per person
Mar 19 - Mar 22
found 12 hours ago
Roundtrip flight included
Los Angeles (LAX) to Washington (DCA)
The aparthotel's outdoor pool, indoor pool, and 2 bars/lounges are among the featured amenities. Families will appreciate complimentary bicycles and in-room childcare. Enjoy the 24-hour gym and perks like free WiFi.
Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
Price was $1,935, price is now $1,397 per person
$1,397
per person
Mar 18 - Mar 23
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Baltimore (BWI)
This hotel features 2 bars/lounges, a poolside bar, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and airport shuttle. There's a 24-hour gym on site, and laundry facilities and concierge services are also offered.

Top Caroline County hotels deals

Bally's Dover Casino Resort

Bally's Dover Casino Resort

4 out of 5
1131 N Dupont Hwy Dover DE
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $96 total per night
$96 total
Feb 5 - Feb 6
Total with taxes and fees
A casino, 5 restaurants, and a gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at one of the 5 bars/lounges and enjoy perks like free self parking.
Parking included
Free WiFi
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Free Cancellation
Reserve now, pay when you stay
$211 nightly
The price is $240 total per night
$240 total
Feb 9 - Feb 10
Total with taxes and fees
This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's pool. Enjoy the 2 outdoor pools and perks like free self parking and free WiFi.
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3 out of 5
3028 KENT NARROW WAY S Grasonville MD
Free Cancellation
Reserve now, pay when you stay
$133 nightly
The price is $148 total per night
$148 total
Feb 16 - Feb 17
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Pool
Pet friendly
Comfort Inn & Suites Dover near Speedway

Comfort Inn & Suites Dover near Speedway

2.5 out of 5
764 Dover Leipsic Road Dover DE
Free Cancellation
Reserve now, pay when you stay
$86 nightly
The price is $95 total per night
$95 total
Mar 1 - Mar 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Enjoy the hot tub and free perks like buffet breakfast and free self parking. A business center, free WiFi in public areas, and express check-out are also on offer.
Pool
Hot Tub
Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

2 out of 5
1703 E Lebanon Rd Dover DE
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $79 total per night
$79 total
Feb 9 - Feb 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Parking included
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $115 total per night
$115 total
Feb 10 - Feb 11
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Caroline County
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.

Photos of local treasures

Browse Caroline County vacation photos for more inspiration

Aerial view of the Choptank River in Maryland, with calm waters and vibrant greenery
Aerial view of the Choptank River in Maryland, with calm waters and vibrant greenery
Fishing spot
Cute, well cared for, and very uncrowded state park in Maryland. Rent a canoe and paddle up into the creeks that feed the lake for views of abundant plants and wildlife.

Frequently asked questions

How much are vacation packages to Caroline County?
Packages, which provide both flights and hotels in Caroline County, start at just $608. Make your travel dreams come true and secure your trip with Travelocity today.
Where can I get the best vacation package deals for Caroline County?
No matter how you like to travel, Travelocity can help you score an unbeatable Caroline County package deal. The only thing you need to do is select a combination from our 400 airlines and 1,000,000 properties worldwide.
Why should I purchase my Caroline County vacation bundle via Travelocity?
We've got destinations and experiences to suit every type of traveler, top-quality service and 24/7 customer support. To top that off, we'll match any better price you come across with our Price Match Guarantee.
Will I save money on my Caroline County car rental if I combine it with hotels and flights?
Certainly. And our Caroline County vacation packages are the ideal way to do it. In only a few clicks you can save money as well as time by booking everything in one place. Pick up the keys to your rental car then chart your own course. Searching for things to do? Add some activities or experiences to your package and save on those too.
Which airport is best for Caroline County?
Your Caroline County trip will likely start at Baltimore Washington Intl. Thurgood Marshall Airport (BWI) or Salisbury - Ocean City Wicomico Regional Airport (SBY).

Explore More Ways to Travel with Travelocity