Deals on vacations and trips to Caroline County

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Caroline County flight + hotel vacation packages

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

Hotel Washington

5 out of 5
Downtown Washington D.C.
Price was $495, price is now $346 per person
$346
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. A terrace, a snack bar/deli, and luggage storage are also on offer.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $582, price is now $400 per person
$400
per person
Mar 13 - Mar 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.
West End Washington DC, Tapestry Collection by Hilton

West End Washington DC, Tapestry Collection by Hilton

3 out of 5
Downtown Washington D.C.
Price was $735, price is now $528 per person
$528
per person
Apr 19 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. Self parking, a lobby fireplace, and express check-in are also offered.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
Price was $1,025, price is now $749 per person
$749
per person
Apr 19 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
This smoke-free hotel features a full-service spa, a marina, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free area shuttle.
The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Save 100% on your flight
Price was $790, price is now $589 per person
$589
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. Make the most of the gym and a rooftop terrace, and relax with drinks at one of the 3 bars/lounges.

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 4 - Feb 5
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.
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.
On private beach
Pool
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.
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 5 - Feb 6
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
$103 nightly
The price is $114 total per night
$114 total
Feb 16 - Feb 17
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
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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 $346. 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).

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