Cheap Vacations in Caroline County

Choose two or more items and save on your trip:

Caroline County vacations

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was $491, price is now $380 per person
$380
per person
Nov 19 - Nov 22
found 15 hours ago
Roundtrip flight included
Minneapolis (MSP) to Baltimore (BWI)
Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
Save 100% on your flight
Price was $1,701, price is now $1,062 per person
$1,062
per person
Nov 25 - Nov 29
found 16 hours ago
Roundtrip flight included
St. Louis (STL) to Baltimore (BWI)
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Save 100% on your flight
Price was $1,621, price is now $1,091 per person
$1,091
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was $848, price is now $575 per person
$575
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $1,418, price is now $996 per person
$996
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,076, price is now $770 per person
$770
per person
Nov 21 - Nov 25
found 17 hours ago
Roundtrip flight included
St. Louis (STL) to Baltimore (BWI)
Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $1,175, price is now $856 per person
$856
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was $994, price is now $755 per person
$755
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Price was $1,112, price is now $854 per person
$854
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hyatt Regency Washington on Capitol Hill

Hyatt Regency Washington on Capitol Hill

4 out of 5
Northwest
Price was $1,091, price is now $841 per person
$841
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)

3-night Caroline County vacations

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Price was $368, price is now $298 per person
$298
per person
Nov 19 - Nov 22
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Price was $491, price is now $380 per person
$380
per person
Nov 19 - Nov 22
found 15 hours ago
Roundtrip flight included
Minneapolis (MSP) to Baltimore (BWI)
Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Price was $481, price is now $373 per person
$373
per person
Nov 19 - Nov 22
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Waypoint

The Waypoint

2 out of 5
Price was $514, price is now $398 per person
$398
per person
Nov 20 - Nov 23
found 17 hours ago
Roundtrip flight included
Minneapolis (MSP) to Baltimore (BWI)
Beach Walk

Beach Walk

2 out of 5
Price was $2,311, price is now $1,808 per person
$1,808
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Price was $436, price is now $342 per person
$342
per person
Nov 19 - Nov 22
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
citizenM Washington DC Georgetown

citizenM Washington DC Georgetown

4 out of 5
Price was $486, price is now $391 per person
$391
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Sheraton Baltimore North Hotel

Sheraton Baltimore North Hotel

3.5 out of 5
Price was $550, price is now $444 per person
$444
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)
citizenM Washington DC NoMa

citizenM Washington DC NoMa

4 out of 5
Price was $502, price is now $410 per person
$410
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
YOTEL Washington DC, Select by Hilton

YOTEL Washington DC, Select by Hilton

4 out of 5
Price was $427, price is now $352 per person
$352
per person
Nov 19 - Nov 22
found 16 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Residence Inn by Marriott Alexandria Old Town South at Carlyle

Residence Inn by Marriott Alexandria Old Town South at Carlyle

3 out of 5
Price was $500, price is now $419 per person
$419
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Convention center Indoor free parking

Convention center Indoor free parking

4 out of 5
Price was $510, price is now $430 per person
$430
per person
Nov 25 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)

4-night Caroline County vacations

Price found within the past 48 hours. Click for updated prices.
citizenM Washington DC NoMa

citizenM Washington DC NoMa

4 out of 5
Price was $657, price is now $497 per person
$497
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland

5 out of 5
Save 100% on your flight
Price was $1,701, price is now $1,062 per person
$1,062
per person
Nov 25 - Nov 29
found 16 hours ago
Roundtrip flight included
St. Louis (STL) to Baltimore (BWI)
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Save 100% on your flight
Price was $884, price is now $558 per person
$558
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Price was $848, price is now $575 per person
$575
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Potomac Hotel, Autograph Collection

The Potomac Hotel, Autograph Collection

5 out of 5
Save 100% on your flight
Price was $1,724, price is now $1,174 per person
$1,174
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Save 100% on your flight
Price was $1,687, price is now $1,170 per person
$1,170
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Graham Georgetown

The Graham Georgetown

4 out of 5
Save 100% on your flight
Price was $1,418, price is now $996 per person
$996
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Eaton DC

Eaton DC

4.5 out of 5
Price was $878, price is now $621 per person
$621
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hotel Burg

Hotel Burg

4 out of 5
Save 100% on your flight
Price was $1,076, price is now $770 per person
$770
per person
Nov 21 - Nov 25
found 17 hours ago
Roundtrip flight included
St. Louis (STL) to Baltimore (BWI)
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

3 out of 5
Price was $892, price is now $642 per person
$642
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Holiday Inn National Airport/Crystal City by IHG

Holiday Inn National Airport/Crystal City by IHG

3.5 out of 5
Price was $749, price is now $547 per person
$547
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Arlo Washington DC

Arlo Washington DC

4 out of 5
Price was $769, price is now $584 per person
$584
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)

6-7 night Caroline County vacations

Price found within the past 48 hours. Click for updated prices.
citizenM Washington DC NoMa

citizenM Washington DC NoMa

4 out of 5
Price was $900, price is now $619 per person
$619
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,242, price is now $702 per person
$702
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Save 100% on your flight
Price was $2,214, price is now $1,358 per person
$1,358
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

3 out of 5
Save 100% on your flight
Price was $1,259, price is now $820 per person
$820
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Graham Georgetown

The Graham Georgetown

4 out of 5
Save 100% on your flight
Price was $1,967, price is now $1,325 per person
$1,325
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Save 100% on your flight
Price was $1,621, price is now $1,091 per person
$1,091
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
citizenM Washington DC Georgetown

citizenM Washington DC Georgetown

4 out of 5
Price was $951, price is now $674 per person
$674
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Watergate Hotel

The Watergate Hotel

5 out of 5
Save 100% on your flight
Price was $1,550, price is now $1,106 per person
$1,106
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Arlo Washington DC

Arlo Washington DC

4 out of 5
Save 100% on your flight
Price was $1,059, price is now $758 per person
$758
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

4 out of 5
Save 100% on your flight
Price was $1,175, price is now $856 per person
$856
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Holiday Inn Express Washington DC Downtown by IHG

Holiday Inn Express Washington DC Downtown by IHG

2.5 out of 5
Price was $871, price is now $651 per person
$651
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hotel Hive

Hotel Hive

3.5 out of 5
Price was $934, price is now $698 per person
$698
per person
Dec 7 - Dec 14
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)

Top places to visit in Caroline County

A calm lake surrounded by tall trees and dense reeds.
FlightsFlightsHotelsHotels

Denton

Denton
A forest with tall trees and a sunset in the background.
FlightsFlightsHotelsHotels

Ridgely

Ridgely

Flight deals to Caroline County

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Nov 6 - Sun, Nov 8
SJU
San Juan
SBY
Salisbury
$356 Roundtrip, found 3 days ago
$356
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Nov 6 from San Juan to Salisbury, returning Sun, Nov 8, priced at $356 found 3 days ago
Fri, Nov 6 - Sun, Nov 8
SJU
San Juan
SBY
Salisbury
$364 Roundtrip, found 6 days ago
$364
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, Nov 6 from San Juan to Salisbury, returning Sun, Nov 8, priced at $364 found 6 days ago
Fri, Nov 6 - Sun, Nov 8
SJU
San Juan
SBY
Salisbury
$373 Roundtrip, found 4 days ago
$373
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Nov 6 from San Juan to Salisbury, returning Sun, Nov 8, priced at $373 found 4 days ago

Top rated hotels for your Caroline County vacation

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
26.25 mi from city center
$110 nightly
The price is $120 total per night
$120 total
Oct 21 - Oct 22
Total with taxes and fees
With a stay at Bally's Dover Casino Resort in Dover, you'll be just steps from Dover Downs Casino and 7 minutes by foot from Dover International Speedway.
Parking included
Free WiFi
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
21.94 mi from city center
$89 nightly
The price is $98 total per night
$98 total
Nov 1 - Nov 2
Total with taxes and fees
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime Museum.
Pool
Breakfast included
Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

2 out of 5
22297 Dupont Blvd Georgetown DE
Free Cancellation
Reserve now, pay when you stay
27.28 mi from city center
$84 nightly
The price is $93 total per night
$93 total
Oct 25 - Oct 26
Total with taxes and fees
A stay at Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches places you in the heart of Georgetown, within a 5-minute drive of Delaware Technical Community College Georgetown Campus and Georgetown Circle.
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.