Cheap Vacations in Dorchester County

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Dorchester County vacations

Price found within the past 48 hours. Click for updated prices.
The Georgetown House

The Georgetown House

3 out of 5
Northwest
Save 100% on your flight
Price was $637, price is now $456 per person
$456
per person
Oct 12 - Oct 15
found 1 day 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
Northeast
Save 100% on your flight
Price was $826, price is now $494 per person
$494
per person
Oct 12 - Oct 15
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 $1,604, price is now $997 per person
$997
per person
Oct 2 - Oct 5
found 1 day 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
Downtown Washington D.C.
Save 100% on your flight
Price was $1,750, price is now $1,252 per person
$1,252
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)
Crowne Plaza Dulles Airport by IHG

Crowne Plaza Dulles Airport by IHG

3.5 out of 5
Hutchison
Price was $662, price is now $493 per person
$493
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Inn at Mary's Land Farm

Inn at Mary's Land Farm

3 out of 5
Save 100% on your flight
Price was $857, price is now $649 per person
$649
per person
Oct 9 - Oct 12
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

4 out of 5
Northwest
Save 100% on your flight
Price was $812, price is now $619 per person
$619
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Unit 3 One BR With Queen Sofa and Bed

Unit 3 One BR With Queen Sofa and Bed

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $745, price is now $570 per person
$570
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Northwest
Price was $649, price is now $503 per person
$503
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hyatt Regency Dulles International Airport

Hyatt Regency Dulles International Airport

4 out of 5
McNair
Price was $586, price is now $456 per person
$456
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)

3-night Dorchester County vacations

Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Save 100% on your flight
Price was $658, price is now $417 per person
$417
per person
Oct 15 - Oct 18
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,206, price is now $702 per person
$702
per person
Oct 12 - Oct 15
found 1 day 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
Save 100% on your flight
Price was $826, price is now $494 per person
$494
per person
Oct 12 - Oct 15
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 $1,604, price is now $997 per person
$997
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Willard InterContinental Washington by IHG

Willard InterContinental Washington by IHG

5 out of 5
Save 100% on your flight
Price was $1,678, price is now $1,095 per person
$1,095
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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 $1,346, price is now $916 per person
$916
per person
Oct 12 - Oct 15
found 1 day 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 $835, price is now $573 per person
$573
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Georgetown House

The Georgetown House

3 out of 5
Save 100% on your flight
Price was $637, price is now $456 per person
$456
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

5 out of 5
Save 100% on your flight
Price was $838, price is now $601 per person
$601
per person
Oct 10 - Oct 13
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
Live! Casino & Hotel Maryland

Live! Casino & Hotel Maryland

4.5 out of 5
Save 100% on your flight
Price was $603, price is now $436 per person
$436
per person
Oct 9 - Oct 12
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
The Watergate Hotel

The Watergate Hotel

5 out of 5
Save 100% on your flight
Price was $744, price is now $540 per person
$540
per person
Oct 10 - Oct 13
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
The Hoya Hotel at Georgetown

The Hoya Hotel at Georgetown

2 out of 5
Save 100% on your flight
Price was $734, price is now $535 per person
$535
per person
Oct 12 - Oct 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)

4-night Dorchester County vacations

Price found within the past 48 hours. Click for updated prices.
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Save 100% on your flight
Price was $499, price is now $362 per person
$362
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hotel Hive

Hotel Hive

3.5 out of 5
Save 100% on your flight
Price was $702, price is now $467 per person
$467
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hotel Indigo Old Town Alexandria by IHG

Hotel Indigo Old Town Alexandria by IHG

4 out of 5
Save 100% on your flight
Price was $1,015, price is now $692 per person
$692
per person
Sep 24 - Sep 28
found 16 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Save 100% on your flight
Price was $1,156, price is now $788 per person
$788
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)
Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,000, price is now $709 per person
$709
per person
Oct 8 - Oct 12
found 18 hours ago
Roundtrip flight included
Orlando (MCO) 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 $1,750, price is now $1,252 per person
$1,252
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)
Coda on Half, a Placemakr Experience - Navy Yard

Coda on Half, a Placemakr Experience - Navy Yard

4 out of 5
Save 100% on your flight
Price was $912, price is now $704 per person
$704
per person
Oct 8 - Oct 12
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
Washington Plaza Hotel

Washington Plaza Hotel

4 out of 5
Save 100% on your flight
Price was $1,285, price is now $994 per person
$994
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)
The Watergate Hotel

The Watergate Hotel

5 out of 5
Save 100% on your flight
Price was $908, price is now $705 per person
$705
per person
Sep 24 - Sep 28
found 15 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
Willard InterContinental Washington by IHG

Willard InterContinental Washington by IHG

5 out of 5
Save 100% on your flight
Price was $1,952, price is now $1,519 per person
$1,519
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)
Hotel Washington

Hotel Washington

5 out of 5
Save 100% on your flight
Price was $1,639, price is now $1,277 per person
$1,277
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)
The Westin Crystal City Reagan National Airport

The Westin Crystal City Reagan National Airport

4 out of 5
Save 100% on your flight
Price was $768, price is now $601 per person
$601
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)

5-night Dorchester 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
Save 100% on your flight
Price was $899, price is now $608 per person
$608
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) 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 $1,472, price is now $917 per person
$917
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Save 100% on your flight
Price was $1,170, price is now $822 per person
$822
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
Arlo Washington DC

Arlo Washington DC

4 out of 5
Save 100% on your flight
Price was $1,290, price is now $935 per person
$935
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
citizenM Washington DC Georgetown

citizenM Washington DC Georgetown

4 out of 5
Price was $956, price is now $706 per person
$706
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

4 out of 5
Save 100% on your flight
Price was $1,047, price is now $788 per person
$788
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
Hotel Hive

Hotel Hive

3.5 out of 5
Price was $1,019, price is now $772 per person
$772
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Price was $918, price is now $696 per person
$696
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
citizenM Washington DC Capitol

citizenM Washington DC Capitol

4 out of 5
Save 100% on your flight
Price was $1,097, price is now $836 per person
$836
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
One Washington Circle DC, Tapestry Collection by Hilton

One Washington Circle DC, Tapestry Collection by Hilton

4 out of 5
Price was $1,035, price is now $798 per person
$798
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
citizenM Washington DC NoMa

citizenM Washington DC NoMa

4 out of 5
Price was $960, price is now $753 per person
$753
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)
Sheraton Pentagon City Hotel

Sheraton Pentagon City Hotel

3.5 out of 5
Price was $885, price is now $702 per person
$702
per person
Sep 25 - Sep 30
found 22 hours ago
Roundtrip flight included
Memphis (MEM) to Baltimore (BWI)

6-7 night Dorchester County vacations

Price found within the past 48 hours. Click for updated prices.
Holiday Inn National Airport/Crystal City by IHG

Holiday Inn National Airport/Crystal City by IHG

3.5 out of 5
Save 100% on your flight
Price was $1,080, price is now $698 per person
$698
per person
Oct 16 - Oct 23
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Save 100% on your flight
Price was $1,270, price is now $798 per person
$798
per person
Oct 16 - Oct 22
found 1 hour ago
Roundtrip flight included
Orlando (MCO) 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 $1,615, price is now $1,042 per person
$1,042
per person
Oct 16 - Oct 23
found 16 hours ago
Roundtrip flight included
Orlando (MCO) 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 $1,134, price is now $756 per person
$756
per person
Oct 16 - Oct 22
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
Hotel Washington

Hotel Washington

5 out of 5
Save 100% on your flight
Price was $2,716, price is now $1,859 per person
$1,859
per person
Oct 16 - Oct 23
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
Arlo Washington DC

Arlo Washington DC

4 out of 5
Save 100% on your flight
Price was $1,774, price is now $1,235 per person
$1,235
per person
Oct 16 - Oct 23
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Save 100% on your flight
Price was $1,474, price is now $1,034 per person
$1,034
per person
Oct 16 - Oct 23
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
citizenM Washington DC Georgetown

citizenM Washington DC Georgetown

4 out of 5
Save 100% on your flight
Price was $1,198, price is now $846 per person
$846
per person
Oct 16 - Oct 23
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
Willard InterContinental Washington by IHG

Willard InterContinental Washington by IHG

5 out of 5
Save 100% on your flight
Price was $3,268, price is now $2,321 per person
$2,321
per person
Oct 16 - Oct 23
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
AC Hotel by Marriott Washington DC Capitol Hill Navy Yard

AC Hotel by Marriott Washington DC Capitol Hill Navy Yard

4 out of 5
Save 100% on your flight
Price was $1,561, price is now $1,128 per person
$1,128
per person
Oct 16 - Oct 22
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
The Royal Sonesta Washington DC Capitol Hill

The Royal Sonesta Washington DC Capitol Hill

4.5 out of 5
Save 100% on your flight
Price was $1,499, price is now $1,102 per person
$1,102
per person
Oct 16 - Oct 22
found 1 hour ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)
The Watergate Hotel

The Watergate Hotel

5 out of 5
Save 100% on your flight
Price was $1,698, price is now $1,249 per person
$1,249
per person
Oct 16 - Oct 23
found 16 hours ago
Roundtrip flight included
Orlando (MCO) to Baltimore (BWI)

Top places to visit in Dorchester County

A marina with several boats docked, a building with a sign, and trees in the background.
FlightsFlightsHotelsHotels

Cambridge

Cambridge

Flight deals to Dorchester County

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

Fri, Oct 9 - Mon, Oct 12
BOS
Boston
SBY
Salisbury
$487 Roundtrip, found 1 day ago
$487
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Oct 9 from Boston to Salisbury, returning Mon, Oct 12, priced at $487 found 1 day ago
Sun, Sep 20 - Sun, Sep 27
ATL
Atlanta
SBY
Salisbury
$710 Roundtrip, found 4 days ago
$710
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Sep 20 from Atlanta to Salisbury, returning Sun, Sep 27, priced at $710 found 4 days ago
Thu, Sep 10 - Sun, Sep 13
LGA
New York
SBY
Salisbury
$750 Roundtrip, found 20 hours ago
$750
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Thu, Sep 10 from New York to Salisbury, returning Sun, Sep 13, priced at $750 found 20 hours ago

Top rated hotels for your Dorchester County vacation

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
1.64 mi from city center
$253 nightly
The price is $287 total per night
$287 total
Sep 2 - Sep 3
Total with taxes and fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Eastern Shore Hospital Center.
On private beach
Pool
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
Free Cancellation
Reserve now, pay when you stay
2.35 mi from city center
$81 nightly
The price is $90 total per night
$90 total
Aug 27 - Aug 28
Total with taxes and fees
When you stay at Days Inn & Suites by Wyndham Cambridge in Cambridge, you'll be near the beach, within a 5-minute drive of Bay Country Shop and Meredith House.
Pool
Breakfast included
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
Free Cancellation
2.54 mi from city center
$119 nightly
The price is $133 total per night
$133 total
Aug 30 - Aug 31
Total with taxes and fees
Located in Cambridge, Comfort Inn & Suites Cambridge is within a 10-minute drive of Harriet Tubman Museum and Educational Center and Choptank River Lighthouse.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Dorchester 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.

^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.