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)
Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
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
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 $1,346, 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)
Hotel Indigo Old Town Alexandria by IHG

Hotel Indigo Old Town Alexandria by IHG

4 out of 5
Old Town Alexandria
Save 100% on your flight
Price was $1,015, price is now $692 per person
$692
per person
Sep 24 - Sep 28
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
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)
Hotel Washington

Hotel Washington

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $998, price is now $717 per person
$717
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Hoya Hotel at Georgetown

The Hoya Hotel at Georgetown

2 out of 5
Northwest
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)
Placemakr Dupont Circle

Placemakr Dupont Circle

4 out of 5
Northwest
Save 100% on your flight
Price was $1,335, price is now $981 per person
$981
per person
Sep 24 - Sep 28
found 1 hour 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 23 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 1 day ago
Roundtrip flight included
Tampa (TPA) 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 1 day 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)
The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Save 100% on your flight
Price was $1,273, price is now $929 per person
$929
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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)
The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Save 100% on your flight
Price was $847, price is now $571 per person
$571
per person
Oct 10 - Oct 14
found 6 hours 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 24 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Save 100% on your flight
Price was $1,001, price is now $695 per person
$695
per person
Oct 3 - Oct 7
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 $1,108, price is now $795 per person
$795
per person
Oct 10 - Oct 14
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hotel Washington

Hotel Washington

5 out of 5
Save 100% on your flight
Price was $998, price is now $717 per person
$717
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Capitol Hill Hotel

Capitol Hill Hotel

4 out of 5
Save 100% on your flight
Price was $763, price is now $559 per person
$559
per person
Oct 5 - Oct 9
found 1 hour 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 $786, price is now $577 per person
$577
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Placemakr Dupont Circle

Placemakr Dupont Circle

4 out of 5
Save 100% on your flight
Price was $1,335, price is now $981 per person
$981
per person
Sep 24 - Sep 28
found 1 hour 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 $1,168, price is now $861 per person
$861
per person
Oct 10 - Oct 14
found 6 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 $675, price is now $497 per person
$497
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.
Hyatt Place Baltimore/BWI Airport

Hyatt Place Baltimore/BWI Airport

3 out of 5
Save 100% on your flight
Price was $458, price is now $340 per person
$340
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Live! Casino & Hotel Maryland

Live! Casino & Hotel Maryland

4.5 out of 5
Save 100% on your flight
Price was $886, price is now $623 per person
$623
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Hotel Indigo Baltimore Downtown by IHG

Hotel Indigo Baltimore Downtown by IHG

4 out of 5
Save 100% on your flight
Price was $663, price is now $478 per person
$478
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Save 100% on your flight
Price was $783, price is now $568 per person
$568
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

3.5 out of 5
Save 100% on your flight
Price was $591, price is now $462 per person
$462
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

Kimpton Hotel Monaco Baltimore Inner Harbor by IHG

4.5 out of 5
Save 100% on your flight
Price was $731, price is now $576 per person
$576
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Holiday Inn Baltimore BWI Airport by IHG

Holiday Inn Baltimore BWI Airport by IHG

3 out of 5
Save 100% on your flight
Price was $498, price is now $393 per person
$393
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
The Royal Sonesta Harbor Court Baltimore

The Royal Sonesta Harbor Court Baltimore

4.5 out of 5
Save 100% on your flight
Price was $640, price is now $510 per person
$510
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Hyatt Place Baltimore Inner Harbor

Hyatt Place Baltimore Inner Harbor

3.5 out of 5
Save 100% on your flight
Price was $674, price is now $540 per person
$540
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Courtyard by Marriott Baltimore BWI Airport

Courtyard by Marriott Baltimore BWI Airport

3 out of 5
Save 100% on your flight
Price was $593, price is now $481 per person
$481
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
The Westin Baltimore Washington Airport - BWI

The Westin Baltimore Washington Airport - BWI

4 out of 5
Price was $496, price is now $406 per person
$406
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)
Aloft by Marriott Arundel Mills BWI Airport

Aloft by Marriott Arundel Mills BWI Airport

3 out of 5
Price was $472, price is now $389 per person
$389
per person
Sep 24 - Sep 29
found 3 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Baltimore (BWI)

6-7 night Dorchester County vacations

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

citizenM Washington DC Georgetown

4 out of 5
Save 100% on your flight
Price was $1,115, price is now $802 per person
$802
per person
Oct 17 - Oct 24
found 10 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 $1,648, price is now $1,006 per person
$1,006
per person
Oct 17 - Oct 24
found 10 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 $2,262, price is now $1,393 per person
$1,393
per person
Oct 17 - Oct 24
found 10 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
Save 100% on your flight
Price was $1,340, price is now $905 per person
$905
per person
Oct 17 - Oct 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Save 100% on your flight
Price was $1,222, price is now $837 per person
$837
per person
Oct 17 - Oct 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Hotel Washington

Hotel Washington

5 out of 5
Save 100% on your flight
Price was $2,575, price is now $1,812 per person
$1,812
per person
Oct 17 - Oct 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) 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 $1,656, price is now $1,193 per person
$1,193
per person
Oct 17 - Oct 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
One Washington Circle DC, Tapestry Collection by Hilton

One Washington Circle DC, Tapestry Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $1,265, price is now $913 per person
$913
per person
Oct 17 - Oct 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Save 100% on your flight
Price was $1,130, price is now $827 per person
$827
per person
Oct 17 - Oct 24
found 10 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 $1,652, price is now $1,243 per person
$1,243
per person
Oct 17 - Oct 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
citizenM Washington DC Capitol

citizenM Washington DC Capitol

4 out of 5
Save 100% on your flight
Price was $1,203, price is now $920 per person
$920
per person
Oct 17 - Oct 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Save 100% on your flight
Price was $1,442, price is now $1,108 per person
$1,108
per person
Oct 17 - Oct 24
found 10 hours ago
Roundtrip flight included
Boston (BOS) 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 2 days ago
$487
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Oct 9 from Boston to Salisbury, returning Mon, Oct 12, priced at $487 found 2 days ago
Sun, Sep 20 - Sun, Sep 27
ATL
Atlanta
SBY
Salisbury
$710 Roundtrip, found 5 days ago
$710
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sun, Sep 20 from Atlanta to Salisbury, returning Sun, Sep 27, priced at $710 found 5 days ago
Thu, Sep 10 - Sun, Sep 13
LGA
New York
SBY
Salisbury
$750 Roundtrip, found 1 day ago
$750
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Sep 10 from New York to Salisbury, returning Sun, Sep 13, priced at $750 found 1 day 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.
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
$120 nightly
The price is $133 total per night
$133 total
Aug 31 - Sep 1
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.