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)
Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Save 100% on your flight
Price was $1,046, price is now $630 per person
$630
per person
Oct 20 - Oct 22
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)
Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Save 100% on your flight
Price was $823, price is now $569 per person
$569
per person
Oct 20 - Oct 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
Residence Inn by Marriott Washington, DC National Mall

Residence Inn by Marriott Washington, DC National Mall

3 out of 5
Southwest
Save 100% on your flight
Price was $889, price is now $633 per person
$633
per person
Oct 20 - Oct 22
found 1 day 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
Crystal City
Price was $674, price is now $486 per person
$486
per person
Oct 20 - Oct 22
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
Downtown Washington D.C.
Save 100% on your flight
Price was $1,307, price is now $961 per person
$961
per person
Oct 20 - Oct 22
found 1 day ago
Roundtrip 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)
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)

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 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 $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 23 hours 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 19 hours 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 19 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)
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 23 hours 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)
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 11 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)
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)
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 11 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)
Glover Park Hotel Georgetown

Glover Park Hotel Georgetown

4 out of 5
Price was $734, price is now $574 per person
$574
per person
Sep 24 - Sep 28
found 11 hours ago
Roundtrip flight included
Tampa (TPA) to Baltimore (BWI)
Morrison Clark Historic Inn

Morrison Clark Historic Inn

4 out of 5
Save 100% on your flight
Price was $2,210, price is now $1,745 per person
$1,745
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Baltimore (BWI)

5-night Dorchester County vacations

Price found within the past 48 hours. Click for updated prices.
Graves Mountain Farm & Lodges

Graves Mountain Farm & Lodges

3.5 out of 5
Price was $917, price is now $904 per person
$904
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop 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 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 16 hours ago
$750
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Sep 10 from New York to Salisbury, returning Sun, Sep 13, priced at $750 found 16 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.
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 26 - Aug 27
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
$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
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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.