Book Exclusive Dorchester County Vacation Packages

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Dorchester County flight + hotel packages

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
Downtown Washington D.C.
Price was CA $1,370, price is now CA $1,023 per person
CA $1,023
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions White House and Washington Monument are located nearby.
Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

5 out of 5
Northwest
Price was CA $2,028, price is now CA $1,442 per person
CA $1,442
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Lincoln Memorial are located nearby.
Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was CA $1,652, price is now CA $1,182 per person
CA $1,182
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Capital One Arena and Smithsonian Institution are located nearby.
Placemakr Dupont Circle

Placemakr Dupont Circle

4 out of 5
Northwest
Price was CA $2,036, price is now CA $1,462 per person
CA $1,462
per person
Oct 18 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
Stay at this aparthotel in Washington. Enjoy free WiFi, a 24-hour fitness center, and 2 meeting rooms. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions White House and Smithsonian's National Zoo are located nearby.
Willard InterContinental Washington by IHG

Willard InterContinental Washington by IHG

5 out of 5
Downtown Washington D.C.
Price was CA $2,846, price is now CA $2,063 per person
CA $2,063
per person
Oct 26 - Oct 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions White House and National Mall are located nearby.

Top Dorchester County hotels deals

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
The price is CA $281 per night
CA $281
CA $385 total
Sep 2 - Sep 3
includes taxes & fees
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dorchester County Historical Society and Bay Country Shop are located nearby.
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
The price is CA $94 per night
CA $94
CA $104 total
Aug 27 - Aug 28
includes taxes & fees
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions Bay Country Shop and Dorchester County Historical Society are located nearby.
Pool
Breakfast included
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
Free cancellation
The price is CA $165 per night
CA $165
CA $183 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this business-friendly hotel in Cambridge. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Bay Country Shop and Dorchester County Historical Society are located nearby.
Pool
Breakfast included
Private 2 Acre Waterfront Family Retreat with Pool & Pier

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cambridge MD
Get rates
Book a stay at this family-friendly vacation home in Cambridge. Enjoy free WiFi, private pools, and a garden. Popular attractions Christ Rock Park and Spocott Windmill are located nearby.
Pool
Kitchen
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
The price is CA $112 per night
CA $112
CA $123 total
Aug 31 - Sep 1
includes taxes & fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Saint Michaels Village and Classic Motor Museum are located nearby.
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Free cancellation
Reserve now, pay when you stay
The price is CA $123 per night
CA $123
CA $183 total
Sep 3 - Sep 4
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chesapeake Beach Railway Museum and Rod n Reel Charter Fishing are located nearby.
Pool
Spa
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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.

Stay near popular Dorchester County attractions

A marina with numerous sailboats docked at wooden piers.

Long Wharf Park

9.2/10 (64 reviews)
Long Wharf Park is just one of the places to see in Cambridge, so why not enjoy the other things to explore during your travels? Wander around the natural setting or enjoy the area's seafood restaurants.
See properties

Photos of local treasures

Browse Dorchester County vacation photos for more inspiration

A lighthouse on a pier with a red roof and white walls, surrounded by calm water.
A lighthouse on a pier with seagulls.
A small building with a sign reading "Emily's Produce".
A visitor center with a sign for the Harriet Tubman Underground Railroad Visitor Center, surrounded by a grassy area and a stone wall.
A wooden pier extending into a body of water during sunset.

Frequently asked questions

How much are vacation packages to Dorchester County?
Travelocity has package deals to Dorchester County, as well as flights and hotels, starting from as low as CA $1,023. With all that extra cash, you could book some popular tours or perhaps even add on a couple of extra days to your adventure.
Where can I get the best vacation package deals for Dorchester County?
You can lock in sensational Dorchester County package deals with Travelocity. Choose from 400 airlines and 1,000,000 worldwide properties and turn those travel dreams into a reality.
Why should I purchase my Dorchester County vacation package via Travelocity?
We've got destinations and experiences to suit every kind of traveler, top-notch service and support available 24/7. On top of that, we'll match any better price you happen to find with our Price Match Guarantee.
Can I save on my Dorchester County car rental if I combine it with my hotel or flight?
Bundling your bookings into a Dorchester County vacation package will certainly save you money. You can combine a car and flight; a flight, car and hotel; or a hotel and car. You won't find a better way to explore the greater Dorchester County region than from behind the wheel of your own rental car. You can also add activities and experiences to your Travelocity package.
Which airport is best for Dorchester County?
Ronald Reagan Washington National Airport (DCA) is a popular option for those flying to Dorchester County. Baltimore Washington Intl. Thurgood Marshall Airport (BWI) and Salisbury - Ocean City Wicomico Regional Airport (SBY) also welcome many of the region's flights.
What is there to do in Dorchester County?
A diverse and lively destination, Dorchester County boasts some excellent sights and attractions. Layton's Chance Vineyard and Winery and Elliott Island are among the most renowned here.