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.
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 CA $1,480, price is now CA $1,027 per person
CA $1,027
per person
Dec 26 - Jan 1
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Arlington. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions National Mall and White House are located nearby.
Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was CA $2,087, price is now CA $1,355 per person
CA $1,355
per person
Dec 26 - Jan 1
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, breakfast (surcharge), and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.
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 CA $2,558, price is now CA $1,682 per person
CA $1,682
per person
Nov 24 - Nov 28
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
Book a stay at this luxury B&B in Ridge. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Saint Jerome Beach and First District Community Park are located nearby.
Club Quarters Hotel White House, Washington DC

Club Quarters Hotel White House, Washington DC

3 out of 5
Downtown Washington D.C.
Price was CA $1,906, price is now CA $1,378 per person
CA $1,378
per person
Dec 26 - Jan 1
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
Book a stay at this business-friendly hotel in Washington. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White House and Capital One Arena are located nearby.
Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
Price was CA $1,633, price is now CA $1,213 per person
CA $1,213
per person
Dec 26 - Jan 1
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) 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 bar in our reviews. Popular attractions White House and Capital One Arena 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 $255 per night
CA $255
CA $330 total
Nov 9 - Nov 10
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 $108 per night
CA $108
CA $120 total
Nov 8 - Nov 9
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
Cambridge Inn

Cambridge Inn

2 out of 5
2831 Ocean Gateway Cambridge MD
Free cancellation
Reserve now, pay when you stay
The price is CA $107 per night
CA $107
CA $118 total
Oct 11 - Oct 12
includes taxes & fees
Stay at this hotel in Cambridge. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Bay Country Shop and Dorchester County Historical Society are located nearby.
Pet-friendly
Parking 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 $158 per night
CA $158
CA $175 total
Nov 8 - Nov 9
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
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek MD
Get rates
Book a stay at this family-friendly cottage in Fishing Creek. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions P. L. Jones Marina and Gunners Island are located nearby.
Kitchen
Pet-friendly
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 $122 per night
CA $122
CA $134 total
Nov 1 - Nov 2
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.
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.

Stay near popular Dorchester County attractions

A modern building with a sign reading "Harriet Tubman Underground Railroad Visitor Center".

Harriet Tubman Underground Railroad National Historical Park

9.6/10 (95 reviews)
You can spend time studying the exhibits at Harriet Tubman Underground Railroad National Historical Park in Madison. While you're in the area, stroll along the riverfront.
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 $1,027. 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.