Dorchester County Vacation Packages
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Your Dorchester County Vacation
Reserve a vacation package to Dorchester County and go wherever your adventurous soul takes you. This exciting destination has much to offer, including its watersports, culture, golfing, and so much more. A trip to Dorchester County promises plenty to see and do. Not sure where to start? Cambridge is one of the most popular places to stay here. When it's time to stop daydreaming and start doing, Expedia will help turn your Dorchester County vacation into a reality.
Top vacation destinations in Dorchester County
Cambridge
Top Dorchester County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Westin DC Downtown
Downtown Washington D.C.
CA $656
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (1,006 reviews)
The staff and accommodations were excellent. Late check-out and luggage storage for our late flight was easy.
Our room was clean and all the amenities were great.
Reviewed on Aug 15, 2026
Furnished Apartments
Ashton Heights
CA $890
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Baltimore (BWI)
9/10 Wonderful! (4 reviews)
Location is excellent. Walking distance to pretty much everything you need. Space was very comfortable, clean, and the bed was excellent for sleeping. Lots of light and windows.
Host was helpful and able to accommodate my schedule needs too.
Reviewed on Apr 1, 2025
Dorchester County Hotel Deals
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
CA $271
CA $373 total
Sep 2 - Sep 3
includes taxes & fees
Days Inn & Suites by Wyndham Cambridge
2917 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
CA $106
CA $118 total
Aug 16 - Aug 17
includes taxes & fees
Comfort Inn & Suites Cambridge
2936 Ocean Gtwy Cambridge MD
Fully refundable
CA $161
CA $178 total
Sep 7 - Sep 8
includes taxes & fees
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.
Frequently asked questions
How much does a Dorchester County vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Dorchester County from just CA $656. And the more you bundle, the more cash you save. The vacation of your dreams has never been so affordable.
How do I get a cheap travel package to Dorchester County?
Just think of all the wonderful things you could do in Dorchester County with a pile of extra cash in your wallet. Watch your savings stack up when you bundle your airfare and hotel bookings into a Dorchester County vacation package. You have loads of choice when it comes to booking with Expedia too. In fact, you can select from more than 550 airlines and 1,000,000 hotel options worldwide. Whether you're heading off with the entire family or flying solo, organizing a getaway to Dorchester County is better with a package.
What are the top hotels in Dorchester County?
When it comes to properties in Cambridge, Hyatt Regency Chesapeake Bay and Comfort Inn & Suites Cambridge are two excellent options. If you're also spending time in East New Market, Holiday Inn Express Cambridge, an IHG Hotel and Days Inn & Suites by Wyndham Cambridge will make you feel at home.
How far in advance should I book my Dorchester County vacation?
Browse Expedia to compare international flights as soon as you've got your travel dates. In most cases, you can purchase a seat up to a year in advance. If you can't see your preferred air carrier, or you're booking late, don't worry. The lowest prices to Dorchester County sometimes occur a few weeks before the date of departure.
What does an Expedia Dorchester County travel package include?
Travel packages include hotels, flights and rental cars, but you can mix and match them to create your ideal Dorchester County vacation. You can also add on tours and activities once you've made your booking. You're in the driver's seat! When you bundle your bookings with Expedia, you'll score discounts you won't find anywhere else.
What should I know before booking a Dorchester County travel package?
When you book your hotels, flights and car rentals together, you'll pick up incredible discounts. Whether you're organizing a rural escape in a cottage or would rather stay in a cozy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a Dorchester County Expedia vacation package?
Yes, and with more than 550 airlines to select from throughout the world, you have plenty of choice. Browse the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Dorchester County vacation package?
Don't worry if you're rethinking your Dorchester County vacation package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We totally get that life can sometimes throw a spanner in the works, so head to our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
Stay near popular Dorchester County attractions
Blackwater National Wildlife Refuge
8.8/10 (172 reviews)
Discover a sanctuary for birds, reptiles, amphibians and mammals on Maryland's Eastern Shore in this beautiful area rich in wetlands, forest and meadows.
Long Wharf Park
9.2/10 (64 reviews)
Find this lovely park along the shoreline and enjoy many exciting tourist attractions in Cambridge. It’s a pleasant spot for a fun day outdoors.
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.
Choptank River Lighthouse
9.2/10 (46 reviews)
Enjoy scenic views of the Choptank River from the beautiful replica of a historic lighthouse and learn about Cambridge’s rich maritime heritage.
Dorchester County Visitors Center
9.6/10 (34 reviews)
Pick up useful information with interesting details about Chesapeake Bay and relax at this center with beautiful outdoor areas and activities.
Gerry Boyle Park at Great Marsh
9.0/10 (60 reviews)
Explore the great outdoors at Gerry Boyle Park at Great Marsh, a lovely green space in Cambridge. Wander around the natural setting or enjoy the area's seafood restaurants.
Harriet Tubman Museum and Educational Center
9.6/10 (87 reviews)
You can spend an afternoon browsing the exhibits at Harriet Tubman Museum and Educational Center during your travels in Cambridge. While you're in the area, stroll along the riverfront.
Lower Hooper Island
10.0/10 (1 review)
Commune with nature and explore the great outdoors at Lower Hooper Island during your travels in Fishing Creek.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
