Dorchester County Vacations & Trips from $341

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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 destinations in Dorchester County

The Latest Dorchester County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University
Historic Inns of Annapolis
The Westin Annapolis
Sheraton Baltimore North Hotel
Comfort Inn & Suites Lexington Park near Pax River

Find the Best Dorchester County Vacation Packages

Dorchester County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Salisbury - Ocean City Wicomico Regional Airport (SBY)
Top Sights
Great Marsh Park, Long Wharf Park and Dorchester County Visitors Center

Dorchester County Hotel Deals

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$322 nightly
The price is $366 total per night from Aug 3 to Aug 4
$366 total
Aug 3 - Aug 4
Total with taxes and fees
8.8/10 Excellent! (1,011 reviews)
"Hello, my stay was wonderful. The service was excellent, the room was cleaned every day, and the staff's attentiveness was outstanding. Everything was great—100% recommended. Thank you."

Reviewed on Jul 12, 2026

Hyatt Regency Chesapeake Bay
Days Inn & Suites by Wyndham Cambridge

Days Inn & Suites by Wyndham Cambridge

2.5 out of 5
2917 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $90 total per night from Jul 16 to Jul 17
$90 total
Jul 16 - Jul 17
Total with taxes and fees
6.6/10 (1,007 reviews)
"It Needs A Lot of TLC to bring it back to its Glory Days. Outside the building looks Run Down, Dirty, Dirty Windows, Blinds. Lobby was ok, Front Desk Staff Nice, Didn’t Smell Bad, Our Room, Ok, Need More Staff to Clean The Hotel, Mirror in Room, Broken, Microwave Very Dirty, Not Clean, The Carpet ..."

Reviewed on Jul 12, 2026

Days Inn & Suites by Wyndham Cambridge
Cambridge Inn

Cambridge Inn

2 out of 5
2831 Ocean Gateway Cambridge MD
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $83 total per night from Jul 14 to Jul 15
$83 total
Jul 14 - Jul 15
Total with taxes and fees
5.4/10 (581 reviews)
"Very clean and quite"

Reviewed on Jul 6, 2026

Cambridge Inn
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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.