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

A marina with several boats docked, a building with a sign, and trees in the background.
FlightsFlightsHotelsHotels

Cambridge

Cambridge

Top Dorchester County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Omni Shoreham Hotel

Omni Shoreham Hotel

4 out of 5
Northwest
Price was CA $976, price is now CA $732 per person
CA $732
per person
Sep 21 - Sep 23
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Baltimore (BWI)
9/10 Wonderful! (2,363 reviews)
The food was great, The room was greatly sized. But the closet in the room had a moldy smell. Which over came the room.

Reviewed on Jun 30, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,508, price is now CA $1,029 per person
CA $1,029
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
8.2/10 Very good! (1,001 reviews)
No bar and you have to pay extre for parking $$ per night

Reviewed on Jun 28, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was CA $2,497, price is now CA $1,741 per person
CA $1,741
per person
Sep 9 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Baltimore (BWI)
9/10 Wonderful! (1,203 reviews)
Every staff member we interacted with seemed completely disinterested in the guests. The woman at the front desk put us in one of the absolute worst rooms and didn’t explain how to reach the room which was on the second floor behind some doors that looked like big brown swinging kitchen doors. My husband and I were celebrating our 30th anniversary and wanted to go someplace special - we were so disappointed in the Sofitel DC experience. We will never go there again!

Reviewed on Jun 28, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $4,818, price is now CA $3,669 per person
CA $3,669
per person
Aug 9 - Aug 16
found 1 hour ago
Roundtrip flight included
Calgary (YYC) to Salisbury (SBY)
9.4/10 Exceptional! (779 reviews)
This hotel was beyond my expectations, the King room had a beautiful balcony, which you could see some of the beach from, the bed and pillows were great! I loved that it actually had a refrigerator and dishwasher in it and microwave and Keurig. As well as a sectional sofa which had a pull out bed, the bathroom was spacious and beautiful! Family friendly. Was pleasantly surprised with all of the details and the staff. We were only there for 1 night - quick trip but definitely will return.

Reviewed on Jun 30, 2026

The River Inn

The River Inn

4 out of 5
Northwest
Price was CA $1,178, price is now CA $931 per person
CA $931
per person
Aug 24 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Baltimore (BWI)
9.4/10 Exceptional! (1,999 reviews)
Staff went above and beyond to accommodate us early, provide directions and treat us so nicely.

Reviewed on Jun 30, 2026

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
The price is CA $425 per night from Jul 6 to Jul 7
CA $425
CA $550 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Dealing with billing issue. Other than that, great place to stay."

Reviewed on Jun 26, 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
The price is CA $115 per night from Jul 14 to Jul 15
CA $115
CA $127 total
Jul 14 - Jul 15
includes taxes & fees
6.6/10 (1,003 reviews)
"This location has really gone downhill! We stayed there in October 2025, and it was good, especially for the price, but now, I will not stay there again! First of all at check-in, we were told that the Apple Pay machine was not working and would not be working and that was how I had planned on paying ..."

Reviewed on Jun 27, 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
The price is CA $107 per night from Jul 1 to Jul 2
CA $107
CA $118 total
Jul 1 - Jul 2
includes taxes & fees
5.4/10 (577 reviews)
"Parking was a problem based on handicap."

Reviewed on Jun 30, 2026

Cambridge Inn
See all 1,141 properties in Dorchester County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $732. 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

A wooden boardwalk extending into a grassy field.

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