Dorchester County Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Mary Pat Collins

Top destinations in Dorchester County

Aerial panorama of Chesapeake City Maryland historic fishing town on the Chesapeake Delaware canal with private boats docked in the marina and the Chesapeake City Bridge over the back creek
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Fishing Creek

Fishing Creek

Top hotels in Dorchester County

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 6.136.754 ₫ per night from 5 May to 6 May
6.136.754 ₫
8.221.538 ₫ total
5 May - 6 May
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Had a great time will be back soon

Reviewed on 6 Apr 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 2.037.244 ₫ per night from 29 Apr to 30 Apr
2.037.244 ₫
2.261.340 ₫ total
29 Apr - 30 Apr
includes taxes & fees
6.6/10 (1,005 reviews)
Was very easy access from the highway. The staff was very pleasant.

Reviewed on 13 Apr 2026

Days Inn & Suites by Wyndham Cambridge
Holiday Inn Express Cambridge by IHG

Holiday Inn Express Cambridge by IHG

2.5 out of 5
2715 Ocean Gtwy Cambridge MD
Fully refundable
The price is 3.344.799 ₫ per night from 3 May to 4 May
3.344.799 ₫
3.712.727 ₫ total
3 May - 4 May
includes taxes & fees
8.8/10 Excellent! (774 reviews)
Room was impeccable, staff professional and courteous, room somewhat noisy due to being right off Ocean Gateway. Overall it was a good stay.

Reviewed on 17 Apr 2026

Holiday Inn Express Cambridge by IHG
See all 1,101 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.

Frequently asked questions

How much does a Dorchester County holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Dorchester County from just . And the more you bundle, the more cash you save. The holiday 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 holiday 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 1null000null000 hotel options worldwide. Whether you're heading off with the entire family or flying solo, organising 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 holiday?
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 holiday. 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 organising a rural escape in a cottage or would rather stay in a cosy apartment in the city, Expedia can make it happen for less.
Can I choose my airline with a Dorchester County Expedia holiday 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 holiday package?
Don't worry if you're rethinking your Dorchester County holiday 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.