Dorchester County Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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Top destinations in Dorchester County

FlightsFlightsHotelsHotels

Cambridge

Cambridge

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 S$417 per night from 14 Jun to 15 Jun
S$417
14 Jun - 15 Jun
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The service was exceptional."

Reviewed on 1 Jun, 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 S$114 per night from 21 Jun to 22 Jun
S$114
21 Jun - 22 Jun
includes taxes & fees
6.6/10 (1,002 reviews)
"I booked this place last minute just to spend a quick night after a change of plans in our trip due to weather. The place is simply disgusting. Don’t stay here. I never thought a Wyndham branded property could be this filthy. Shame on them for not verifying the basic cleanliness of a hotel they allow ..."

Reviewed on 29 May, 2026

Days Inn & Suites by Wyndham Cambridge
Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge

2.5 out of 5
2936 Ocean Gtwy Cambridge MD
Fully refundable
The price is S$180 per night from 17 Jun to 18 Jun
S$180
17 Jun - 18 Jun
includes taxes & fees
8.2/10 Very Good! (845 reviews)
"Staff was excellent, rooms very clean good working refrigerator. Bed slept well. It was a wonderful 3 day stay I would definitely go back"

Reviewed on 1 Jun, 2026

Comfort Inn & Suites Cambridge
See all 1,136 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 1,000,000 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.