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
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Cambridge

Cambridge

Top Dorchester County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Price was CA $1,269, price is now CA $886 per person
CA $886
per person
May 1 - May 5
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (DCA)
8.4/10 Very Good! (1,002 reviews)
Staff was awsome. Clean room. Breakfast was ok.

Reviewed on Feb 15, 2026

Kimpton Banneker Hotel by IHG

Kimpton Banneker Hotel by IHG

4.5 out of 5
Downtown Washington D.C.
Price was CA $2,789, price is now CA $1,924 per person
CA $1,924
per person
May 15 - May 18
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (637 reviews)
Friendly stuff, comfortable beds, robes and excellent restaurant.

Reviewed on Feb 14, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was CA $2,267, price is now CA $1,580 per person
CA $1,580
per person
May 15 - May 18
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.6/10 Excellent! (1,008 reviews)
Large room great restaurant next door, attentive staff.

Reviewed on Feb 20, 2026

Rosewood Washington, D.C.

Rosewood Washington, D.C.

5 out of 5
Northwest
Price was CA $3,989, price is now CA $2,802 per person
CA $2,802
per person
Apr 16 - Apr 19
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
9.2/10 Wonderful! (194 reviews)
My stay at the Rosewood Hotel was absolutely wonderful from start to finish. The level of service, attention to detail, and overall atmosphere made it a truly memorable experience. From the moment I arrived, the staff was warm, welcoming, and genuinely attentive. Check‑in was smooth and effortless, and I immediately felt like a valued guest. The room was beautifully designed—spacious, spotless, and thoughtfully arranged with luxurious touches throughout. The bed was incredibly comfortable, and the overall ambiance made it easy to relax. The hotel’s amenities were equally impressive. Whether enjoying the dining options, unwinding in the lounge areas, or simply taking in the elegant décor, everything felt refined and well-curated. Every interaction with the staff felt sincere, and the service consistently exceeded my expectations. Overall, my stay at the Rosewood was exceptional. I would highly recommend this hotel to anyone looking for comfort, luxury, and top‑tier hospitality. I’m already looking forward to returning!

Reviewed on Feb 19, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,553, price is now CA $1,119 per person
CA $1,119
per person
May 15 - May 18
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.2/10 Very Good! (1,002 reviews)
Staff is great. We love this hotel because it has plenty of self parking, so not having to wait for the valet to get your car every time saves a ton of time. The hotel is within the Gallaudet campus which is beautiful and feels very safe. The only issue we had were with the room itself. The furniture and fixtures are a bit dated/worn, though the beds are very comfortable. The sink drain was frozen in the bathroom, the toilet flusher was stuck. We managed to get around these things since we were only there one night and it would not deter us from coming again.

Reviewed on Dec 11, 2025

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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 $254 per night from Mar 2 to Mar 3
CA $254
CA $328 total
Mar 2 - Mar 3
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
The staff was very nice and helpful. The room was clean but cold. Even though we had the thermostat set to 74, it was still cold. All the amenities were great. It would have been nice if the room beds had been made and if fresh towels had been left in the room. Housekeeping didn't show up until 5:30 ...

Reviewed on Feb 22, 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 $97 per night from Feb 25 to Feb 26
CA $97
CA $108 total
Feb 25 - Feb 26
includes taxes & fees
6.6/10 (1,002 reviews)
Very comfortable and quiet

Reviewed on Feb 14, 2026

Days Inn & Suites by Wyndham Cambridge
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge MD
10/10 Exceptional! (265 reviews)
The property is lovely, and so are the hosts. We were all very happy with our stay. Cambridge is an interesting place, and the views from our unit were spectacular. So much to do just being on the property. We all enjoyed our long weekend.

Reviewed on Dec 3, 2025

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Family and Pet-Friendly, Waterfront with Pier
See all 1,082 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.
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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 $886. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.