Durham Region Vacations & Trips from $677

Book a Hotel + Flight or Car together to unlock savings

Your Durham Region Vacation

Leave the travel planning to us with a Durham Region vacation package. With everything organized before you go, the only thing left for you to do is sit back, chill out and experience this destination's beauty and culture. Begin your trip to Durham Region by spending a few days exploring Pickering, one of the best cities here. Quit dreaming and get packing, because your Durham Region vacation is only clicks away with Expedia.

Top destinations in Durham Region

I've heard it is closed but it was open (and so awesome) when I was there last
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Clarington

Clarington

The Latest Durham Region Vacation Packages

Price found within the past 48 hours. Click for updated prices.
New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

4 out of 5
Price was $983, price is now $677 per person
$677
per person
Dec 6 - Dec 14
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
8.4/10 Very Good! (21 reviews)
The house its-self was beautiful! Location was convenient. However, I've never stayed in a place that house keeping doesn't check the dishwasher and drier before the next tenant. Showed up at 7pm to a dishwasher full of "clean dishes" that still had food all over them. And their trash was still there. I emailed them to let them know about dishes and trash so I wouldn't get charged. They seemed confused about my complaint. Sure enough when we left we got charged for some of the last tenants garbage.

Reviewed on Aug 25, 2025

Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5
Clifton Hill
Save 100% on your flight
Price was $1,355, price is now $898 per person
$898
per person
Dec 6 - Dec 14
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (1,989 reviews)
The room was spacious. Loved the shower! The staff was wonderful and helped me with a unique situation. I highly recommend

Reviewed on Sep 15, 2025

Woodbourne Inn

Woodbourne Inn

4 out of 5
St. Davids
Save 100% on your flight
Price was $1,252, price is now $834 per person
$834
per person
Oct 25 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.8/10 Exceptional! (495 reviews)
We, mother and daughter from Japan enjoyed every minute of our stay at Woodbourne Inn. Warm welcome, beautiful place, great breakfast, and so on. A winery with an excellent restaurant is within walking distance.

Reviewed on Aug 24, 2025

Downtown Toronto near CN Tower

Downtown Toronto near CN Tower

3 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,481, price is now $1,014 per person
$1,014
per person
Nov 28 - Dec 3
found 13 hours ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
8.2/10 Very Good! (45 reviews)
Very good location, very good host, very good stay.

Reviewed on Sep 12, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,393, price is now $957 per person
$957
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (587 reviews)
Clean room, nice restaurants and polite staff.

Reviewed on Sep 8, 2025

Durham Region Hotel Deals

Pickering Casino Resort Hotel

Pickering Casino Resort Hotel

4 out of 5
888 Durham Live Ave, Pickering, ON
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $103 total per night from Oct 13 to Oct 14
$103 total
Oct 13 - Oct 14
Total with taxes and fees
8.8/10 Excellent! (3,290 reviews)
"Excellent"

Reviewed on Sep 10, 2025

Pickering Casino Resort Hotel
Travelodge by Wyndham Oshawa Whitby

Travelodge by Wyndham Oshawa Whitby

2 out of 5
940 Champlain Avenue, Oshawa, ON
Fully refundableReserve now, pay when you stay
$66 nightly
The price is $78 total per night from Oct 6 to Oct 7
$78 total
Oct 6 - Oct 7
Total with taxes and fees
6.6/10 (1,000 reviews)
"Carpet in the hallway was tired"

Reviewed on Sep 8, 2025

Travelodge by Wyndham Oshawa Whitby
Super 8 by Wyndham Ajax/Toronto On

Super 8 by Wyndham Ajax/Toronto On

2 out of 5
210 Westney Rd S, Ajax, ON
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $90 total per night from Sep 28 to Sep 29
$90 total
Sep 28 - Sep 29
Total with taxes and fees
6.8/10 (1,177 reviews)
"Close to everything, good place to stay for Blue Jays baseball."

Reviewed on Sep 12, 2025

Super 8 by Wyndham Ajax/Toronto On
See all 509 properties in Durham Region
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
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Durham Region vacation package cost?
We make it simple to travel somewhere new, with Durham Region packages starting from as little as $677. You'll have the flexibility to combine your favorite hotels, airlines and car rental. For the ultimate getaway, why not add a couple of tours and experiences to your travel itinerary?
How do I get a cheap travel package to Durham Region?
Combine your bookings with Expedia to save big on your next exciting adventure. With more than 550 air carriers and 1,000,000 properties worldwide, your Durham Region vacation package can be customized exactly to suit your budget. With all that extra money, why not add one or two exciting activities and tours? It's an easy way to unlock even more bargains. That dream vacation to Durham Region is much closer than you thought!
How far in advance should I book my Durham Region vacation?
Be rewarded with the biggest variety at the lowest prices by booking your Durham Region vacation nice and early. Air carriers generally sell flight tickets around a year prior to departure, so secure your spot ASAP. That being said, Expedia is dedicated to providing you with the best deals around, so it's always a good time to book your dream vacation!
What does an Expedia Durham Region travel package include?
You can choose from a combination of flights, rental cars and hotels. Once you've made your booking, you can add some tours and experiences. Want to pick your fare class? That's also easy to do. The choice is yours when it comes to crafting your dream Durham Region getaway.
What should I know before booking a Durham Region travel package?
When you book your hotels, flights and car rentals together, you'll enjoy great discounts. Whether you're planning an outdoor getaway in a chalet or want to stay in a convenient hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a Durham Region Expedia vacation package?
Yes, you're in control. Expedia has access to more than 550 airlines worldwide, so you can customize your Durham Region vacation according to your travel preferences.
Does Expedia offer Book Now, Pay Later Durham Region vacation packages?
Expedia has teamed up with online lender Affirm to help minimize any financial concerns related to your trip. This may be useful if your need to travel has arisen unexpectedly. Book Now, Pay Later and split the price of your activities and hotel package booking over several installments.
If I'm not able to travel, can I cancel my Durham Region vacation package?
It's hard to predict what tomorrow might bring, so it's comforting to know that you can change or cancel your Durham Region vacation package. If your booking was made in the last 24 hours, you may be eligible for a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to find out more.
Explore a world of travel with Expedia

Explore a world of travel with Expedia

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