Portland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Portland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Greenwood by IHG
Price was CA $1,574, price is now CA $1,226 per person
CA $1,226
per person
Jun 17 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9/10 Wonderful! (1,012 reviews)
Great place off the expressway. Staff were great!
Reviewed on Apr 10, 2026
Ironworks Hotel Indy
Price was CA $1,937, price is now CA $1,546 per person
CA $1,546
per person
Jun 17 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9.8/10 Exceptional! (1,855 reviews)
Rize is a great restaurant! The only additional requests I would ask is that a small personal fridge be an option, or an option to clean the mini bar since it’s not weighted. As well as an option to include a microwave in the room. Though not all stays are extended beyond a day or two, families still love to stay here and may be staying for a few days. This would support those extended stays, just as options to be added into the room, or in the mini bars case, the fridge to be cleared.
Reviewed on Apr 10, 2026
Omni Severin Hotel
Downtown Indianapolis
Price was CA $1,741, price is now CA $1,420 per person
CA $1,420
per person
Jun 17 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9.4/10 Exceptional! (899 reviews)
I really enjoyed my stay at the Omni. The hotel is aesthetically pleasing (great for pictures) and very clean. The staff was wonderful and friendly. The food I had at 8 Notch, which is a breakfast/ lunch style restaurant downstairs, was good. I will definitely stay here in the future.
Reviewed on Apr 1, 2026
Bottleworks Hotel
Downtown Indianapolis
Price was CA $2,185, price is now CA $1,826 per person
CA $1,826
per person
Jun 17 - Jun 21
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Indianapolis (IND)
9.8/10 Exceptional! (1,849 reviews)
This is a great hotel with fabulous staff!
Reviewed on Apr 10, 2026
Portland Hotel Deals
Holiday Inn Express & Suites Portland by IHG
100 Holiday Dr Portland IN
Fully refundable
The price is CA $152 per night from Apr 26 to Apr 27
CA $152
CA $170 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (364 reviews)
Outstanding - highest rating possible - in all regards of customer service!
Reviewed on Apr 7, 2026
Motel 6 Portland, IN
1147 US-27 Portland IN
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Apr 12 to Apr 13
CA $104
CA $116 total
Apr 12 - Apr 13
includes taxes & fees
6.8/10 (82 reviews)
When we arrived we were told no rooms were available as they had no water. Told us they called us, but they didn’t leave a message letting us know the room reservations was canceled
Reviewed on Mar 9, 2026
Hoosier Inn
1620 N Meridian St Portland IN
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Apr 26 to Apr 27
CA $103
CA $115 total
Apr 26 - Apr 27
includes taxes & fees
8.8/10 Excellent! (138 reviews)
Excellent staff
Reviewed on Feb 13, 2026
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.
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.
