Highland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Highland

Price found within the past 48 hours. Click for updated prices.
The Nines, a Luxury Collection Hotel, Portland
Rockaway Shores
Stunning Ocean Views, Steps to Beach Tranquil Retreat Cove Keep by Avantstay
SaltLine Hotel
Heathman Hotel

Where to stay in Highland

Find the best Highland areas and neighborhoods for the activities you enjoy most. Learn more about Highland

Highland Hotel Deals

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 10 to Aug 11
CA $150
CA $175 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (3,512 reviews)
"Very happy with price and everything. Id happily stay here again."

Reviewed on Jul 15, 2026

The Paramount Hotel
The Duniway Portland A Hilton Hotel

The Duniway Portland A Hilton Hotel

4.5 out of 5
545 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $223 per night from Aug 2 to Aug 3
CA $223
CA $259 total
Aug 2 - Aug 3
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Clean space, easy check in especially for a last minute booking through Expedia. Staff was super helpful"

Reviewed on Jul 15, 2026

The Duniway Portland A Hilton Hotel
Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street Portland OR
Fully refundable
The price is CA $156 per night from Jul 19 to Jul 20
CA $156
CA $183 total
Jul 19 - Jul 20
includes taxes & fees
Courtyard by Marriott Portland City Center
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.

Things to do

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