Highland Vacation Packages

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Top Holiday Package Deals in Highland

Price found within the past 48 hours. Click for updated prices.
Park Lane Suites and Inn

Park Lane Suites and Inn

Southwest Portland
CA $646
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.6/10 Excellent! (1,931 reviews)
The location was perfect for attending the Timber’s game at Providence Park. The room was very clean and it was nice to have a small refrigerator in the room. The air conditioner and bed springs were a bit loud, but we would definitely stay here again.

Reviewed on Sep 12, 2026

Hotel deLuxe

Hotel deLuxe

Downtown Portland
CA $705
per person
Dec 1 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.6/10 Excellent! (1,109 reviews)
The Tillamook Inn

The Tillamook Inn

CA $1,007
per person
Oct 14 - Oct 19
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
8/10 Very good! (1,255 reviews)
No good, glorified motel 6… very displeased with the price for what the place is…

Reviewed on Sep 13, 2026

Darlingwood

Darlingwood

CA $1,240
per person
Oct 14 - Oct 19
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
9.6/10 Exceptional! (4 reviews)
The setting is tranquil, with beautiful views, and the home itself is lovely. Our host was welcoming and gracious. The B&B is about two miles down gravel roads with fairly deep washboards, so guests should be prepared for a rough drive. We love staying at true bed and breakfasts, and for us, part of the charm is the experience of a thoughtfully prepared, homemade breakfast. Unfortunately, the breakfast we received was a bit disappointing—a scone, two strawberries, and five blueberries left us wanting more. In fairness, the fault is partly ours for not having more realistic expectations about what was included. The property and setting are beautiful, and the host was very welcoming, but the breakfast experience did not live up to what we typically expect from a bed and breakfast.

Reviewed on Aug 10, 2026

Schooner Landing

Schooner Landing

Agate Beach
CA $1,089
per person
Oct 14 - Oct 19
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
8.4/10 Very good! (78 reviews)
Great, quiet, relaxing. Young person at check in/out was great and very professional. Nest time we wil request a ground floor unit so no stairs. Thanks for the stay!

Reviewed on Aug 30, 2026

Where to stay in Highland

Find the best Highland areas and neighborhoods for the activities you enjoy most. Learn more about Highland
An aerial view of a city with a prominent building in the center, surrounded by smaller buildings and a parking lot.

Central Area

7 out of top 10 points of interest in this area

If you're spending some time in Central Area, Elsinore Theater and Oregon State Capitol are top sights worth seeing.

A large building with a statue on top, surrounded by cherry blossom trees.

Southeast Salem

While visiting Southeast Salem, you might make a stop by sights like Honeywood Winery and Wunderland.

A pedestrian bridge over a river, surrounded by greenery and a large globe sculpture.

West Salem

When in West Salem, you can plan a visit to Salem Riverfront Carousel and Elsinore Theater, some noteworthy sights in the nearby area.

A waterfall surrounded by dense forest and a wooden fence.

Northgate

1 out of top 10 points of interest in this area

While visiting Northgate, you might make a stop by sights like L. B. Day Amphitheater and Oregon State Fairgrounds Pavilion.

A waterfall under a rock overhang with a forested valley below.

North East Salem

Though North East Salem might not have many top sights, you can venture to the surrounding area to see attractions like Oregon State Fairgrounds Pavilion and L. B. Day Amphitheater.

Highland Hotel Deals

Oregon Garden Resort

Oregon Garden Resort

895 W Main St Silverton OR
Fully refundableReserve now, pay when you stay
CA $143
CA $158 total
Oct 14 - Oct 15
includes taxes & fees
9.4/10 Exceptional! (1,067 reviews)
"We were able to check in early and take in the Oregon Garden! It was a nice addition to our hotel stay. We had hiked in Silver Falls State Park earlier in the day and drove to Silverton and stayed at this resort on our way to the coast. It was perfect for us. We ate at the restaurant on Friday night ..."

Reviewed on Sep 13, 2026

Oregon Garden Resort
Best Western Plus Mill Creek Inn

Best Western Plus Mill Creek Inn

3125 Ryan Drive SE Salem OR
Fully refundableReserve now, pay when you stay
CA $164
CA $185 total
Oct 4 - Oct 5
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
"Great budget place to stay"

Reviewed on Sep 12, 2026

Best Western Plus Mill Creek Inn
La Quinta Inn & Suites by Wyndham Salem OR

La Quinta Inn & Suites by Wyndham Salem OR

890 Hawthorne Avenue SE Salem OR
Fully refundableReserve now, pay when you stay
CA $146
CA $164 total
Sep 20 - Sep 21
includes taxes & fees
8.4/10 Very good! (1,056 reviews)
"Staffs are very helpful and friendly, room is clean, and very comfortable bed. Good breakfast."

Reviewed on Sep 13, 2026

La Quinta Inn & Suites by Wyndham Salem OR
See all 392 properties in Highland
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

get into the photo at our favorite waterfalls!

Silver Falls Waterfall Hiking Tour from Portland

CA $137
per adult
100% of travellers recommend
Silver Falls Waterfall Hiking Tour from Portland
Seven Falls Hiking Tour at Silver Falls State Park

Seven Falls Hiking Tour at Silver Falls State Park

CA $248
per adult
100% of travellers recommend
Seven Falls Hiking Tour at Silver Falls State Park
Amazing Scavenger Hunt: Salem Oregon's Beautiful Capital

Amazing Scavenger Hunt: Salem Oregon's Beautiful Capital

CA $17
per adult
Amazing Scavenger Hunt: Salem Oregon's Beautiful Capital
See all activities in Salem
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.