Western Oregon Luxury Vacations

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Flight and Luxury hotel deals in Western Oregon

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

Hotel deLuxe

Downtown Portland
CA $681
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.6/10 Excellent! (1,082 reviews)
RiverPlace Hotel

RiverPlace Hotel

Downtown Portland
CA $902
per person
Oct 29 - Nov 2
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9.2/10 Wonderful! (1,003 reviews)
I supposed to get 20% off when I dine at their restaurant. But they didn’t honor that.

Reviewed on Aug 13, 2026

Sentinel Hotel

Sentinel Hotel

Downtown Portland
CA $794
per person
Oct 29 - Nov 2
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.8/10 Excellent! (1,001 reviews)
Fantastic hotel Wright in the middle of the city perfect for walking about restaurants shows. Highly recommend.

Reviewed on Aug 14, 2026

The Herondale Hotel

The Herondale Hotel

CA $766
per person
Oct 23 - Oct 26
found 2 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9/10 Wonderful! (1,002 reviews)
We had a room on the second floor facing the Columbia river. Was beautiful, peaceful, and very quiet. We definitely would stay there again.

Reviewed on Aug 15, 2026

Salishan Coastal Lodge

Salishan Coastal Lodge

CA $1,116
per person
Sep 25 - Sep 28
found 24 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PDX)
8.8/10 Excellent! (1,006 reviews)
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5* Luxury holidays in Western Oregon

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

Sentinel Hotel

Downtown Portland
CA $794
per person
Oct 29 - Nov 2
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.8/10 Excellent! (1,001 reviews)
Fantastic hotel Wright in the middle of the city perfect for walking about restaurants shows. Highly recommend.

Reviewed on Aug 14, 2026

The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

Downtown Portland
CA $1,235
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Portland (PDX)
9.2/10 Wonderful! (1,007 reviews)
Very central to downtown and very well kept hotel. Friendly staff.

Reviewed on Aug 14, 2026

Don't see what you're looking for?
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3 Night Luxury holidays in Western Oregon

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

Hotel deLuxe

Downtown Portland
CA $681
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.6/10 Excellent! (1,082 reviews)
Heathman Hotel

Heathman Hotel

Downtown Portland
CA $947
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to Portland (PDX)
9.2/10 Wonderful! (1,033 reviews)
Sentinel Hotel

Sentinel Hotel

Downtown Portland
CA $785
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.8/10 Excellent! (1,001 reviews)
Fantastic hotel Wright in the middle of the city perfect for walking about restaurants shows. Highly recommend.

Reviewed on Aug 14, 2026

Don't see what you're looking for?
See all available trips from Columbus to Western Oregon
View all trips

4 Night Luxury holidays in Western Oregon

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

Hotel deLuxe

Downtown Portland
CA $742
per person
Sep 17 - Sep 21
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.6/10 Excellent! (1,082 reviews)
The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

Downtown Portland
CA $814
per person
Oct 29 - Nov 2
found 20 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9.2/10 Wonderful! (1,007 reviews)
Very central to downtown and very well kept hotel. Friendly staff.

Reviewed on Aug 14, 2026

Mark Spencer Hotel

Mark Spencer Hotel

Downtown Portland
CA $824
per person
Sep 17 - Sep 21
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9.2/10 Wonderful! (2,365 reviews)
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Plan the perfect luxury Western Oregon vacation with Expedia

What are some benefits when booking luxury Western Oregon vacations?

When you book a luxury Western Oregon vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Western Oregon?

If you're looking for something luxurious in Western Oregon, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $681, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 18. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Western Oregon. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Western Oregon?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Western Oregon.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Western Oregon. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Western Oregon?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Western Oregon or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Western Oregon. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Western Oregon

The Benson Portland, Curio Collection by Hilton

The Benson Portland, Curio Collection by Hilton

309 SW Broadway Portland OR
  • 7 hours drive from Crater Lake National Park
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
The Benson Portland, Curio Collection by Hilton
Heathman Hotel

Heathman Hotel

1001 SW Broadway Portland OR
  • 7 hours drive from Crater Lake National Park
Book a stay at this luxury hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
Heathman Hotel
The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

525 SW Morrison Street Portland OR
  • 7 hours drive from Crater Lake National Park
Book a stay at this luxury hotel in Portland. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the property condition ...
9.2/10 Wonderful! (1,002 reviews)
"Very central to downtown and very well kept hotel. Friendly staff."

Reviewed on Aug 14, 2026

The Nines, a Luxury Collection Hotel, Portland
See all 12,208 properties in Western Oregon
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.

More vacations you might like

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