Oregon Luxury Vacations 2026

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Top Luxury vacation packages in Oregon

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

Heathman Hotel

Downtown Portland

$352

per person

Nov 7 - Nov 9

found 14 hours ago

Roundtrip flight included

Los Angeles (LAX) to Portland (PDX)

9.2/10 Wonderful! (1,070 reviews)

This is a great old hotel downtown with a library and guest lounge space. Rooms are well appointed and staff are efficient and helpful

Reviewed on Sep 7, 2026

Juniper Preserve

Pronghorn

$861

per person

Nov 8 - Nov 14

found 7 hours ago

Roundtrip non-stop flight included

Indianapolis (IND) to Redmond (RDM)

9/10 Wonderful! (691 reviews)

Beautiful place to stay. Clean, friendly staff. The breakfast at the restaurant was excellent!

Reviewed on Sep 5, 2026

RiverPlace Hotel

Downtown Portland

$400

per person

Nov 7 - Nov 9

found 14 hours ago

Roundtrip flight included

Los Angeles (LAX) to Portland (PDX)

9.2/10 Wonderful! (1,001 reviews)

Hotel deLuxe

Downtown Portland

$405

per person

Nov 7 - Nov 9

found 14 hours ago

Roundtrip flight included

Los Angeles (LAX) to Portland (PDX)

8.6/10 Excellent! (1,109 reviews)

Very friendly staff, and close to transit

Reviewed on Sep 7, 2026

Embassy Suites by Hilton Portland Downtown

Downtown Portland

$825

per person

Nov 8 - Nov 13

found 6 hours ago

Roundtrip flight included

Los Angeles (LAX) to Portland (PDX)

8.8/10 Excellent! (1,589 reviews)

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See all available trips from Columbus to Oregon

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5* Luxury vacations in Oregon

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

Sentinel Hotel

Downtown Portland

$442

per person

Nov 7 - Nov 9

found 14 hours ago

Roundtrip flight included

Los Angeles (LAX) to Portland (PDX)

8.8/10 Excellent! (1,005 reviews)

What a truly wonderful experience. Staff were friendly, helpful, and incredibly kind. The hotel was amazing and the room was perfection wrapped in a bow. Thank you so much for an amazing experience!

Reviewed on Sep 6, 2026

The Nines, a Luxury Collection Hotel, Portland

Downtown Portland

$897

per person

Oct 7 - Oct 10

found 19 hours ago

Roundtrip non-stop flight included

New York (NYC) to Portland (PDX)

9.2/10 Wonderful! (1,000 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Oregon

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3 Night Luxury vacations in Oregon

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

Heathman Hotel

Downtown Portland

$382

per person

Nov 10 - Nov 13

found 3 hours ago

Roundtrip flight included

Denver (DEN) to Portland (PDX)

9.2/10 Wonderful! (1,070 reviews)

This is a great old hotel downtown with a library and guest lounge space. Rooms are well appointed and staff are efficient and helpful

Reviewed on Sep 7, 2026

RiverPlace Hotel

Downtown Portland

$493

per person

Nov 10 - Nov 13

found 3 hours ago

Roundtrip flight included

Denver (DEN) to Portland (PDX)

9.2/10 Wonderful! (1,001 reviews)

Juniper Preserve

Pronghorn

$549

per person

Nov 21 - Nov 24

found 18 hours ago

Roundtrip non-stop flight included

Austin (AUS) to Redmond (RDM)

9/10 Wonderful! (691 reviews)

Beautiful place to stay. Clean, friendly staff. The breakfast at the restaurant was excellent!

Reviewed on Sep 5, 2026

Don't see what you're looking for?

See all available trips from Columbus to Oregon

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4 Night Luxury vacations in Oregon

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

Heathman Hotel

Downtown Portland

$530

per person

Oct 7 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to Portland (PDX)

9.2/10 Wonderful! (1,070 reviews)

This is a great old hotel downtown with a library and guest lounge space. Rooms are well appointed and staff are efficient and helpful

Reviewed on Sep 7, 2026

The Nines, a Luxury Collection Hotel, Portland

Downtown Portland

Save 100% on your flight

$864

per person

Oct 7 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to Portland (PDX)

9.2/10 Wonderful! (1,000 reviews)

Mark Spencer Hotel

Downtown Portland

$565

per person

Oct 7 - Oct 11

found 1 day ago

Roundtrip non-stop flight included

Nashville (BNA) to Portland (PDX)

9.2/10 Wonderful! (2,416 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Oregon

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What can I expect from a luxury Oregon vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Oregon vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Oregon?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Oregon luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $352. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Oregon?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Oregon with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Oregon?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Oregon with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Oregon with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Oregon Hotels

The Benson Portland, Curio Collection by Hilton

309 SW Broadway Portland OR

7 hours drive from Crater Lake National Park

$137 nightly

$159 total

Sep 19 - Sep 20

Total with taxes and fees

Discover luxurious lodging at The Benson Portland, Curio Collection by Hilton, where you can enjoy amenities like premium mattresses, Egyptian cotton sheets, ...

Heathman Hotel

1001 SW Broadway Portland OR

7 hours drive from Crater Lake National Park

$154 nightly

$179 total

Sep 20 - Sep 21

Total with taxes and fees

Treat yourself to some luxurious accommodations at Heathman Hotel, where you can enjoy amenities like designer toiletries, HDTVs, and more. Sought-after amenities ...

9.2/10 Wonderful! (1,075 reviews)

"This is a great old hotel downtown with a library and guest lounge space. Rooms are well appointed and staff are efficient and helpful"

Reviewed on Sep 7, 2026

The Nines, a Luxury Collection Hotel, Portland

525 SW Morrison Street Portland OR

7 hours drive from Crater Lake National Park

$238 nightly

$278 total

Sep 25 - Sep 26

Total with taxes and fees

The Nines, a Luxury Collection Hotel, Portland is one of the Portland luxury 5-star boutique properties where you can pamper yourself with pillowtop beds, rainfall ...

See all 19,009 properties in 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.