Willamette Valley Luxury Vacations

Book a Luxury Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 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 Luxury vacation packages in Willamette Valley

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Portland Downtown

The Royal Sonesta Portland Downtown

Downtown Portland
¥236,445
per person
Nov 12 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
9.2/10 Wonderful! (1,365 reviews)
I love this hotel. Very kind staff. I forgot toothpaste, has some brought up. I love the wallpaper and the quirky touches

Reviewed on Oct 2, 2026

Heathman Hotel

Heathman Hotel

Downtown Portland
¥238,067
per person
Nov 12 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
9.2/10 Wonderful! (1,090 reviews)
Great place.

Reviewed on Oct 1, 2026

Hotel deLuxe

Hotel deLuxe

Downtown Portland
¥239,460
per person
Nov 12 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
8.6/10 Excellent! (1,128 reviews)
Staff were very helpful and pleasant. Our room was clean. Bed was comfy. It is a very intersting hotel...fancy. The restaurant in the hotel waan't my favourite food. Paid parking...across the street in a parking garage. Tea ..coffee and water in the lobby which was nice.

Reviewed on Oct 2, 2026

The Hotel Zags Portland

The Hotel Zags Portland

Downtown Portland
¥236,809
per person
Nov 12 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
8.6/10 Excellent! (1,236 reviews)
There was an added per night amenities fee charged at the hotel that covers the mediocre free breakfast, their arcade games, the nightly s'mores and their equipment room. We did not use any of these amenities so it was quite a bit of cost added to the stay. There is also a daily parking fee and the parking is very limited They ran out of spaces so we had to park on the street our last night there.

Reviewed on Oct 1, 2026

Dossier Hotel

Dossier Hotel

Downtown Portland
¥238,301
per person
Nov 12 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
9.2/10 Wonderful! (1,552 reviews)
Don't see what you're looking for?
See all available trips from Osaka to Willamette Valley
View all trips

3 Night Luxury vacations in Willamette Valley

Price found within the past 48 hours. Click for updated prices.
The Hotel Zags Portland

The Hotel Zags Portland

Downtown Portland
¥236,809
per person
Nov 12 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
8.6/10 Excellent! (1,236 reviews)
There was an added per night amenities fee charged at the hotel that covers the mediocre free breakfast, their arcade games, the nightly s'mores and their equipment room. We did not use any of these amenities so it was quite a bit of cost added to the stay. There is also a daily parking fee and the parking is very limited They ran out of spaces so we had to park on the street our last night there.

Reviewed on Oct 1, 2026

Heathman Hotel

Heathman Hotel

Downtown Portland
¥238,067
per person
Nov 12 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
9.2/10 Wonderful! (1,090 reviews)
Great place.

Reviewed on Oct 1, 2026

Hotel deLuxe

Hotel deLuxe

Downtown Portland
¥239,460
per person
Nov 12 - Nov 15
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
8.6/10 Excellent! (1,128 reviews)
Staff were very helpful and pleasant. Our room was clean. Bed was comfy. It is a very intersting hotel...fancy. The restaurant in the hotel waan't my favourite food. Paid parking...across the street in a parking garage. Tea ..coffee and water in the lobby which was nice.

Reviewed on Oct 2, 2026

Don't see what you're looking for?
See all available trips from Osaka to Willamette Valley
View all trips

4 Night Luxury vacations in Willamette Valley

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

Heathman Hotel

Downtown Portland
¥227,732
per person
Nov 19 - Nov 23
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
9.2/10 Wonderful! (1,090 reviews)
Great place.

Reviewed on Oct 1, 2026

Hotel deLuxe

Hotel deLuxe

Downtown Portland
¥231,953
per person
Nov 19 - Nov 23
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
8.6/10 Excellent! (1,128 reviews)
Staff were very helpful and pleasant. Our room was clean. Bed was comfy. It is a very intersting hotel...fancy. The restaurant in the hotel waan't my favourite food. Paid parking...across the street in a parking garage. Tea ..coffee and water in the lobby which was nice.

Reviewed on Oct 2, 2026

Mark Spencer Hotel

Mark Spencer Hotel

Downtown Portland
¥234,895
per person
Nov 19 - Nov 23
found 6 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Portland (PDX)
9.2/10 Wonderful! (2,469 reviews)
Don't see what you're looking for?
See all available trips from Osaka to Willamette Valley
View all trips

Top Luxury Willamette Valley Hotels

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
Discover luxurious lodging at The Benson Portland, Curio Collection by Hilton, where you can enjoy amenities like premium mattresses, Egyptian cotton sheets, ...
9.2/10 Wonderful! (1,433 reviews)
"Good location. Helpful and courteous staff."

Reviewed on Sep 30, 2026

The Benson Portland, Curio Collection by Hilton
Heathman Hotel

Heathman Hotel

1001 SW Broadway Portland OR
  • 7 hours drive from Crater Lake National Park
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! (1,084 reviews)
"Great place."

Reviewed on Oct 1, 2026

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
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 ...
The Nines, a Luxury Collection Hotel, Portland
See all 5,471 properties in Willamette Valley
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

Meet the growers of these dynamic vintages

Private Wine Excursion Willamette Valley, Oregon - Wine Tour

¥45,495
per adult
Private Wine Excursion Willamette Valley, Oregon - Wine Tour
Private Willamette Valley Wine Tour

Private Willamette Valley Wine Tour

¥206,836
per traveler
Private Willamette Valley Wine Tour
See all activities in Willamette Valley
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.