Southern Oregon Luxury Vacations

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

4 Night Luxury vacations in Southern Oregon

Price found within the past 48 hours. Click for updated prices.
Rogue Regency Inn and Suites
Ashland Springs Hotel
Ashland Hills Hotel & Suites
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All you need to know about luxury vacations in Southern Oregon

What can I expect from a luxury Southern Oregon vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Southern 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 Southern 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 Southern 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 $443. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Southern 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 Southern 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 Southern 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 Southern 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 Southern 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 Southern Oregon Hotels

Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3 out of 5
98 Central Ave, Ashland, OR
  • 2 hours drive from Crater Lake National Park
Plaza Inn & Suites at Ashland Creek delivers luxe lodging where you'll enjoy premium bedding and more. Notable amenities include a 24-hour fitness center, a ...
8.6/10 Excellent! (1,011 reviews)
We were traveling with a pet and it was very easy with convenient parking and walkability to town. The room was very clean and the bed was comfortable. There were many hot breakfast item choices. Overall we had a pleasant stay and would happily stay again!

Reviewed on Oct 17, 2025

Plaza Inn & Suites at Ashland Creek
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St, Ashland, OR
  • 2 hours drive from Crater Lake National Park
Be treated to a luxury stay at Ashland Springs Hotel, where you can enjoy amenities like Frette Italian sheets, pillowtop beds, and more. The spa, restaurant, ...
9.2/10 Wonderful! (1,007 reviews)
Lovely music & coffee on the mezzanine in a.m. Beautiful decor. Comfortable bedding. Tea & cookies on the mezzanine in the afternoon. An orientation to amenities on arrival would have been helpful.

Reviewed on Oct 4, 2025

Ashland Springs Hotel
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St, Ashland, OR
  • 2 hours drive from Crater Lake National Park
Treat yourself to a luxury stay at Ashland Hills Hotel & Suites, where you can enjoy amenities like premium channels, flat-screen TVs, and more. Deluxe amenities ...
8.8/10 Excellent! (1,482 reviews)
Nice simple hotel. Comfortable and convenient location. Nothing fancy, but perfectly adequate.

Reviewed on Oct 24, 2025

Ashland Hills Hotel & Suites
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.

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