Southern Oregon Romantic Holidays

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

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    Better together
    Save up to £335 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

How to find a romantic Southern Oregon holiday

How can I find the best Southern Oregon vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Southern Oregon. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Southern Oregon romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Southern Oregon that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Southern Oregon romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Southern Oregon?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Southern Oregon?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Southern Oregon that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Southern Oregon with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Southern Oregon romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Southern Oregon Hotels

Callahan's Mountain Lodge
Callahan's Mountain Lodge
3 out of 5
7100 Old Highway 99 South, Ashland, OR
  • 2 hours drive from Crater Lake National Park
Stay at this 3-star family-friendly lodge in Ashland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the restaurant in ...
8.6/10 Excellent! (1,149 reviews)

Couples like: al fresco dining, hot tub, romance packages available

Travellers say...
"What a great find. If I travel this route again, I will be sure to stop."

Reviewed on 2 Jul 2025

Callahan's Mountain Lodge
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
Prospect, OR
  • 32 min drive from Crater Lake National Park
Stay at this holiday home in Prospect. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Mill Creek Falls and Barr Creek Falls are located ...
10/10 Exceptional! (162 reviews)

Couples like: adults-only property, fireplace

Crater Lake Trip
"This place was amazing! Everything you could possibly need. Beautiful home and property. Highly recommend."

Reviewed on 18 Jun 2025

Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
Ashland Springs Hotel
Ashland Springs Hotel
3 out of 5
212 E Main St, Ashland, OR
  • 2 hours drive from Crater Lake National Park
Stay at this 3-star spa hotel in Ashland. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the breakfast and the helpful staff in their ...
9.2/10 Wonderful! (1,001 reviews)

Couples like: full-service spa, couples spa treatments, bar, hot tub

Travellers say...
"It’s an over 100 year hotel with old world charm. Stay knowing rooms and bathrooms will be smaller than modern hotels. But the charm and ease of getting around downtown made it well worth it."

Reviewed on 4 Jul 2025

Ashland Springs Hotel
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 holidays you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.