Southern Oregon Romantic Vacations 2026

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4 Night Romantic vacations in Southern Oregon

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

Wine Country Inn

$272

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Las Vegas (LAS) to Medford (MFR)

9.4/10 Exceptional! (1,008 reviews)

Weasku Inn

$443

per person

Nov 5 - Nov 9

found 1 day ago

Roundtrip flight included

Las Vegas (LAS) to Medford (MFR)

9.6/10 Exceptional! (1,004 reviews)

Classic lodge, I'm ready to go back.

Reviewed on Sep 12, 2026

Winchester Inn

Historic Downtown District

$505

per person

Nov 5 - Nov 9

found 19 hours ago

Roundtrip flight included

Las Vegas (LAS) to Medford (MFR)

9.6/10 Exceptional! (285 reviews)

Our stay at the Winchester Inn was very pleasant and enjoyable. The complimentary made to order breakfast was delicious, and the room was very comfortable and quiet. The location was very convenient and walkable to downtown's many excellent restaurants and the Shakespeare Festival. Would definitely stay there again.

Reviewed on Sep 5, 2026

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

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Southern Oregon romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Southern Oregon?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Southern Oregon?

Put a price on love with stunning deals for duos starting at just $272. Prices and availability are subject to change. Additional terms may apply.

Can I book Southern Oregon spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Southern Oregon?

To book a loved-up break in Southern Oregon, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

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

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

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

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?

Top Romantic Southern Oregon Hotels

Callahan's Mountain Lodge

7100 Old Highway 99 South Ashland OR

2 hours drive from Crater Lake National Park

If you're in the mood for love, consider staying at this romantic lodge, featuring al fresco dining and a garden. You'll also love the jetted tubs, lobby fireplace, ...

8.8/10 Excellent! (1,147 reviews)

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

Travelers say...

"Very friendly staff. Older but cozy and spacious rooms. A wonderfully quiet, relaxed atmosphere."

Reviewed on Sep 10, 2026

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 vacation home in Prospect. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mill Creek Falls and Barr Creek Falls are located ...

10/10 Exceptional! (240 reviews)

"Beautiful ranch setting. Hiking trails. Porches for sitting. Ranch manager very helpful. Good pizza at Crater Lake Pizza. Good food at Prospect Cafe.Lovely house.Great for touring NP"

Reviewed on Aug 28, 2026

Ashland Springs Hotel

212 E Main St Ashland OR

2 hours drive from Crater Lake National Park

A spa, a garden, and a hot tub await couples looking for a romantic getaway at this historic hotel. The property also offers a lobby fireplace, premium mattresses, ...

See all 1,470 properties in Southern 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.