Southern Oregon Romantic Vacations 2026

Top Romantic vacation packages in Southern Oregon

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

McCall House Boutique Inn

Historic Downtown District

$619

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.2/10 Wonderful! (608 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southern Oregon

View all trips

3 Night Romantic vacations in Southern Oregon

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

McCall House Boutique Inn

Historic Downtown District

$619

per person

Dec 18 - Dec 21

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.2/10 Wonderful! (608 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Southern Oregon

View all trips

4 Night Romantic vacations in Southern Oregon

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

Wine Country Inn

$417

per person

Nov 6 - Nov 10

found 20 hours ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.4/10 Exceptional! (1,004 reviews)

The rooms are very clean and spacious.

Reviewed on Sep 28, 2026

Weasku Inn

$585

per person

Nov 6 - Nov 10

found 20 hours ago

Roundtrip flight included

Los Angeles (LAX) to Medford (MFR)

9.8/10 Exceptional! (1,003 reviews)

Our local get away for a wonderful, relaxing weekend. Very quiet and serene. The room is always clean and well stocked. Bonus for us is the complimentary afternoon hors d’oeuvres, in the little dining area. Also, the chocolate chip cookies in the evening are wonderful! They also have a smores kit to enjoy if you are lucky enough to get a spot around the beautiful fire pit in the evening. Light breakfast selection in the morning is also very good!

Reviewed on Sep 28, 2026

Lithia Springs Resort

$727

per person

Nov 12 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Houston (HOU) to Medford (MFR)

9.4/10 Exceptional! (1,000 reviews)

Room was very clean. Staff was not especially welcoming. Dogs in a room near ours were loud. Bed was mushy (perhaps old & time to be replaced?)

Reviewed on Sep 25, 2026

Don't see what you're looking for?

See all available trips from Columbus to Southern Oregon

View all trips

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 $417. 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, ...

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! (241 reviews)

"Enjoyed walking on the trails, we had some wildlife visitors. I like to check the birds in the area in my Merlin app and found 6 new birds in the area. The house was beautiful and everything the same as advertised."

Reviewed on Aug 31, 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 1,443 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.