Southern Oregon Romantic Vacations
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Top Romantic vacation packages in Southern Oregon
Price found within the past 48 hours. Click for updated prices.
- Rogue Regency Inn Medford Airport
Sep 10 - Sep 14Rogue Regency Inn Medford Airport + Flight
Medford4 nights3.0 star property8.8/10 - Excellent (3,191 reviews)"This hotel was pleasant. You can tell it was very nice back in the day and it was very clean, but it hasn’t been updated in quite some time. It was charming and the staff were very friendly and welcoming. We didn’t get the opportunity to use the pool or gym, but the included buffet breakfast spread was nice. We went back to Chadwick’s, the on site restaurant, for a late dinner and our food was tasty (and we were grateful they were open until 10 pm on a Sunday). Checking in and out was a breeze..."Reviewed August 4, 2026Roundtrip • Denver (DEN) - Medford (MFR)DEN - MFR • Nonstop MFR - DEN • Nonstop$555$505found 14 hours agoper traveler - Lithia Springs Resort
Sep 10 - Sep 14Lithia Springs Resort + Flight
Ashland4 nights3.0 star property9.4/10 - Exceptional (1,002 reviews)"At our approach to the property, I was fairly underwhelmed. But, once you get past the gates, they do a fairly good job of reducing the fact that you are right off I5. The property was lovely and relaxing, and the rooms were fairly well maintained. Grows for the property would be: remove the jetted tubs in the rooms and replace with soaking tubs since the mineral water has corroded the metal jets to the point that our intake was no longer connected and appeared to be mended with a screw that..."Reviewed August 5, 2026Roundtrip • Denver (DEN) - Medford (MFR)DEN - MFR • Nonstop MFR - DEN • Nonstop$911$813found 14 hours agoper traveler - McCall House Boutique Inn
Oct 10 - Oct 12McCall House Boutique Inn + Flight
Historic Downtown District2 nights4.0 star property9.2/10 - Wonderful (603 reviews)Roundtrip • Dallas (DFW) - Medford (MFR)DFW - MFR • 1 stop MFR - DFW • 1 stop$920$838found 22 hours agoper traveler - Hummingbird Estate Wine & Suites
Sep 18 - Sep 21Hummingbird Estate Wine & Suites + Flight
Central Point3 nights4.5 star property9.6/10 - Exceptional (176 reviews)"Great experienc"Reviewed August 3, 2026Roundtrip • Dallas (DFW) - Medford (MFR)DFW - MFR • 1 stop MFR - DFW • 2 stops$957$876found 22 hours agoper traveler - Green Springs Inn
Sep 18 - Sep 21Green Springs Inn + Flight
Ashland3 nights2.0 star property9.2/10 - Wonderful (142 reviews)"Very basic."Reviewed August 2, 2026Roundtrip • Dallas (DFW) - Medford (MFR)DFW - MFR • 1 stop MFR - DFW • 2 stops$841$787found 22 hours agoper traveler
Discover the most popular places to visit in Southern Oregon
Photo by Patrick Glassford
Open Photo by Patrick Glassford
Oregon Shakespeare Festival
9.2/10 (620 reviews)
At OSF, America's oldest repertory theater presents Shakespearean classics and bold new works across three venues. Reserve seats for evening performances and arrive early for the free outdoor Green Show entertainment.
Top Romantic Southern Oregon Hotels
Cozy Cottage Close to Crater Lake
Cozy Cottage Close to Crater Lake11.3 mi from Southern Oregon
9.2 out of 10, Wonderful, (93 reviews)
9.2/10
Wonderful
(93 reviews)
"It’s a little gem. It’s a small but exceedingly well equipped cottage in a great location."
$203 nightly
The price is $222
$222 total
Aug 11 - Aug 12
Total with taxes and fees
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub48.2 mi from Southern Oregon
9.8 out of 10, Exceptional, (124 reviews)
9.8/10
Exceptional
(124 reviews)
"We loved our stay. It is a very cozy, clean, quiet, place to stay. The hosts have truly thought of everything."
$143 nightly
The price is $161
$161 total
Aug 9 - Aug 10
Total with taxes and fees
Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.
Charming Jacksonville cottage with a front porch, full kitchen, off-street parking, and walkable access to Britt Festival, downtown shops, restaurants, and wine tasting. Features two bedrooms, two bathrooms, and peaceful historic charm.51.8 mi from Southern Oregon
9.8 out of 10, Exceptional, (84 reviews)
9.8/10
Exceptional
(84 reviews)
"What an adorable cottage. It’s right in town but on a quiet street. It had every amenity that we needed. I would very highly recommend and would stay here again"
$345 nightly
The price is $369
$369 total
Aug 6 - Aug 7
Total with taxes and fees
Cottage with gated driveway near downtown & river
Cottage with gated driveway near downtown & river67.6 mi from Southern Oregon
10.0 out of 10, Exceptional, (25 reviews)
10/10
Exceptional
(25 reviews)
"It’s a great place to stay"
$200 nightly
The price is $227
$227 total
Aug 10 - Aug 11
Total with taxes and fees
Home with gated driveway near River & Downtown
Home with gated driveway near River & Downtown67.6 mi from Southern Oregon
9.8 out of 10, Exceptional, (43 reviews)
9.8/10
Exceptional
(43 reviews)
"This home is wonderfully decorated and very comfortable. It had all the amenities that anyone would need and we really enjoyed the back patio and bbq. It is close to shopping and many restaurants. "
$240 nightly
The price is $272
$272 total
Aug 19 - Aug 20
Total with taxes and fees
Cozy Historic Cabin Near Hiking
Cozy Historic Cabin Near Hiking68.9 mi from Southern Oregon
9.2 out of 10, Wonderful, (16 reviews)
9.2/10
Wonderful
(16 reviews)
"It would be perfect for someone trying to escape the business of city life or someone who needs total peace and quiet! The room and home are old but nicely decorated the grounds are beautiful and the people are friendly. I didn’t realize just how remote it was until I arrived and that made me feel somewhat uneasy the girls also were bored but if I needed some time to myself and rest it was perfect!"
$221 nightly
The price is $224
$224 total
Aug 6 - Aug 7
Total with taxes and fees
The Ashland Cottage, walk to town
The Ashland Cottage, walk to town43.6 mi from Southern Oregon
10.0 out of 10, Exceptional, (232 reviews)
10/10
Exceptional
(232 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
$258 nightly
The price is $288
$288 total
Aug 17 - Aug 18
Total with taxes and fees
Historic Bradshaw House!
Historic Bradshaw House!51.9 mi from Southern Oregon
10.0 out of 10, Exceptional, (70 reviews)
10/10
Exceptional
(70 reviews)
"Creatively decorated and cozy. Bed a bit lumpy but overall a lovely little cottage perfectly located next to Main Street."
$269 nightly
The price is $289
$289 total
Aug 6 - Aug 7
Total with taxes and fees
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.
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.
How to find a romantic Southern Oregon vacation
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 $505. 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?