A town nestled in a valley with a prominent building in the foreground and hills in the background.

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Our top choices for Southern Oregon romantic hotels

1. The Ashland Cottage, walk to town

The Ashland Cottage, walk to town
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (241 reviews)
"Beautiful location, comfortable, and nice touches! Loved our stay here."
United States
Julie S.
The price is ¥26,197
¥44,778 total
includes taxes & fees
Nov 1 - Nov 2
The Ashland Cottage, walk to town

2. Cozy Cottage Close to Crater Lake

Cozy Cottage Close to Crater Lake
Fort Klamath
9.2 out of 10, Wonderful, (107 reviews)
"Mountain view, nice stay"
United States
Vickie
The price is ¥21,177
¥35,214 total
includes taxes & fees
Oct 28 - Oct 29
Cozy Cottage Close to Crater Lake

3. Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Central Point
9.8 out of 10, Exceptional, (129 reviews)
"Wonderful stay and will definitely do so again!!!"
United States
Kelly B.
The price is ¥15,373
¥27,883 total
includes taxes & fees
Nov 1 - Nov 2
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

4. Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland
Historic Downtown District
9.8 out of 10, Exceptional, (137 reviews)
"Room was in fantastic shape, clean, well decorated, close to everything. As an Air B&B owner, I recommend, if staying Ashland stay here. Great host."
United States
James C.
The price is ¥19,766
¥40,755 total
includes taxes & fees
Nov 2 - Nov 3
Oberon -Second Spring Property 1-3 Bedroom Luxury Rentals In Downtown Ashland

5. 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.
Jacksonville Historic District
9.8 out of 10, Exceptional, (85 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"
United States
Richard
The price is ¥12,989
¥45,256 total
includes taxes & fees
Oct 29 - Oct 30
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.

6. Historic Bradshaw House!

Historic Bradshaw House!
Jacksonville
10.0 out of 10, Exceptional, (71 reviews)
"We’ve stayed in Vrbo’s around the world and this is by far our favorite."
United States
Robert B.
The price is ¥18,040
¥42,683 total
includes taxes & fees
Oct 28 - Oct 29
Historic Bradshaw House!

7. Cottage with gated driveway near downtown & river

Cottage with gated driveway near downtown & river
Grants Pass
10.0 out of 10, Exceptional, (32 reviews)
"It’s a great place to stay"
United States
Greg S.
The price is ¥17,726
¥37,746 total
includes taxes & fees
Nov 11 - Nov 12
Cottage with gated driveway near downtown & river

8. Home with gated driveway near River & Downtown

Home with gated driveway near River & Downtown
Grants Pass
9.8 out of 10, Exceptional, (43 reviews)
"Everything was lovely, clean and really liked the fact that it's near everything. Will definitely stay again. "
United States
Ester
The price is ¥20,550
¥45,403 total
includes taxes & fees
Oct 28 - Oct 29
Home with gated driveway near River & Downtown

9. Cozy Historic Cabin Near Hiking

Cozy Historic Cabin Near Hiking
Wolf Creek
9.2 out of 10, Wonderful, (17 reviews)
"Great place, super hosts, wonderful hikes in the area, and quiet and secluded."
United States
Roy R.
The price is ¥24,707
¥35,586 total
includes taxes & fees
Oct 28 - Oct 29
Cozy Historic Cabin Near Hiking

10. 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
10.0 out of 10, Exceptional, (244 reviews)
"We appreciated that the lodging was remote enough to be quiet, and offered hiking opportunities within steps of the home. The kitchen was particularly well equipped, making it easy for meal preparation."
United States
Anonymous traveler
The price is ¥35,923
¥64,486 total
includes taxes & fees
Nov 1 - Nov 2
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
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.

Find out more about Southern Oregon

Southern Oregon attractions for couples

Southern Oregon is a paradise for adventurous families eager to explore a blend of nature and culture. Start your journey in Ashland, home to the renowned Oregon Shakespeare Festival, where you can catch world-class performances in a charming town filled with art galleries and cozy cafes. Just a short drive away, the breathtaking landscapes of Crater Lake National Park await, offering stunning views of the deepest lake in the U.S., perfect for hiking, photography, or simply soaking in the awe-inspiring beauty. Families can enjoy a day at the Rogue River, where white-water rafting and scenic float trips promise thrilling adventures suitable for all ages. Don’t miss the opportunity to visit the Oregon Caves National Monument, where you can take guided tours through fascinating marble caves and learn about their unique geological formations. Lastly, the picturesque town of Jacksonville, with its historic buildings and local wineries, is ideal for leisurely strolls and tastings. When it comes to accommodations, consider staying in the heart of Ashland, where you’ll find boutique hotels that offer personalized service and convenient access to the town’s attractions. After a day full of exploration, unwind in these quality establishments that cater to families, ensuring a comfortable and memorable experience.

Top Southern Oregon Hotel Reviews

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