Southern Oregon Romantic Holidays
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Top Romantic Southern Oregon Hotels
Callahan's Mountain Lodge
7100 Old Highway 99 South, Ashland, OR
Stay at this 3-star family-friendly lodge in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in ...
8.6/10 Excellent! (1,150 reviews)
"What a great find. If I travel this route again, I will be sure to stop."
Reviewed on 2 Jul. 2025
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
Prospect
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! (162 reviews)
Crater Lake Trip
"This place was amazing! Everything you could possibly need. Beautiful home and property. Highly recommend."
Reviewed on 18 Jun. 2025
Ashland Springs Hotel
212 E Main St, Ashland, OR
Stay at this 3-star spa hotel in Ashland. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the breakfast and the helpful staff in our ...
9.2/10 Wonderful! (1,002 reviews)
"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
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.