Southern Oregon Romantic Holidays
Book a Hotel + Flight or Car together to unlock savings
Better together
Save up to RM 324 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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)
Couples like: al fresco dining, hot tub, romance packages available
Travellers say...
"What a great find. If I travel this route again, I will be sure to stop."
Reviewed on 2 Jul 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! (1,003 reviews)
Couples like: full-service spa, couples spa treatments, bar, hot tub
Lovely hotel
"Our family had a great stay at the Ashland Springs. There were eight of us staying in three different rooms, and had many quiet places to gather on the grounds there. The grounds and rooms were clean and lovely, and we enjoyed exploring the many places there to relax. Their staff was efficient and ..."
Reviewed on 30 Jun 2025
McCall House Boutique Inn
153 Oak St, Ashland, OR
Stay at this 4-star B&B in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9.8/10 Exceptional! (264 reviews)
Couples like: champagne service, romance packages available
Travellers say...
"Absolutely wonderful!"
Reviewed on 22 Jun 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.