Luxury Retreats in Ashland, Oregon with Outdoor Pools

7100 Old Hwy 99 S, Ashland, OR 97520, USA

“Just off Old Hwy 99, Callahan’s Restaurant makes an easy date-night stop for couples driving into Ashland, with cozy lodge-style dining, a relaxed pace, and hearty Northwest fare that suits lingering over a shared entrée and a glass of local wine.”

100 Eagle Mill Rd, Ashland, OR 97520, USA

“At Wild Garden Medicinals, couples wander quiet garden paths and shaded nooks off Eagle Mill Road, pausing to breathe in the herb-scented air and share a low-key picnic amid native plants.”

2455 Siskiyou Blvd, Ashland, OR 97520, USA

“Roll out mats side by side for a sweat-and-stretch session that leaves them loose, clear-headed, and ready for a relaxed post-class stroll or tea nearby.”

Winburn Way, Ashland, OR 97520, USA

“Stroll hand in hand along shaded paths and ponds, pause on grassy lawns or by the gardens, and trade serves on the tennis or volleyball courts in this 100-acre park off Winburn Way.”

Ashland, OR 97520, USA

“Slip into the shaded trails of Oredson Todd Woods, a rugged, dog-friendly preserve where you can wander side-by-side through quiet pines and oaks, pause at small creek crossings, and enjoy an unhurried loop before heading back into Ashland.”

1667 Siskiyou Blvd, Ashland, OR 97520, USA

“Relax into a warm, spice-scented dining room for comforting North Indian classics and shareable curries, an easygoing spot for an unhurried dinner before a play or stroll through town.”

15 S Pioneer St, Ashland, OR 97520, USA

“Visit this renowned repertory theater for an evening of polished performances, lively pre-show buzz on the plaza, and the shared thrill of applauding world-class acting under Ashland’s artsy, small-town glow.”

281 4th St, Ashland, OR 97520, USA

“Start the morning sharing organic espresso and a flaky pastry in a bright, modern roastery where the hum of grinders and spacious seating make it easy to linger and plan the day.”