road trip to ashland, or
This summer, pack your bags and hit the open road—your perfect picturesque escape awaits. Nestled where the Cascade Siskiyou Mountains meet breathtaking wine country, Ashland is the ultimate road trip destination. Filled with small-town charm, rich history, and thrilling outdoor adventure at every turn.
EXCLUSIVE OFFER
15% off Midweek Stay (Sun-Thurs) from May 15 - August 31
Retro Vibes, Small-Town Charm & Big Adventures
Whether you’re rafting heart-pounding rapids, sipping your way through wine country, or enjoying world-class theatre under the stars, Ashland Hills Hotel is your perfect basecamp for it all.
Top Things To Do in Ashland
Rogue River
Enjoy a family-friendly float or chase thrilling rapids—now’s the perfect time to discover one of Oregon’s most spectacular rivers.
Oregon Shakespeare Festival
Experience theatre under the stars, where stories come alive at this Tony Award–winning cultural hub in the heart of Ashland.
Wine Country
Sip your way through the Rogue Valley, where scenic vineyards offer rich reds, crisp whites, and unforgettable views.
Cascade Siskiyou Scenic Bikeway
Explore Ashland and beyond on this scenic 55-mile loop of rolling hills, lush forests, and vineyard-lined landscapes.
Splash into Summer! Stay in Resort-Style Comfort
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Outdoor pool and hot tub
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Fresh eats at Luna Cafe with scenic views and groovy bar
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Tennis and pickleball courts
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Spacious rooms and suites with retro inspired vibes and modern amenities
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Pet approved (A getaway that gives back! In May, 20% of every pet fee is donated to the local Friends of the Animal Shelter)
EXCLUSIVE OFFER
15% off Midweek Stay (Sun-Thurs) from May 15 - August 31
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Best Places to Road Trip
Inspired by wanderlust, fresh air, and good vibes, here are some of the coolest spots in the PNW. From beach bonfires to historic hikes and spa days to seafood feasts—every leg of the journey is a new adventure. We even threw in our suggestions for where to stay at our partner hotels with exclusive discounts as well!
