As the jailkeeper in Cymbeline so sagely put it, "He that sleeps feels not the tooth-ache." Toothache or no, embrace the blissful ignorance of sleep at these beautiful Ashland inns, then wake up rested to face yet another day of eating, shopping, hiking, theater-going, and Shakespeare-quoting.
We stayed here for a girls trip, and while the major drawback is that it's quite a few miles from the downtown core (which means a cab or DD is in order should you hit a few bars), it's very clean, comfortable, and affordable. It's also right off the highway, for travelers who just want to get to the room after a long drive. And if you happen to be a beer enthusiast, perhaps its greatest selling point is that it's literally just down the street from the big beautiful new Caldera brewery, so if you plan on hanging out there for most of your trip, this is where you should book.
This turn of the century hotel is in the historic railroad district, one of my favorite places to hang out in Ashland, and you can walk easily to cute shops, restaurants, the co-op, Noble's coffeehouse and the yoga studio. There are high end amenities, beautiful gardens, a peaceful setting (you'll sleep well), and an onsite restaurant that's nice for dessert and a drink after you come back from exploring downtown (a 5-10 minute walk, depending on how fast you are).
This darling retro motor inn caught my eye thanks to the pool cabanas--such a cute, classy idea. It's a mile from the downtown core, so you won't be in the heart of the action, but it's an easy walk. You are right across from the University, and very close to the best breakfast spot in town, Morning Glory, and one of the best coffeehouses, Case. Rooms are small and sweet, the grounds are beautiful, and as mentioned, the pool is a highlight.
Lodging can get very expensive in Ashland, especially at the height of tourist season, so this extremely well-located downtown hotel is a nice break for the budget traveler. It's light on luxuries and you'll share a bathroom, but there's a convivial spirit, homey decor, and free internet, plus you'll definitely get flashbacks to your European hosteling days.
Ideal if you want to live like a local (a local who lives really well, that is), this gorgeous bungalow turned B&B is a short walk from downtown but sits a bit up the hill so some of the rooms have great views of the Cascades (all have private bathrooms). Breakfast includes the New York Times and Noble coffee, plus delicious from scratch pastries. Don't forget to ask about your Lillie Belle chocolate shop coupon!
Darling little blue B&B just a few blocks from downtown, in a quiet neighborhood near Ashland Creek Park. Just five rooms and a cute cottage (all with private baths), a sumptuous breakfast (local Noble coffee is served), a pretty back deck and patio for summer evening sipping, and European owners who pride themselves on superb hospitality.
We had such a great stay at this gracious B&B, located just a couple of blocks from both the main street of Ashland and the plaza, and within easy walking distance of the historic Railroad District. The innkeeper is very sweet and accommodating, the rooms are immaculately decorated and very comfortable (get one of the upstairs front-facing ones). and breakfast was delicious. Would stay here again in a heartbeat.
If B&Bs or Best Westerns aren't your thing, you might be having trouble finding Ashland lodging, but this lovely main street hotel is your salvation. With beautiful views, an adjoining restaurant and bar, continental breakfast, free parking, Frette linens and a proper lobby, it's one of the most elegant spots to stay in Southern Oregon.
The owner's of this charming B&B, which is just a short ways from the heart of downtown Ashland, have taken great care with their garden--sit on the deck and read a book with the burbling of the waterfall and koi pond in the background for a peaceful escape from regular life.
My favorite Ashland B&B, this Victorian beauty has lots going for it--quiet but central location, rich decor, lush grounds, and in-house Alchemy restaurant and wine bar (which has a great happy hour, twice daily).