Searching for Ashland Oregon hotels? You’re in for a treat. Ashland, Oregon blends cultural gems with natural scenery, so picking the right place to stay really matters.
This small city draws thousands every year. Folks come for the famous Oregon Shakespeare Festival, mountain adventures, and the quirky downtown scene.
I dug into Ashland Oregon hotels and cozy B&Bs so you can find a spot that fits your vibe. From historic inns to charming bed & breakfasts, each one brings something unique for travelers chasing comfort and convenience in Southern Oregon.
1. Grandview of Ashland
Grandview of Ashland sits up in the hills, giving you sweeping mountain views and a modern vacation home feel. If you want peace but still want to be close to Ashland’s best spots, this is a solid pick.
Luxury amenities set this place apart. You’ll get a hot tub, sauna, and outdoor fire pit for those cool Oregon evenings.
There’s a grill and an outdoor shower to help you soak up the Ashland weather. Lithia Park is just five minutes away by car.
The Oregon Shakespeare Festival theaters are close too, so theater buffs will love the location. Free parking and WiFi are included, which is always a plus.
The kitchen and living spaces here feel genuinely homey—sometimes you just want to sprawl out, you know? Check-in starts at 4:00 PM, and checkout wraps up by 10:00 AM.
At least one guest must be 18 or older. Kids of all ages are welcome here.
Other perks include a washing machine, blackout curtains, and a flat-screen TV for downtime. Book your stay at Grandview of Ashland for a luxury mountain retreat that’s still close to the action.
2. Oak Hill Bed & Breakfast
Oak Hill Bed & Breakfast is one of the top-rated Ashland Oregon hotels, with glowing five-star reviews all over travel sites. This intimate inn has just six rooms, each with its own personality, so you get lots of attention from Brian and Anna, the innkeepers.
Southern Oregon University is only two minutes away by car, and North Mountain Park is a quick six-minute drive. You’re right in the middle of things here.
Every morning, they serve a complimentary full breakfast from 8:00 to 10:00 AM. Rooms come with free Wi-Fi, designer toiletries, and daily housekeeping.
There’s a garden terrace, a cozy library, and even ski storage if you’re here in winter. Free parking makes exploring Ashland a breeze.
Check-in is between 3:00 and 6:00 PM, and checkout is before 11:00 AM. Kids seven and up are welcome, but the main guest needs to be at least 21.
Oak Hill Bed & Breakfast is a fantastic base for the Oregon Shakespeare Festival or just soaking in Ashland’s charm. The peaceful vibe and central location make it a favorite for visitors who want the best of both worlds.
3. Country Willows Inn and Estate
Country Willows Inn and Estate sits on five peaceful acres just outside downtown. This bed and breakfast feels rural, but you’re still close to Ashland Oregon hotels and everything the city offers.
There are nine rooms in total, spread across a main house, a separate cottage, and three suites inside a barn from 1896. Four of the rooms are upstairs in the main house, each with a private marble bathroom.
The grounds feature koi ponds, a duck pond, and winding garden trails. During the warmer months, you can take a dip in the seasonal heated outdoor pool.
They even offer onsite massage services if you’re in the mood for extra relaxation. Breakfast is complimentary and served daily from 8:30 to 10:30 AM.
Free WiFi, parking, and concierge services are all included. You’re just a five-minute drive from Weisinger Family Winery and SOU, and downtown Ashland is less than three miles away.
Check-in runs from 3:00 to 6:00 PM, and checkout is before 11:00 AM. Heads up: no kids or pets allowed here.
Want a peaceful retreat with easy access to Ashland Oregon hotels and attractions? Book your stay at Country Willows Inn and Estate.
4. Abigail’s Bed and Breakfast Inn
Abigail’s Bed and Breakfast Inn is one of the last true English-style B&Bs in Ashland. This adults-only spot gives you an elegant escape just a short walk from downtown.
You can stroll to Lithia Park or the Oregon Shakespeare Festival. Built in 1904, the inn shows off original Craftsman architecture and period details in all six rooms.
Rooms come with comfy beds, high-quality linens, and flat-screen TVs. Free WiFi keeps you connected, and the peaceful garden views are a nice touch.
Breakfast is served daily from 9:00 to 9:30 AM for an extra $25 per person. Guests rave about the food and the owners’ hospitality.
Free parking makes it easy to explore the Rogue Valley wine region. The inn has a minimum age of 21 and doesn’t allow kids or pets.
Check-in is from 3:00 to 6:00 PM, and checkout is between 8:00 and 11:00 AM. Book your stay and see why so many people love this Ashland Oregon hotel alternative.
5. Winchester Inn
The Winchester Inn is one of the most iconic Ashland Oregon hotels. This Victorian boutique property mixes historic charm with modern luxury, right in the center of downtown.
There are 21 rooms and suites, each decorated differently. Expect pillowtop beds with Egyptian cotton linens, flat-screen TVs, and designer toiletries.
When you stay here, you’re steps from the Oregon Shakespeare Festival and Oregon Cabaret Theatre. Lithia Park and the Ashland Library are just a quick walk away.
Guests get a complimentary cooked-to-order breakfast each morning from 8:00 to 9:30 AM. There’s also an on-site restaurant and bar if you want dinner or drinks.
Other perks include free WiFi, parking, and concierge services. The inn welcomes kids, but there’s an extra fee for those over eight sharing existing beds.
Check-in starts at 4:00 PM, and checkout is 11:00 AM. They collect a $250 deposit at arrival, which you get back when you leave.
Thinking of a stay at one of the best Ashland Oregon hotels? Book your room at Winchester Inn and see what all the fuss is about.
6. Palm Cottages
Palm Cottages is just steps from Southern Oregon University. This budget-friendly 2-star motel has 16 air-conditioned rooms with modern touches.
Each room includes an iPad and flat-screen TV. Free WiFi keeps you connected, and there’s cable programming for those lazy evenings.
There’s a seasonal outdoor pool if you want to cool off. The garden and picnic area are perfect for a laid-back afternoon, and there’s a terrace for extra seating.
It’s a three-minute drive to Oregon Cabaret Theatre. The Oregon Shakespeare Festival and Thomas Theatre are just over a mile away, and Lithia Park is nearby if you’re craving some nature.
Free parking is included. Express check-out and luggage storage are available, and concierge services can help you plan your stay.
Check-in is from 3:00 to 10:00 PM, and checkout is before 11:00 AM. If you’re arriving late, just let them know in advance.
The main guest must be at least 18. Sorry, no pets allowed at this spot.
Want an affordable option among Ashland Oregon hotels? Book your room at Palm Cottages for a simple, comfortable stay.
Local Attractions & Nearby Activities
Ashland combines world-class theater with serene green spaces, making it ideal for both culture lovers and nature enthusiasts.
Ashland Library, located downtown, offers a quiet retreat with cozy seating, free Wi‑Fi, and community events—perfect for travelers who want to relax or stay connected.
Lithia Park spans about 93 acres from the downtown plaza up Ashland Creek, featuring trails, bridges, duck ponds, tennis courts, a Japanese Garden, and an outdoor bandshell. It serves as a beloved oasis in the heart of the city.
The Oregon Shakespeare Festival runs annually from late April through December, offering roughly 800–850 performances in three theaters. The program mixes Shakespearean classics and modern plays, with educational tours and pre-/post-show talks.
Momentum River Expeditions and Noah’s River Adventures offer rafting trips on the Rogue River and nearby waterways in Southern Oregon and Northern California. Options range from exhilarating whitewater to peaceful float trips, best enjoyed in spring and early summer.
Jackson Wellsprings, just a few miles outside Ashland, is a wellness haven set on natural mineral springs. With multiple pools, tranquil garden grounds, hiking paths, day passes, camping, and spa services, it’s perfect for visitors seeking rejuvenation.
Comparison & Recommendation: Ashland Oregon Hotels
Oak Hill Bed & Breakfast offers the best value at $249 per night, with a 9.9 rating. If you’re searching for Ashland Oregon hotels that balance price and comfort, this one’s hard to beat.
Palm Cottages gives you the most budget-friendly option at $203 nightly. For travelers who care about savings but still want charm, it’s a solid pick among Ashland Oregon hotels.
Grandview of Ashland tops the list with a perfect 10.0 score, though it comes at $323 per night. Winchester Inn falls into the premium range at $319, with a respectable 9.5 rating.
| Traveler Type | My Recommendation | Why |
|---|---|---|
| Budget-conscious | Palm Cottages | Lowest price at $203 |
| Best value seekers | Oak Hill B&B | High 9.9 score for $249 |
| Luxury travelers | Grandview of Ashland | Perfect 10.0 rating |
For downtown access to theaters and shopping, I’d steer you toward Winchester Inn. It’s right in the action and still delivers on quality.
If you’re after a quiet, intimate experience, Oak Hill Bed & Breakfast and Country Willows Inn both shine with peaceful settings and personal service. Honestly, it’s hard to pick just one.
Families will probably get the most out of Palm Cottages thanks to the lower costs and those cottage-style accommodations. Couples who want a little romance should look at Abigail’s Bed and Breakfast Inn—the atmosphere is genuinely charming.
If you’re a pet owner, don’t forget to call Ashland Oregon hotels directly about pet policies. Bed and breakfasts can have some pretty specific restrictions, and there’s nothing worse than showing up and getting turned away.
Ashland Oregon Hotels Detailed prices and ratings
| Hotel | Score (out of 10) | ★‑Rating | Price (USD per night, double) | Booking Link |
|---|---|---|---|---|
| Grandview of Ashland | 10.0 | ★★★★ | $323 | Book Now |
| Oak Hill Bed & Breakfast | 9.9 | ★★★ | $249 | Book Now |
| Country Willows Inn and Estate | 9.8 | ★★★ | $282 | Book Now |
| Abigail’s Bed and Breakfast Inn | 9.8 | ★★★ | $285 | Book Now |
| Winchester Inn | 9.5 | ★★★ | $319 | Book Now |
| Palm Cottages | 9.2 | ★★ | $203 | Book Now |
| * Prices do not include taxes and fees. Rates are subject to change daily. Please refer to the actual booking page for up‑to‑date availability and pricing. | ||||
