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Prospero's Flagship Inn

Prospero's Flagship Inn

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
  • 14 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,336 reviews)
"The staff was very helpful and the hotel is close to many things and is not very expensive. For those reasons, we have stayed here before. But you need to know this is not a fancy place. We had some problems with our first room and they upgraded us for free. Things were outdated. However, for the ..."

Reviewed on Jun 5, 2026

Prospero's Flagship Inn
The Bard's Inn, BW Signature Collection by Best Western

The Bard's Inn, BW Signature Collection by Best Western

2.5 out of 5
132 N Main Street Ashland OR
  • 5 min walk from Oregon Shakespeare Festival
Stay at this hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (1,005 reviews)
"Pretty low end"

Reviewed on Jun 4, 2026

The Bard's Inn, BW Signature Collection by Best Western
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
  • 21 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful ...
8.8/10 Excellent! (1,481 reviews)
"It was okay"

Reviewed on May 30, 2026

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
  • 4 min walk from Oregon Shakespeare Festival
Stay at this hotel in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
9.4/10 Exceptional! (1,760 reviews)
"This hotel has parking and is close enough to walk to the plays."

Reviewed on Jun 4, 2026

Stratford Inn
Plaza Inn & Suites at Ashland Creek

Plaza Inn & Suites at Ashland Creek

3 out of 5
98 Central Ave Ashland OR
  • 6 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,008 reviews)
"Definitely recommend. Nice hotel with easy walkable access to Shakespeare Festival and downtown."

Reviewed on Jun 4, 2026

Plaza Inn & Suites at Ashland Creek
Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
212 E Main St Ashland OR
  • 1 min walk from Oregon Shakespeare Festival
Book a stay at this 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! (1,007 reviews)
"Property was clean and maintained well."

Reviewed on Jun 5, 2026

Ashland Springs Hotel
Lithia Springs Resort

Lithia Springs Resort

3 out of 5
2165 W Jackson Rd Ashland OR
  • 4 min drive from Oregon Shakespeare Festival
Stay at this B&B in Ashland. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. ...
9.4/10 Exceptional! (1,006 reviews)
"Mineral water in the room Jacuzzi made it very convenient."

Reviewed on Jun 1, 2026

Lithia Springs Resort
Comfort Inn & Suites Ashland

Comfort Inn & Suites Ashland

2.5 out of 5
434 S. Valley View Rd. Ashland OR
  • 5 min drive from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.8/10 Excellent! (1,006 reviews)
"We came in soooo late but the staff was incredible; so friendly and efficient!"

Reviewed on May 29, 2026

Comfort Inn & Suites Ashland
Timbers INN and Suites

Timbers INN and Suites

2 out of 5
1450 Ashland Street Ashland OR
  • 16 min walk from Oregon Shakespeare Festival
Stay at this motel in Ashland. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8.6/10 Excellent! (1,006 reviews)
"had a nice stay in Ashland. would recommend"

Reviewed on Jun 4, 2026

Timbers INN and Suites
Callahan's Mountain Lodge

Callahan's Mountain Lodge

3 out of 5
7100 Old Highway 99 South Ashland OR
  • 21 min drive from Oregon Shakespeare Festival
Book a stay at this family-friendly lodge in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in ...
8.8/10 Excellent! (1,147 reviews)
"Loved the actual fireplace in the room"

Reviewed on Jun 4, 2026

Callahan's Mountain Lodge
Best Western Windsor Inn

Best Western Windsor Inn

2.5 out of 5
2520 Ashland St Ashland OR
  • 21 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,002 reviews)
"While the decor might seem a little dated, everything about our stay was exceptional. The room was comfortable and functional ( double sinks!) and little things like a working bathroom fan add up to a nice experience. The giant outdoor hot tub with a view of the mountains was a relaxing way to end ..."

Reviewed on Jun 4, 2026

Best Western Windsor Inn
Holiday Inn Express & Suites Ashland by IHG

Holiday Inn Express & Suites Ashland by IHG

2.5 out of 5
565 Clover Lane Ashland OR
  • 22 min walk from Oregon Shakespeare Festival
Book a stay at this business-friendly hotel in Ashland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (1,006 reviews)
"The room was clean, the parking was easy, and the staff was friendly."

Reviewed on Jun 4, 2026

Holiday Inn Express & Suites Ashland by IHG
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.

Find cheap hotels in Ashland

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