Ashland Vacations

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Where to stay in Ashland

Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
Landmark building in Ashland Oregon.

Historic Downtown District

4 out of top 10 points of interest in this area
5/5(137 area reviews)

If you're spending some time in Historic Downtown District, Allen Elizabethan Theatre and Oregon Shakespeare Festival are top sights worth seeing.

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Find the Best Ashland Vacation Packages

Ashland Hotel Deals

Prospero's Flagship Inn

Prospero's Flagship Inn

2.5 out of 5
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is ₩143,377 per night from Jun 16 to Jun 17
₩143,377
₩159,869 total
Jun 16 - Jun 17
includes taxes & fees
8.6/10 Excellent! (1,361 reviews)
"Did not enjoy the virtual kiosk check-in experience."

Reviewed on Jun 13, 2026

Prospero's Flagship Inn
Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is ₩217,114 per night from Jun 29 to Jun 30
₩217,114
₩257,259 total
Jun 29 - Jun 30
includes taxes & fees
8.8/10 Excellent! (1,499 reviews)
"Unfortunately breakfast is not provided nor a voucher. They have a cafe onsite yet no breakfast option. That is a downside."

Reviewed on Jun 14, 2026

Ashland Hills Hotel & Suites
Stratford Inn

Stratford Inn

2.5 out of 5
555 Siskiyou Blvd Ashland OR
The price is ₩209,300 per night from Jun 22 to Jun 23
₩209,300
₩233,369 total
Jun 22 - Jun 23
includes taxes & fees
9.4/10 Exceptional! (1,780 reviews)
"Good location, decent small breakfast, nice bed, bring your wall adapter and cell charger, coffee is weak in breakfast room, Safeway across the street, small TV, non functioning AC"

Reviewed on Jun 13, 2026

Stratford Inn
See all 800 properties in Ashland
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.

Stay near popular Ashland attractions

Photo by Patrick Glassford
Open Photo by Patrick Glassford

Oregon Shakespeare Festival

4.6/5 (620 reviews)
At OSF, America's oldest repertory theater presents Shakespearean classics and bold new works across three venues. Reserve seats for evening performances and arrive early for the free outdoor Green Show entertainment.
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