Ashland Holidays
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Our guide on where to stay in Ashland
Find the best Ashland areas and neighborhoods for the activities you enjoy most. Learn more about Ashland
Historic Downtown District
4 out of top 10 points of interest in this area
While visiting Historic Downtown District, you might make a stop by sights like Allen Elizabethan Theatre and Oregon Shakespeare Festival.
Ashland Holiday
Our pick of the best Ashland Hotel Deals
Prospero's Flagship Inn
1193 Siskiyou Blvd Ashland OR
Fully refundableReserve now, pay when you stay
The price is NZ$164 per night from 9 June to 10 June
NZ$164
9 June - 10 June
includes taxes & fees
8.6/10 Excellent! (1,337 reviews)
"Every things was excellent about our stay, the staff, the room, location, etc. except that the shower wouldn't adjust to a comfortable temperature. I did tell the staff about that and fully expect it will be fixed. I have stayed there before and would normally give it 5 stars in all categories."
Reviewed on 5 June 2026
The Bard's Inn, BW Signature Collection by Best Western
132 N Main Street Ashland OR
Fully refundableReserve now, pay when you stay
The price is NZ$257 per night from 8 June to 9 June
NZ$257
8 June - 9 June
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Disappointed in our room air conditioner, that continually shut down and never cooled the room sufficiently. The staff offered to move us, but by that time we were unpacked and had reservations for dinner."
Reviewed on 5 June 2026
Ashland Hills Hotel & Suites
2525 Ashland St Ashland OR
Fully refundableReserve now, pay when you stay
The price is NZ$272 per night from 8 June to 9 June
NZ$272
8 June - 9 June
includes taxes & fees
8.8/10 Excellent! (1,482 reviews)
"Staff was not helpful at all. Had a lot of items to unload and they would not relocate our room or work with us because they said we booked on a third party platform and not on their website. They blamed us for booking on Expedia saying they can’t do anything for us."
Reviewed on 5 June 2026
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.
Discover the most popular places to visit in Ashland
Allen Elizabethan Theatre
You can enjoy a show at Allen Elizabethan Theatre during your trip to Ashland. Wander around the area's picturesque gardens or experience its entertainment choices.
Oregon Cabaret Theatre
You can get tickets for a performance at Oregon Cabaret Theatre during your stay in Ashland. Amble around this family-friendly area's picturesque gardens and enjoy its top-notch restaurants.
What to do in Ashland
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
